There is a strange thing that happens when people become responsible for other people: they start feeling as though they’re supposed to know more than they do.

It makes sense. We promote people because they have experience. Founders are expected to have conviction. Executives are paid to make decisions. When something goes sideways, nobody calls a meeting because they want to watch the person in charge shrug and say, “I have no idea.” Leadership comes with an expectation of answers, and over time that expectation can turn into a habit. We get very good at answering quickly, defending what we already know, and moving everybody toward a decision.

The problem is that speed and certainty aren’t the same thing as good judgment.

A lot of expensive business mistakes begin with an answer that arrived too early. We assume the customer left because of price. We assume the employee isn’t performing because they don’t care. We assume sales are down because marketing isn’t working. We assume a competitor is winning because they have a better product. Once the explanation feels plausible enough, the organization starts moving around it. Meetings happen. Budgets change. People get hired or fired. New software gets purchased. Sometimes the original assumption was right. Sometimes we just built an impressive response to a problem we never actually had.

That distinction matters even more now because answers have become extraordinarily cheap. AI can give you ten strategies before you’ve finished your coffee. It can summarize the meeting, analyze the spreadsheet, draft the plan, challenge the plan, and produce another version when you don’t like the first one. The bottleneck is increasingly not access to an answer. It’s knowing whether you’re asking a useful question in the first place.

Curiosity, in that environment, starts looking less like a personality quirk and more like management infrastructure.

And apparently a lot of workplaces could use more of it. SurveyMonkey’s 2026 State of Curiosity research found that while 95% of surveyed workers described themselves as at least somewhat curious, only 30% said their workplace strongly rewards curiosity. Their research points toward a pretty uncomfortable possibility: companies may employ plenty of curious people while creating systems that quietly train the curiosity out of them.

That tension is what made my recent conversation with Jon Beebe on Eggs! The Podcast interesting. Jon calls his approach “curiosity-driven leadership,” built around a progression from curiosity to connection to community. jon-ryan What caught my attention wasn’t the framework itself so much as what sits underneath it: the idea that leadership improves when we become a little less interested in immediately proving what we know.

From Answers to Investigation

Jon Beebe spent fourteen years in ministry before moving full-time into entrepreneurship and the businesses he runs with his wife, Lauren. Along the way, he discovered that what he had initially understood as pastoral work was also leadership work: recruiting people, building teams, creating systems, developing volunteers, and building communities people actually wanted to remain part of.

Today, he brings that experience into his work around curiosity-driven leadership while continuing to operate Beebe’s Bargains, the family business that grew from Lauren’s deal-finding hobby into a staffed operation focused on helping families save time and money. Jon’s own company history describes the business as beginning with a Facebook group in 2018 before developing into a full-time operation.

What makes his perspective useful here is that he treats curiosity as something you do, particularly when your first instinct is to react.

Three Questions Worth Carrying Into Work

Jon's framework gets especially useful when it moves out of theory and into ordinary management situations. Three ideas from our conversation stood out.

1. Stop writing the story before you’ve reported it.

“Don’t tell yourself a story in your head about they’re saying this because they think this, this, and this... be a journalist. Really investigate.”

There may not be a more common management error than confusing an interpretation with a fact.

Someone misses a deadline and we decide they’re disengaged. A customer goes quiet and we decide the deal is dead. An employee pushes back and we decide they have an attitude problem. Pretty soon we’re responding not to what happened, but to the little screenplay we’ve written about why it happened.

Actionable insight: Jon’s journalist-versus-fiction-writer distinction is useful because it gives the leader another job: investigate before interpreting. What happened? What am I missing? What does the other person know that I don’t?

You may arrive at exactly the same conclusion. The difference is that you’ve earned it.

2. Better questions can change the size of the solution.

“The better question you ask will get you a better answer or get you a different answer.”

Jon uses a simple example in the conversation. If your car keeps breaking down, you can ask how you’re going to pay to repair it. That’s a perfectly reasonable question, and answering it solves the immediate problem. But you could also ask how you’re going to afford a different car.

Same breakdown. Different question. Different range of possible answers.

Actionable insight: Businesses do this constantly. “How do we get more leads?” produces one category of work. “Why aren’t more of the right customers choosing us?” produces another. “Who should we hire?” is different from “Why does this job require another person at all?”

Before putting more effort into an answer, it may be worth examining the question that’s generating it.

3. Put the leadership problem back on the leader first.

“We need to say, ‘I haven’t led them to do it yet.’”

I like this one because it’s uncomfortable.

Jon’s point isn’t that every performance problem is secretly the manager’s fault. Some people are wrong for a role. Some won’t do the work. Some eventually need to leave.

But “they won’t do it” closes the investigation. “I haven’t led them to do it yet” keeps it open a little longer.

Actionable insight: Maybe the expectation wasn’t clear. Maybe the person needs a different kind of instruction. Maybe they’re excellent but sitting in the wrong seat. Maybe the system around them makes success unnecessarily difficult. Or maybe, after looking carefully, you discover that they really aren’t right for the job.

The value is not avoiding accountability. It’s making sure the leader participates in it.

Certainty Is Useful.
So Is Knowing When to Distrust It.

Leadership still requires decisions. Eventually somebody has to stop asking questions and choose a direction. Curiosity without action can become its own kind of avoidance, and businesses don’t get very far if every decision remains permanently open for discussion.

But I suspect most organizations have the opposite problem.

We reward decisiveness because it’s visible. The person who speaks confidently in the meeting looks like they’re leading. The person who says, “I’m not sure that’s actually the problem” can look like they’re slowing everybody down. Under enough pressure, the incentive becomes obvious: answer first, investigate later.

That’s dangerous when technology can now manufacture convincing answers almost instantly.

The advantage may increasingly belong to leaders who know where to insert friction: one more question before the strategy, one more conversation before the judgment, one more attempt to separate what happened from the story we’ve attached to it.

The goal isn’t to become less decisive. It’s to become harder to fool—including by ourselves.

Thanks for reading.
—Ryan

The Lid - The Invisible Barrier Between Here and What’s Next

My new book, The Lid, is coming November 3. It’s about the wall you keep hitting: the work grows, momentum builds, and then, just short of the thing you were reaching for, you stop. Same place, every time. The Lid names what’s stopping you and lays out the moves that actually shift it. It isn’t a book about thinking differently. It’s a book about moving when you don’t know how.

The Kindle edition is available to pre-order now. If you’d rather read some of it first, the opening chapter is free at thelidbook.com.

Pre-order the Kindle edition →

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Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

1. The Bezos Letters — Steve Anderson and Karen Anderson

   Jon mentions Steve Anderson and The Bezos Letters during the conversation while discussing the difference between improving what already exists and creating something genuinely different. The book draws lessons from Jeff Bezos’s shareholder letters and organizes them around testing, building, accelerating, and scaling—making it a useful companion to this week’s argument about curiosity, experimentation, and the questions that precede growth.

Listen In/More to Explore

1. Eggs! The Podcast — Episode 483
   Curiosity-Driven Leadership with Jon Beebe

2. Follow Jon’s work
   Jon Beebe on LinkedIn

   Beebe’s Bargains

There has never been a better time to be an exceptionally productive entrepreneur. At least that’s what the technology industry keeps telling us. AI can write our proposals, summarize our meetings, conduct research, build software, manage communications, and automate an increasingly impressive collection of administrative tasks. A business that once required ten people might now operate with five. In some cases, perhaps even fewer. The economics are compelling, and the opportunity is real. But there’s a problem with the way we’re measuring all this newfound efficiency: we’re getting remarkably good at accelerating work without necessarily changing who remains responsible for getting it done.

Consider what happens when a founder introduces a new automation into an already overloaded business. The automation handles a repetitive task, which is great. But someone still needs to configure it, monitor the results, resolve exceptions, maintain the integrations, and make decisions when something unexpected happens. In small to mid-sized operations, that someone is often the founder. The same thing happens when we hire another employee without establishing clear ownership. We’ve increased the organization’s capacity while simultaneously creating another relationship that requires our attention. Individually, these decisions make sense. Collectively, they can produce a company that accomplishes considerably more while remaining just as dependent on the person who started it.

The distinction matters because productivity and organizational independence are two different things. A founder might use AI to produce an entire week’s worth of marketing materials in an afternoon, but if every campaign still requires their approval, they’ve accelerated production without fundamentally improving the operating model. The same applies to customer service, project management, financial administration, and virtually every other business function. Eventually, the limiting factor becomes the founder’s capacity to make decisions, provide direction, and review completed work. You can only accelerate the machinery so much before the person operating it becomes the constraint.

And the current enthusiasm around AI makes this particularly interesting. Research from JPMorganChase shows that small-business AI adoption is accelerating, although adoption remains uneven across companies and industries.

The opportunity to operate more efficiently is expanding, but technology alone doesn’t establish accountability or decide which work deserves human attention. Those are management problems. An organization without clear responsibilities, reliable processes, or the authority to make routine decisions will carry those weaknesses into whatever technology it adopts. It may simply discover new ways to experience them.

I think there’s a useful way to evaluate progress here. Instead of asking how much more work the business can produce, examine how much of that work can move forward without the founder’s involvement. Can someone else resolve a routine customer issue? Does the team know what happens when a deadline changes? Can a project continue when the owner is unavailable? These questions reveal what productivity metrics often miss: whether the company is building its own operating capacity or simply extending the reach of one particularly busy person.

That distinction sits at the center of my recent conversation with Kris Ward on Eggs! The Podcast. Kris has spent years helping entrepreneurs address the operational problems that keep them working excessive hours. Her perspective is particularly relevant now because she challenges one of the most familiar solutions to founder overload: simply handing more work to somebody else.

From Software to Supply Chains

Kris Ward is a team-building and systems strategist, author, podcaster, and coach whose approach to business operations emerged from a deeply personal experience. After spending the early years of her business working extraordinarily long days, she began restructuring the way she managed her time and team. She describes eventually reducing her working day from sixteen hours to six.

That work became particularly important when her husband was diagnosed with colon cancer. Kris says she spent much of the following two years away from her business while supporting him through his illness. Because of the systems and team she had established, her existing clients were largely unaware of her absence. After her husband’s passing, other entrepreneurs began asking how she’d managed it. Those conversations eventually helped shape her work teaching founders to build businesses that don’t require their constant involvement.

Her experience raises an important question about the relationship between business ownership and personal freedom: what does it actually take to make yourself less essential to the company you’ve created?

Three Things That Change the Equation

Kris's approach challenges several assumptions about how founders should manage their businesses. Three observations from our conversation are especially relevant to entrepreneurs trying to build more capable organizations.

1. Delegation can preserve the very problem you’re trying to solve.

“I think delegation is a lateral move at best. The work still has to come through you.”

The important distinction here is between assigning work and transferring responsibility. If someone completes a task but requires you to explain every step, answer routine questions, review the result, and determine what happens next, you’ve transferred the execution without transferring much of the responsibility.

There are circumstances where that arrangement is appropriate. High-risk decisions, sensitive customer relationships, and work requiring specialized judgment deserve oversight. But applying the same management model to every routine activity creates an unnecessary operational burden.

Actionable insight: Identify one recurring process that requires your approval. Examine which decisions genuinely require your judgment and which could be handled independently with clearer expectations, defined boundaries, and an agreed escalation procedure. The objective isn’t eliminating oversight. It’s making oversight proportional to the actual risk.

2. More people won’t compensate for a broken operating model.

“Adding more people to chaos does not create calm.”

Hiring often feels like the obvious response to an overwhelming workload. But a new employee inherits the operating environment you already have, including its undocumented procedures, unclear priorities, and inconsistent communication.

Kris advocates what she calls Super Toolkits: concise, continuously updated process documents designed to help team members execute work independently. Her argument is that traditional operating manuals frequently become too cumbersome to maintain or use.

Actionable insight: Before adding another employee or AI-powered workflow, document how one important process actually operates. Identify its starting point, the person responsible, the information required, the expected outcome, and the circumstances that warrant escalation. Then have someone else follow the process. The difficulties they encounter will tell you considerably more about your operational readiness than another software subscription.

3. Automation still requires operational ownership.

“Somebody has to check the automations.”

Kris makes this observation during our discussion about AI and virtual assistants. Her position isn’t that entrepreneurs should avoid automation. It’s that someone needs to take responsibility for maintaining it.

This is particularly relevant as increasingly sophisticated AI tools become available to smaller businesses. Automating an inefficient process doesn’t necessarily improve the underlying process, and a system that works perfectly under normal conditions can still create problems when something unexpected happens.

Actionable insight: Treat every significant automation as an operational responsibility rather than a completed installation. Establish who owns it, how its performance will be checked, what happens when it fails, and which decisions require human intervention. The goal is to create systems that reduce the founder’s workload without creating an entirely new category of work that only the founder can manage.

Build for the Day You're Not There

One of the more revealing aspects of Kris’s story is that she didn’t originally restructure her business in anticipation of a family emergency. She was trying to reclaim a reasonable working life. The changes she made eventually allowed her to be present during a period when her attention was needed somewhere far more important than the office.

That experience suggests a useful standard for evaluating the businesses we’re building. A company’s ability to function without its founder shouldn’t become relevant only when someone is preparing for an acquisition, planning a vacation, or confronting an unexpected personal crisis. It’s a measure of organizational maturity that deserves attention throughout the business's life.

AI introduces some remarkable possibilities here. Small teams can accomplish things that previously required substantially greater resources. But the real opportunity may lie in combining that technological capacity with better organizational design. Clear responsibilities, capable people, dependable processes, and appropriate automation can create an operating environment where the founder’s attention becomes available for the work that genuinely requires it.

There’s a meaningful difference between building a company that can do more and building one that can do more without constantly needing you. The second requires a little more thought, but it creates something that productivity alone cannot provide: the freedom to decide where your attention belongs.

Thanks for reading.
—Ryan

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Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

1. Win The Hour, Win The Day — Kris Ward

   Kris’s book is a natural companion to this week’s discussion. It expands on her approach to time management, building a support team, and developing the processes that allow entrepreneurs to step away from routine work. Particularly relevant for readers who recognize the founder bottleneck but haven’t established a practical way to address it.

   Book link to be added after confirmation.

Listen In/More to Explore

1. Eggs! The Podcast — Episode 481
   Getting out of the Middle: Overcoming the Founder Bottleneck with Kris Ward

2. Explore Kris's approach to building independent teams and developing operational systems at Win The Hour Win the Day

For most of my adult life, the safest career advice sounded something like this: get educated, learn to work with information, and move as far away from manual labor as you can. The future belonged to knowledge workers. The people who could analyze, strategize, communicate, design, code, manage, and make decisions would have the leverage. Physical work would eventually be automated, outsourced, or pushed down the economic ladder — AI is starting to make that assumption look shaky.

The first jobs being meaningfully compressed by AI aren’t electricians, machinists, welders, HVAC technicians, or the people building semiconductor fabs and pharmaceutical plants. They’re writers, analysts, programmers, designers, researchers, marketers, and plenty of other people whose careers were built around producing and manipulating information. A huge amount of work that once required a reasonably expensive human being can now be done faster, cheaper, and often surprisingly well by software. That doesn’t mean those professions disappear. It does mean the economics around them start to change.

At the same time, the physical economy is running into a very different problem: scarcity. We need people who can actually build things. Data centers need electricians. Semiconductor facilities need highly trained technicians. Pharmaceutical manufacturing requires clean rooms, specialized equipment, quality systems, maintenance, logistics, and an enormous amount of infrastructure. These aren’t the old factory jobs people picture when someone says “blue collar.” Many of them are highly technical, highly specialized, and increasingly hard to staff.

That creates an interesting inversion. Intelligence is getting cheaper. Physical capability is getting more valuable.

I can already see pieces of this in my own work. AI has allowed me to do things that would have required an entire team not very long ago. I can prototype software, work through technical problems, generate research, test positioning, build systems, and move ideas much further on my own before I need outside help. That is an incredible advantage, but it also means the market needs fewer people to produce the same amount of intellectual output. Multiply that across millions of businesses and it becomes pretty obvious why the old white-collar premium may not hold the way we once assumed it would.

Meanwhile, somebody still has to build the factory. Somebody has to wire the data center, install the equipment, maintain the machines, manufacture the drugs, move the materials, and make the physical world work. Robots will eventually take on more of that too, but “eventually” matters. Software can spread almost instantly. Rebuilding the physical economy takes years, enormous amounts of capital, and a workforce we haven’t spent nearly enough time developing.

That tension came up repeatedly in my recent conversation on Eggs! The Podcast with Tony Paquin, founder and CEO of iRemedy. Tony has spent roughly four decades building technology companies, working across software, healthcare, and global supply chains. His view is that we may be moving out of an economy organized primarily around information and into something much more physical: a production economy where manufacturing, infrastructure, energy, and skilled labor become increasingly valuable precisely because AI is making so much knowledge work abundant.

From Software to Supply Chains

Tony Paquin has spent roughly four decades building technology companies, often in markets that were on the verge of significant change. He started as a programmer almost by accident, writing software for an insurance agency after deciding that a $50,000 software package seemed excessive for a small business. That project eventually grew into a major insurance-software company. Later, he built a web-based electronic medical records business that went public on Nasdaq, pulling him deeper into healthcare and setting the stage for much of the work that followed.

After leaving that company, Tony began consulting with hospitals and ultimately worked with roughly 600 across the country. His work increasingly centered on what he called “retail healthcare” and eventually on building and operating hospital pharmacies. That experience exposed him to a problem that would become central to his career: the enormous complexity and fragility of the global healthcare supply chain. Today, he is the founder and CEO of iRemedy, a healthcare supply company that uses technology and AI to monitor global manufacturing, sourcing, and supply-chain risk.

That work became especially consequential during COVID. Working with the federal government, Tony and his team helped source needles and syringes for the vaccination effort, ultimately chartering 135 Boeing 747s and importing roughly 1.2 billion medical items. The experience put him on the front lines of the global competition for critical medical supplies and later became the basis for his book, The End of Us. It also gave him a particularly unusual vantage point on what comes next: a technologist who has spent his career building software, but who now sees manufacturing, infrastructure, and skilled physical work becoming increasingly important in an AI-driven economy.

Where the Value Is Moving

Tony’s argument isn’t that white-collar work disappears or that everyone should suddenly learn a trade. It’s that AI is changing what’s scarce—and scarcity has a funny way of changing what the market is willing to pay for.

“This economy is gonna switch from the information age to the production age.”

Actionable insight: Pay attention to where capital is moving, not just where the headlines are. The next wave of opportunity may be less about producing more information and more about the infrastructure, manufacturing, energy, logistics, and specialized labor required to turn ideas into something physical.

“If you were to go blue collar versus white collar, which one makes more money? Everybody would immediately go, the white collar guy does... That’s not going to be true much longer.”

Actionable insight: Old assumptions about career value are exactly that: assumptions. Whether you’re building a company or advising your kids about careers, it’s worth looking at actual supply and demand instead of relying on the hierarchy of jobs we inherited from the last economy.

“The blue collar people are gonna see their salaries double, triple, and quadruple while they find their niches in the market.”

Actionable insight: The opportunity isn’t necessarily in generic labor. It’s in specialization. The people who understand sophisticated equipment, clean rooms, advanced electrical systems, automation, precision manufacturing, or other difficult physical systems are building expertise that cannot be copied and distributed at the speed of software.

“These aren’t like dirty, low-paying jobs... building these data centers, building a pharmaceutical manufacturing company is going to be sophisticated. These are going to be good quality jobs.”

Actionable insight: We may need to update the picture in our heads when we hear “manufacturing.” A modern semiconductor fab, pharmaceutical plant, or AI data center bears very little resemblance to the industrial-era factory floor most people imagine. The work has changed, and perception is lagging behind.

“I’m gonna use it as a force multiplier, but I gotta have a basic force to multiply.”

Actionable insight: AI becomes far more useful when it sits on top of real expertise. Knowing your craft gives you something to challenge the machine with—judgment, context, taste, experience, and the ability to recognize when the answer looks convincing but is wrong.

“They’re not thinking for themselves anymore. They’ve just handed it over to Claude. That’s weak and lazy.”

Actionable insight: There’s a huge difference between increasing your capacity and outsourcing your judgment. If AI is doing the thinking instead of helping you think, efficiency may go up while your actual value goes down.

“I think there’ll be more opportunity created in the next five years than the last twenty-five years.”

Actionable insight: The useful response to disruption isn’t panic, and it isn’t pretending nothing is changing. It’s getting close enough to the change to see where new constraints, shortages, and unsolved problems are appearing. Opportunities usually show up first there.

The Advantage Goes to the Adaptable

The mistake would be to read all of this as a simple contest between white-collar and blue-collar work. It isn’t. The deeper shift is that technology keeps changing what the market considers scarce, and scarcity is what creates value. For decades, access to information and the ability to process it were scarce enough to command a premium. AI is making both dramatically more abundant.

That means the advantage increasingly belongs to people who can combine judgment, expertise, and adaptability with things that remain difficult to automate. Sometimes that will mean knowing how to build, fix, manufacture, or operate something in the physical world. Sometimes it will mean having enough domain expertise to use AI better than everyone around you. In either case, the common denominator is the same: you have to bring something meaningful to the machine. Tony’s point about needing “a basic force to multiply” may be one of the most useful ways to think about what comes next.

We’ve been through technological transitions before, and they rarely reward the people who spend the most time arguing about whether the change should be happening. They reward the people who understand where the change is creating new problems, new shortages, and new forms of demand. AI will undoubtedly eliminate some work, reshape a lot more, and create opportunities we can’t fully see yet. The useful question isn’t whether the old rules are changing. They clearly are. It’s whether we’re paying close enough attention to notice where the new ones are being written.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

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Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. The End of Us: A Story of Death, Deception and China’s Deadly Grip on US Healthcare — Tony Paquin
   Tony’s newest book grows directly out of the experience he described on the show: sourcing enormous quantities of medical supplies during COVID and seeing firsthand how dependent the United States had become on overseas manufacturing. Part supply-chain exposé and part real-world thriller, it offers useful context for the larger argument that domestic production is becoming a strategic issue, not simply an economic one.

2. The Retail Healthcare Revolution — Tony Paquin
   Written much earlier in Tony’s career, this book captures another moment when he saw an established industry beginning to change underneath itself. The focus is healthcare consumerism rather than AI or manufacturing, but it’s an interesting companion to this week’s conversation because it shows the pattern Tony has followed for decades: identify where technology is changing the economics of an industry, then get there early.

3. Shop Class as Soulcraft — Matthew B. Crawford
   This one feels almost eerily well suited to this week’s theme. Crawford challenges the long-standing assumption that knowledge work is inherently more valuable than skilled manual work and makes the case for craftsmanship, technical competence, and actually knowing how to make and fix things. It was written well before the current AI boom, which may make its argument even more relevant now.

4. The Coming Wave — Mustafa Suleyman with Michael Bhaskar
   Suleyman, a co-founder of DeepMind and now CEO of Microsoft AI, looks at the extraordinary speed with which AI and other powerful technologies are developing—and the economic, political, and institutional problems that come with trying to control them. If Tony’s argument describes where work may be heading, this book helps explain the technological force pushing it there.

5. The Technology Trap — Carl Benedikt Frey
   Frey takes the much longer historical view, examining what previous waves of automation actually did to workers, wages, political power, and economic opportunity. It’s a useful antidote to both AI utopianism and AI panic: technological progress can create enormous prosperity while still producing very uneven consequences along the way.

More to explore

Learn more about our featured guest — start here:

iRemedy Healthcare — Tony’s healthcare distribution and supply-chain intelligence company, combining direct distribution with AI-powered procurement and supply-chain monitoring. Visit iRemedy Healthcare

The End of Us — Learn more about Tony’s book on America’s dependence on foreign medical manufacturing and the supply-chain vulnerabilities he encountered firsthand. Explore The End of Us

The Supply Side Podcast — Tony’s show exploring healthcare supply chains, reshoring, national security, pharmaceutical infrastructure, and related issues. Listen to The Supply Side on Spotify

Tony Paquin on LinkedIn — Follow Tony for his writing and commentary on AI, healthcare, manufacturing, supply chains, and entrepreneurship. Connect with Tony on LinkedIn

iRemedy Publications & Newsroom — More of Tony’s writing, podcast appearances, Senate testimony, company updates, and research on the healthcare supply chain. Explore iRemedy’s publications

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There comes a point in almost every entrepreneurial business where the founder starts saying some version of the same thing: I need help.

Usually, this realization arrives long after help was actually needed. The inbox is overflowing. Projects are backing up. Sales opportunities are getting less attention than they deserve. Administrative work has somehow colonized entire afternoons. You know you shouldn’t be doing all of it anymore, but every attempt to hand something off creates a new problem. Someone asks a question. You answer it. They ask another. Eventually you decide it would have been faster to do the damn thing yourself.

For a long time, I assumed this was mostly a hiring problem. Find better people. Hire someone more experienced. Get somebody who can “take ownership.” After spending the better part of 20 years running businesses with myself somewhere near the center of the machinery, I’m increasingly convinced that explanation is incomplete. Sometimes the employee isn’t the problem. Sometimes the founder has simply built a company that nobody else knows how to operate.

That distinction matters. There’s a huge difference between knowing how to perform a task and knowing how to explain the system behind it. Entrepreneurs become unusually good at the former because repetition creates instinct. We know which client needs a phone call instead of an email. We know which number in the report actually matters. We know how far we can push a vendor, what a good lead looks like, where a project usually goes sideways, and which exception to make because we’ve seen this movie before. Eventually all of that judgment gets compressed into something that feels obvious. To us.

Then we hire someone and discover that “obvious” is a terrible operating procedure.

I’ve run headfirst into this in my own work. As I’ve tried to move myself farther from the center of the businesses I’m building, I’ve had to confront how many processes I understand perfectly but have never actually documented. I can tell someone I want them to take something over, but when they start asking reasonable questions—What does good look like? When should I escalate this? Which part matters most?—I sometimes realize the complete answer has existed only in my head. That isn’t delegation. It’s handing someone a destination without giving them a map.

And this is where founders can be a little unfair. We complain that people don’t “get it.” We redo their work. We decide nobody cares as much as we do. Occasionally that’s true. Plenty of bad hires exist. But if five smart people have struggled with the same responsibility, it may be time to stop blaming the sixth person you haven’t hired yet. The problem might be the role, the process, the expectations—or the founder who hasn’t made any of those things clear enough to survive without constant intervention.

Effective delegation is more about transforming your knowledge into something others can take ownership of, rather than simply relinquishing control. It involves clarifying desired results instead of assigning tasks haphazardly. It requires discerning what needs your judgment and what can follow a process. Perhaps most challenging, it means accepting that others might achieve the outcomes differently than you would. If your business relies on every decision passing through you, you’ve created dependence instead of leverage.

That tension came up repeatedly in my recent conversation on Eggs! The Podcast with Chris McShanag, founder and CEO of Virtual Teammate. Chris has spent years helping healthcare practices and other businesses rethink how work gets distributed across teams. His argument is simple, but it lands differently when you’ve lived the problem: before you worry about finding the right person, you need to get much clearer about what that person is actually supposed to own—and whether you’ve created a business they can succeed inside.

Building a Business Beyond the Founder

Chris McShanag has spent much of his career thinking about how companies grow—and what gets in the way when they try. Originally from Australia, he began his career with IBM before moving into a company that eventually went through an IPO and acquisition. Entrepreneurship was already familiar territory; his father owned a metal recycling company, and Chris credits both his father and grandfather with shaping his belief in controlling his own destiny and surrounding himself with capable people.

That path eventually led him into healthcare consulting, where he worked with health systems, hospitals, and medical practices on technology and process improvement. But a pattern kept surfacing. Better software and better processes could only go so far when doctors, dentists, and practice leaders were still struggling to find good people—and spending too much of their own time on work that pulled them away from patients and higher-value responsibilities.

Chris ultimately sold his consulting business and founded Virtual Teammate, a global remote staffing company focused primarily on healthcare. Today, the company helps medical, dental, and veterinary practices build teams around clearly defined outcomes, pairing remote professionals with the administrative and operational work that doesn’t require the founder—or the physician—to remain at the center of everything.

Where Delegation Actually Begins

Delegation gets easier once the work is clear. Chris kept returning to the same idea throughout our conversation: before another person can take ownership, the founder has to define what success actually looks like.

“I think the biggest mistake we see is they try and improve or accelerate a process that isn’t quite working.”

Actionable insight: More people won’t fix a broken system. Before you hire, outsource, or automate anything, make sure the underlying process is worth scaling in the first place.

“I’m a big proponent of focusing on outcomes, not necessarily job descriptions.”

Actionable insight: A list of responsibilities tells someone what to do. A clear outcome tells them what they’re responsible for accomplishing. That difference creates far more room for real ownership.

“You can’t do everything by yourself. You can’t be the driver, the pit stop, and everything.”

Actionable insight: Founders often confuse involvement with control. A business becomes more durable when critical work belongs to capable people rather than depending on one person to keep every part moving.

“If it’s urgent and important, that’s the best thing for the founder. If it’s urgent and maybe not important, that’s the best thing to be delegating.”

Actionable insight: Delegation shouldn’t begin with whatever you dislike doing. Start by identifying the work that consumes your time without requiring your judgment, relationships, or unique expertise.

“How many of your hundred-dollar resources are doing ten-dollar tasks?”

Actionable insight: The real cost of low-value work isn’t the hourly rate attached to it. It’s what your best people aren’t doing while their time is being spent somewhere else.

“If you don’t replicate yourself or really bring people along, then you can only go so far.”

Actionable insight: Scale begins when knowledge stops belonging exclusively to the founder. Processes, judgment, expectations, and standards have to become transferable if the company is ever going to grow beyond one person’s capacity.

“Don’t feel like you’ve got to do it all yourself.”

Actionable insight: There’s a point where self-reliance stops being an entrepreneurial strength and starts becoming a constraint. The next stage of growth usually requires letting other capable people carry meaningful parts of the load.

You Don’t Scale by Staying Essential

There’s a strange contradiction at the heart of entrepreneurship. In the beginning, being indispensable is often exactly what makes the business work. You know the customer best. You make the calls. You solve the problems. You hold the thing together. But if that remains true forever, the strength that helped build the company eventually becomes what limits it.

The goal isn’t to disappear from the business. It’s to become more selective about where your presence actually matters. Some decisions need your judgment. Some relationships need your attention. Some work genuinely belongs with you. The rest needs to become clear enough, documented enough, and trusted enough to live somewhere else.

That shift is uncomfortable because it asks founders to give up a little control in exchange for something more valuable: capacity. And if you can create that capacity without losing the standards, judgment, or culture that made the business work in the first place, that’s when the company finally starts becoming bigger than the person who built it.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Buy Back Your Time — Dan Martell
   Chris specifically referenced Martell’s framework during our conversation, and it fits this week’s theme almost perfectly. The premise is straightforward: founders shouldn’t spend their limited time doing work that someone else can own. Martell gets practical about delegation, hiring, and creating enough space for leaders to concentrate on the work that actually requires them.

2. The E-Myth Revisited — Michael E. Gerber
   A classic for a reason. Gerber examines the trap of building a company that depends entirely on the person who started it and makes the case for creating systems that allow the business to operate consistently without the founder personally touching everything. It’s remarkably close to the problem at the center of this week’s essay.

3. Who Not How — Dan Sullivan and Benjamin Hardy
   When entrepreneurs encounter something they don’t know how to do, the instinct is often to learn how to do it themselves. Sullivan and Hardy argue for a different question: who already knows how? It’s a useful shift for anyone discovering that personal capability and organizational scalability are two very different things.

4. Clockwork — Mike Michalowicz
   If the business stops when you stop, you still have work to do. Clockwork gets into the practical side of designing roles, transferring responsibilities, and creating an organization that doesn’t need the owner constantly intervening to keep things moving. For founders who recognize themselves in this week’s essay, this one is particularly relevant.

More to explore

Learn more about our featured guest — start here:

Virtual Teammate — Learn more about Chris’s remote staffing company and its work with healthcare, dental, and other organizations.
Visit Virtual Teammate

Chris McShanag on LinkedIn — Follow Chris for his writing and insights on leadership, delegation, remote staffing, healthcare operations, and building stronger teams.
Connect with Chris on LinkedIn

Virtual Teammate on LinkedIn — Follow the company for practical content on remote teams, healthcare staffing, delegation, and operational capacity.
Follow Virtual Teammate on LinkedIn

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

For most of my career, attention has been treated like the scarce resource. Marketing departments bought it. Agencies fought for it. Brands measured it in impressions, clicks, ratings, open rates, share of voice and, eventually, whatever new metric the latest platform decided mattered. The underlying assumption was always pretty simple: if enough people see you, some useful percentage of them will eventually care.

That equation has changed. Attention isn’t exactly scarce anymore. Given enough money, persistence, or willingness to feed the algorithms, almost anyone can get in front of an audience. A founder can manufacture a steady stream of LinkedIn posts before breakfast. A small company can produce advertising that would have required a full creative team a decade ago. AI can generate articles, video, images, sales copy, and entire campaigns faster than most of us can decide whether any of it is worth making. We solved a large part of the distribution problem. In the process, we created a much harder one.

People no longer struggle primarily with finding something to look at. They struggle with deciding what deserves to be believed. That distinction matters because attention and trust behave very differently. Attention can be purchased, engineered, and occasionally stolen. Trust is slower. It accumulates through consistency, judgment, competence and the uncomfortable requirement that what you say keeps matching what you actually do. A clever campaign might buy thirty seconds of somebody’s day, but no media budget can force that person to believe the person on the other side of it. In fact, the harder something appears to be trying to manufacture credibility, the more suspicious we’ve become of it.

You can see the consequences everywhere. Perfectly polished thought leadership that says almost nothing. Executives borrowing language from whatever management idea is fashionable that quarter. Websites filled with synthetic imagery of synthetic people doing synthetic work. Videos delivered with the cadence of someone who has spent more time studying how experts are supposed to sound than developing an opinion worth hearing. None of these things are necessarily dishonest. That’s almost what makes the problem interesting. They’re frequently the result of people trying so hard to appear credible that they accidentally remove all of the evidence that a real person is there.

The opportunity for leaders is therefore becoming strangely old-fashioned. Know something. Believe something. Be able to explain why. Admit where the edges of your knowledge are. Show up consistently enough that people can compare today’s claims with yesterday’s behavior. There will always be tricks for earning another click, another view or another moment in somebody’s feed. But in an environment overflowing with content, the leaders who matter won’t necessarily be the ones who become best at producing more of it. They’ll be the ones whose audience has learned that when they speak, there is probably something worth hearing.

Few people have watched that relationship between attention and credibility as closely as this Eggs! The Podcast guest, Dominic Forth. After more than two decades working across journalism, broadcasting, advertising and media strategy, Dominic has seen firsthand what makes an audience stop, what makes a message travel and, perhaps more importantly now, what makes people trust the person delivering it. Today, as CEO of Thought Leaders America, much of his work sits directly inside that increasingly valuable space between simply being visible and actually becoming believable.

From Newsrooms to Thought Leadership

Dominic Forth has spent more than two decades working at the intersection of media, messaging and audience behavior. He began his career training with the BBC, where he developed an early grounding in journalism, interview ethics and the mechanics of telling a story responsibly. After moving to the United States, his career took him through radio, local media, advertising, promotions and sales, giving him a close-up view of the decisions that determine which stories get attention—and which are quietly overlooked.

That experience eventually stretched across several very different markets, including Kansas City, Tampa, San Francisco, Oklahoma and Colorado. Along the way, Dominic worked with local businesses, advertisers and major media organizations, including Fox in San Francisco, where he saw firsthand how quickly audiences make judgments about what feels credible, relevant or worth watching. Focus-group research became a particular area of interest, showing him how seemingly small details—from presentation style to visual cues—could change the way a message was received.

Today, Dominic is the CEO of Thought Leaders America, where he works with entrepreneurs, executives, founders and experts who have something meaningful to say but often struggle to make that message visible. His work centers on helping them clarify their stories, sharpen their point of view, prepare for media appearances and build authority in a way that feels credible rather than manufactured. In a media environment where attention can be bought almost instantly, Dominic’s work is increasingly about the harder problem: making sure the audience believes the person who earned it.

Getting Attention Is Only the Beginning

Visibility can open the door, but what happens afterward determines whether anyone stays. Dominic’s experience across journalism, advertising and media training offers a useful look at what turns a moment of attention into something far more durable.

“Attention is almost cheap these days. You can buy attention pennies on the dollar with certain ad placements, but trust is priceless.”

Actionable insight: Treat attention as an invitation, not an accomplishment. A click, view or media appearance may introduce you to someone, but credibility is built through what they find once they start paying attention.

“If that’s fake, what else is fake?”

Actionable insight: Small signals matter more than most brands realize. Overproduced imagery, artificial environments or claims that feel inflated can create doubt well beyond the thing that triggered it. When trust is the goal, believable usually beats perfect.

“You have to start telling your story to get the feedback from other people of what’s interesting and what’s not interesting.”

Actionable insight: Don’t wait until your message feels finished. Put your ideas into conversations, presentations, interviews and writing, then pay attention to where people lean in. Strong points of view are often discovered in public before they’re polished in private.

“People try and ship the finished product. ‘I’ll speak when I’m ready because I’ve got to finish the story.’ But if you don’t get that feedback, then you’ll never get to the finished story.”

Actionable insight: Perfection can become a convenient form of hiding. The leaders who communicate well usually got there through repetition—saying the thing, hearing how it lands, tightening it and saying it again.

“You need to lead with your opinion first to hook people.”

Actionable insight: Expertise isn’t demonstrated by unloading everything you know. Start with the judgment your experience has earned you. Give people the conclusion worth paying attention to, then support it with the facts.

“What are the stakes?”

Actionable insight: Information becomes meaningful when people understand why it matters. Whether you’re pitching a client, leading a team or appearing on a podcast, make the consequence clear. Without stakes, even useful information can become background noise.

“It’s really the journey of being interviewed that is the most important, because it’s not until you’ve got a few reps in and you see the response, you get the questions, sometimes a question you’re not expecting—that’s where the coaching really starts to kick in.”

Actionable insight: Authority is developed under pressure, not merely prepared for beforehand. Put yourself in situations where people can question your thinking. The gaps you discover there are often more useful than another hour spent polishing the presentation.Make the Decision Before Time Makes It for You

The Long Game Is Belief

There’s no shortage of ways to get noticed anymore. The harder question is what happens after someone notices you. Do they believe you? Do they remember what you said? More importantly, does your track record give them a reason to come back the next time you speak?

That’s where the real work begins. Trust isn’t built in a launch, a campaign or a single great interview. It’s built in the accumulation of small moments where your words, judgment and actions continue to line up. That may be slower than chasing reach, but it also creates something far more durable than reach ever could.

The leaders and brands that stand out in the years ahead may not be the loudest or the most prolific. They’ll be the ones who become known for saying something worth hearing—and for proving, over time, that they mean it.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. The Speed of Trust — Stephen M.R. Covey
   A natural companion to this week’s central idea. Covey makes the business case that trust isn’t merely a soft cultural virtue; it has real economic consequences. When trust is high, organizations move faster and friction falls. When it disappears, nearly everything becomes harder and more expensive.

2. The Trusted Advisor — David H. Maister, Charles H. Green & Robert M. Galford
   Originally written with professional services in mind, but broadly useful for anyone whose business depends on clients believing their judgment. The book digs into the behaviors that separate someone who merely possesses expertise from someone people actually trust enough to follow.

3. Made to Stick — Chip Heath & Dan Heath
   Getting attention is one thing. Making an idea survive contact with an audience is another. The Heath brothers examine why certain messages are remembered, repeated and acted upon while others disappear almost immediately—a useful complement to Dominic’s discussion about sharpening ideas for media.

4. Storyworthy — Matthew Dicks
   One of the more practical books on discovering stories hiding inside ordinary experience. That connects directly with Dominic’s point that you often don’t fully understand your own story until you begin telling it, hearing the response and discovering which moments carry more meaning than you realized.

5. The Practice — Seth Godin
   Godin’s argument is less about waiting for confidence, inspiration or the perfect finished product and more about consistently putting meaningful work into the world. That fits nicely with Dominic’s advice to stop waiting until the story is finished and start getting the repetitions that ultimately make it better.

More to explore

Learn more about our featured guest — start here:

Thought Leaders America — https://www.thoughtleadersamerica.com/

Authority Brief — https://authoritybrief.com/

Dominic Forth on LinkedIn — https://www.linkedin.com/in/dominic-forth/

Thought Leaders America on LinkedIn — https://www.linkedin.com/company/thoughtleadersamerica/

Thought Leaders America on YouTube — https://www.youtube.com/@ThoughtLeadersAmerica

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

One of the more expensive mistakes you can make in business is also one of the easiest to defend: doing nothing.

It rarely feels reckless. Quite the opposite. Waiting often sounds responsible. We need a little more information. Let’s see how the quarter finishes. Let’s give the campaign another month. Maybe the employee turns it around. Maybe the market improves. Maybe the client comes back. Maybe the product finally catches. There’s always a perfectly reasonable argument for delaying a decision, particularly when making one means admitting that something isn’t working.

Entrepreneurs are especially susceptible to this because persistence is so deeply baked into the mythology of building a company. We celebrate the founder who heard “no” 100 times before finally getting a yes. We tell stories about businesses that survived years of struggle before breaking through. All of that has some truth in it. But perseverance and indecision aren’t the same thing, and the distinction gets harder to see when you’ve already invested time, money, reputation, or some portion of your identity into the outcome.

In my own businesses, I’ve been guilty of this. I’ve certainly kept things going longer than I should have. Ideas. Services. Clients. Strategies. Sometimes because I believed there was still something there, sometimes because changing direction created another pile of work I didn’t particularly want, and sometimes because abandoning something made the effort already spent feel wasted. The irony, of course, is that none of those reasons changes what happens next. Yesterday’s investment is gone either way. The only decision available is what deserves tomorrow’s.

That’s where the cost of waiting becomes easy to underestimate. Businesses tend to account for money that leaves the bank. They’re considerably worse at accounting for opportunity. The employee you tolerate occupies a seat someone better could fill. The mediocre service you continue supporting consumes resources that could strengthen the profitable one. The six months spent debating a hire, acquisition, new market, or technology initiative don’t show up neatly on the P&L as an “indecision expense.” But the expense is there. Competitors move. Markets change. Compounding happens for somebody else.

Good leadership doesn’t require perfect decisions; there aren’t enough perfect decisions available to run a company that way. It requires developing enough judgment to recognize when more information will materially improve the decision and when “more information” has simply become cover for avoiding it. Sometimes the better choice really is to wait. Sometimes the correct answer is no. The problem begins when we pretend that choosing neither has somehow preserved our options. Time has already made a choice for us.

That idea sits at the heart of something Eggs! The Podcast guest Mike Milligan calls the “paralysis penalty.” Milligan, founder of One Oak Financial, uses the concept in the context of money: capital left sitting idle while someone waits indefinitely for certainty can quietly sacrifice years of potential growth. But his argument extends well beyond an investment account. For anyone responsible for allocating money, people, attention, or time, indecision isn’t neutral. It has a return too—and sometimes it’s a terrible one.

When Financial Planning Stops Being Generic

Mike Milligan has spent nearly three decades in financial planning, but his approach was shaped long before he entered the industry. As a kid, he watched his grandmother, Elizabeth, rebuild her life after the death of his grandfather by selling collard sandwiches at construction sites, convenience stores, and fairs. Milligan went along for the ride—learning how to sell, count money, keep track of cash, and, perhaps more importantly, how much ingenuity can come from necessity. He describes his grandmother as someone who “innovated out of desperation,” an early lesson that would later influence the way he thought about entrepreneurship, money, and conventional wisdom.

After college, Milligan entered the traditional wealth-management world, working inside large financial institutions where he quickly became uncomfortable with the industry’s priorities. He recalls Monday meetings centered on revenue targets, loan volume, investment accounts, and insurance policies without much discussion of the actual people behind those numbers. Eventually, that experience pushed him in another direction. In 2012, he went independent and founded what became One Oak Financial, building a firm around the idea that financial planning should begin with the life a client is trying to create rather than a standardized collection of products and benchmarks.

Today, Milligan leads One Oak Financial, writes books, hosts a podcast and radio show, teaches at the university level, and works extensively with entrepreneurs on tax and financial strategy. His books include The One of a Kind Financial Plan and Retirement Déjà Vu, where he develops the idea of the “paralysis penalty”—the very real cost that can accumulate when uncertainty keeps someone from acting. It’s a financial concept on its face, but as our conversation made clear, it has plenty to say about how leaders make decisions everywhere else, too.

The Cost of Waiting for Certainty

Milligan’s “paralysis penalty” starts with money, but the principle applies just as easily to hiring, strategy, product decisions, and the hundred other places leaders can get stuck waiting for perfect information. The goal isn’t to become reckless. It’s to recognize when caution has stopped protecting you and started costing you.

“If you don’t do anything, you’re actually losing at the end of the day.”

Actionable insight: Start treating inaction as one of the options on the table—and evaluate its cost accordingly. A delayed decision consumes time, capital, attention, and opportunity just as surely as a bad decision can.

“At some point you’ve got to take a little bit of a risk… I’ve gotten enough information. I’ve asked enough questions.”

Actionable insight: There’s a point where another meeting, another spreadsheet, or another week of research stops improving the decision. Define what “enough information” looks like before you begin, then make the call when you get there.

“The most powerful question you can ask to see if something is legit or not legit is: why? And then you ask why again, and then you ask why again.”

Actionable insight: When uncertainty is holding up a decision, interrogate the assumptions underneath it. Repeatedly asking why forces vague concerns to become specific—and specific problems are considerably easier to solve.

“Entrepreneurs hold on to ideas that are not revenue producing too long, saying, ‘I’m just gonna give it a little bit more of an opportunity.’”

Actionable insight: Persistence needs a deadline. Establish the evidence an idea has to produce—and by when—before enthusiasm and sunk costs make abandoning it unnecessarily difficult.

“It’s better to sometimes cut losses than it is to keep going down that same path.”

Actionable insight: What you’ve already spent is gone. The useful question is whether you would invest the next dollar, week, or year knowing what you know today. If the answer is no, history isn’t a good enough reason to keep going.

“If you’re waiting, you’re losing to the process.”

Actionable insight: Waiting for conditions to become perfect usually means someone else gets to operate while you observe. Markets move, competitors learn, employees develop, and opportunities compound. The cost of being late is often invisible until it’s permanent.

“If you don’t have control of your calendar, you really don’t own a business. You just own a job.”

Actionable insight: Indecision can become operational, too. If every important choice still has to pass through the founder, the organization eventually moves at the founder’s speed. Building leaders who can make good decisions without you isn’t just delegation—it’s how the company gets its velocity back.

Make the Decision Before Time Makes It for You

There’s a version of patience that is disciplined, and there’s a version that is just fear dressed up as prudence. The trouble is they often look exactly the same from the inside. Both involve waiting. Both can be defended with data. Both can sound reasonable in a meeting. The difference is whether the delay is buying you something useful or simply postponing the discomfort of choosing.

That’s the part of the paralysis penalty that matters most to leaders. Every meaningful decision carries some uncertainty. There is no clean moment when the market becomes obvious, the hire becomes risk-free, the strategy becomes guaranteed, or the numbers remove every possible objection. Leadership is partly the work of deciding anyway—after enough diligence, with enough conviction, and with enough humility to change course if the evidence changes.

The aim isn’t speed for its own sake. It’s movement with intent. Make the decision, measure what happens, and stay willing to adjust. Because while a wrong move can cost you, standing still has a price too. And in business, that price is usually paid quietly, over time, in opportunities you never get back.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Thinking in Bets — Annie Duke
   Most consequential decisions have to be made before all the facts are available. Drawing on her experience as a professional poker player, Duke makes a useful distinction between the quality of a decision and the outcome it happens to produce. A great antidote to the idea that good leadership means waiting until you can be certain.

2. Quit: The Power of Knowing When to Walk Away — Annie Duke
   Persistence gets most of the good press, but knowing when to stop can be just as valuable. Duke examines sunk costs, escalation of commitment, status quo bias, and the other forces that keep smart people pouring resources into things that no longer make sense. It pairs particularly well with Mike’s warning that entrepreneurs routinely hold onto non-producing ideas for too long.

3. The One of a Kind Financial Plan — Mike Milligan
   The philosophy behind much of this week’s conversation. Milligan pushes against one-size-fits-all financial advice and argues that a plan should begin with what someone is actually trying to accomplish, rather than a predetermined collection of products or benchmarks. The financial application is specific, but the larger lesson—question conventional wisdom and make intentional choices—is useful well beyond money.

More to explore

Learn more about our featured guest — start here:

Mike Milligan — More from Mike, including his writing, financial education, speaking, and planning work. MikeMilligan.com

Ideas by Mike™ — Mike’s podcast exploring financial planning, money, purpose, and the thinking behind his one-of-a-kind approach. Listen to Ideas by Mike™

1 OAK Financial — The financial planning firm founded by Mike and the home of his individualized planning approach. Explore 1 OAK Financial

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

There’s a particular kind of confidence that comes from owning a profitable business. Payroll clears. Customers keep coming back. There’s money left over at the end of the month. After years of grinding, those numbers become proof that the thing works. And they are proof—just not necessarily proof of what most owners think they are.

That said, a profitable company and a valuable company aren’t the same thing. You can build an exceptional income stream for yourself while simultaneously building something another person would have very little interest in owning. If every important customer relationship belongs to you, every major decision runs through you, the team depends on knowledge that lives mostly in your head, and revenue disappears the moment you stop pushing the machine forward, you may have created a great job. Maybe even a very lucrative one. But you haven’t necessarily created an asset.

That distinction matters long before anybody starts talking about selling. In fact, I’d argue that saleability is one of the more useful tests of business quality even if you have no intention of going anywhere. Strip away the language of M&A and what a buyer is really asking is pretty straightforward: What happens to this company if the founder gets hit by a bus, takes six months off, loses a major client, or simply stops being the person holding everything together? The more uncomfortable the answers, the more fragile the business probably is.

Founders don’t always see that fragility because we’re standing inside it. We know how the customers think, which employee can actually solve a problem and which one just looks busy, and which numbers in the forecast are real and which ones require a little optimism. But over enough years, that accumulated instinct becomes part of the way we do business. It feels like an advantage — and while we’re there, it is. The problem comes later when “the way we get things done” can’t be transferred with the company.

Buyers look at the same business from the other side of the table. They’re looking for recurring revenue instead of constant reinvention, a capable management team instead of a heroic owner, and a healthy spread of customers instead of one giant account that could leave next quarter. Clean financials, repeatable processes, institutional knowledge that exists somewhere other than somebody’s memory. They aren’t just buying earnings. They’re trying to understand how likely those earnings are to survive once the keys change hands.

That may be the more useful way for entrepreneurs to think about enterprise value in the first place. Building a more valuable company isn’t primarily about making it look attractive for some hypothetical buyer. It’s about reducing the number of ways the business can break. If you strengthen the team, diversify the revenue, clean up the financial story, document what matters, and make yourself less essential to everyday operations, you haven’t merely prepared for an exit. You’ve built a company that gives you more options while you still own it.

Few people see that distinction as clearly as Eggs! The Podcast guest Holli Moeini, author of Finding the Missing Millions in M&A. After 35 years as a CPA and decades spent growing, buying, selling, and advising businesses, Holli has seen what owners believe makes a company valuable—and what buyers actually pay for. The gap between those two ideas can be worth millions.

From the Numbers to the Deal Table

Holli Moeini has spent more than three decades inside the financial machinery of businesses—first as a CPA, then as an operator, buyer, seller, and advisor. Her career began in public accounting and audit, but an early role inside a company preparing for a sale pulled her into M&A almost by accident. From there, she moved deeper into corporate leadership, helping grow and scale companies and using acquisitions as a tool to accelerate that growth. Importantly, Holli notes that her M&A education didn’t come from traditional accounting training; she learned the work directly from an investment banker serving on her board and then refined that knowledge deal by deal.

After leaving corporate life following the pandemic, Holli found herself at an unexpected crossroads. A conversation with longtime M&A executive Adam Coffey—who has participated in billions of dollars in exits—helped push her toward entrepreneurship and eventually into advising owners navigating the same decisions she had spent years making from inside companies. What she found in the small- and middle-market business world was a widening gap between increasingly sophisticated buyers and owners who often had little guidance on how to prepare for a transaction.

That gap became the foundation for Holli’s work today and for her book, Finding the Missing Millions in M&A. Through her advisory work, writing, and education, she focuses on helping business owners understand the financial and operational decisions that create—or quietly destroy—enterprise value long before a company ever reaches the negotiating table.

Where Value Actually Comes From

Once you stop treating profitability as a proxy for value, the business starts to look different. Holli’s advice offers a useful way to examine the company through the eyes of the person who may someday have to own it without you.

“My philosophy is that you should always be ready to sell. The beauty of always being ready to exit is that you’re creating more value for you and your family right now.”

Actionable insight: Don’t wait for an acquisition offer to expose weaknesses you could have fixed years earlier. Build the company as though someone might inspect it tomorrow; even if you never sell, the result should be a cleaner, stronger, more resilient business.

“When you make my risk increase as a buyer, your price goes down. That’s how that works.”

Actionable insight: This may be the simplest way to think about enterprise value. Look at the business and identify what would make a stranger nervous about owning it—then start removing those risks one by one.

“I de-risk the buyer by having a leadership bench or a second in command that can replace me. That makes my value go up.”

Actionable insight: Founder dependence might feel like importance while you’re running the company, but it becomes a liability when someone wants to buy it. Start deliberately moving decisions, relationships, and institutional knowledge beyond yourself.

“Gross profit needs to be above 30%. Your selling, general and administrative expense needs to be less than 20%. And then your net income needs to be above 10%.”

Actionable insight: Holli uses Adam Coffey’s 30-20-10 rule as a diagnostic, not simply a scoreboard. If one of those numbers is off, don’t just push harder for revenue; figure out whether the underlying issue is pricing, cost of delivery, overhead, or something else entirely.

“If you have all of your revenue in a few companies’ baskets, my risk goes up as a buyer. And recurring revenue is a big deal here as well.”

Actionable insight: A $5 million business with one customer responsible for half its revenue is a very different asset from a $5 million business with a diversified customer base and predictable contracts. Growth matters, but the composition and durability of that growth matter too.

“Whatever you have in your business that’s risky is not attractive to buyers, period. So any way you can de-risk that is good and makes you more valuable.”

Actionable insight: Conduct a risk audit the same way a buyer would. Customer concentration, undocumented processes, shaky financials, dependence on one employee, inconsistent margins, owner-controlled relationships—every one of them gives the buyer a reason to discount what you’ve built.

“Your emotional and blood, sweat, and tears and everything that went into it—that is not transferable. You have to put in the time to prepare. I’d say, please prepare three years before.”

Actionable insight: Twenty years of sacrifice may explain why a business matters to its founder, but buyers can’t put that history on a balance sheet. If an exit is even a possibility, give yourself enough runway to turn personal effort into systems, financial performance, leadership depth, and assets someone else can actually own.

Build the Business Someone Else Could Run

The useful thing about looking at your company through a buyer’s eyes is that you don’t actually need a buyer for the exercise to pay off. If the business depends too heavily on you, if too much revenue comes from too few customers, if the financials are hard to explain, or if the processes only work because a handful of people know how to hold them together, those are problems whether you plan to sell next year, ten years from now, or never. A buyer may be the one who eventually puts a price on those weaknesses, but you’re already living with the risk.

That’s what makes this conversation bigger than M&A. The goal isn’t to spend every day polishing the company for some imaginary transaction. It’s to build something durable enough that your options expand over time rather than narrow. A business that can operate without constant intervention is easier to grow, easier to hand down, easier to step away from, and, yes, considerably easier to sell.

Profitability is still important. It just isn’t the finish line. The better question is what remains when the founder steps out of the picture. If the answer is a capable team, predictable revenue, clean numbers, good systems, and a company that knows how to keep moving, then you’ve built something considerably more valuable than a paycheck.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Finding the Missing Millions in M&A — Holli Moeini
   The natural place to continue this week’s conversation. Holli looks at the moments where value is quietly created or lost during a transaction—from the financial story and working capital to diligence, earnouts, and integration. More importantly, it reinforces the idea at the center of this week’s issue: maximizing the value of a business starts well before there’s a buyer at the table.

2. Built to Sell — John Warrillow
   One of the clearest books on the difference between owning a business and owning a business that can function without you. Warrillow’s central argument maps almost perfectly to this week’s theme: if the company depends on the founder for sales, decisions, relationships, and delivery, that dependence eventually becomes a ceiling on value.

3. The Exit-Strategy Playbook — Adam Coffey
   Coffey takes the owner through the sale process from the perspective of someone who has spent decades on the private-equity side of the table. It’s particularly useful for understanding how buyers evaluate risk, why preparing years ahead matters, and how the decisions made while you’re still operating the company eventually show up in the price someone is willing to pay.

More to explore

Learn more about our featured guest — start here:

• Holli Moeini’s website

• Holli on Linkedin

• Behind the Numbers

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

There is a strange bargain buried inside ambition. The better you get at something, the more people begin to know you for it. Over time, that recognition hardens into identity. You are no longer someone who runs a company; you are a founder. You are no longer someone who makes things; you are a creative. You are no longer someone who sells, leads, advises, builds, or manages. The work stops being something you do and starts becoming shorthand for who you are.

For entrepreneurs, that transition can happen almost invisibly. Building a business asks so much of you that it is easy to give more than just your time. You hand over your attention, your relationships, your confidence, your sense of progress. Eventually, the company’s wins feel like your wins and its losses feel strangely personal. Revenue is no longer just revenue. A big client validates you. A bad quarter indicts you. Someone praises the business, and you feel taller; someone dismisses it, and you carry the criticism around longer than you probably should. The boundary between person and profession gets thinner until, for some people, it disappears altogether.

That arrangement can work for a very long time. In fact, success tends to reinforce it. The more closely your identity is tied to what you are building, the easier it is to justify the long hours, the sacrifices, and the obsessive attention to detail. There is real power in that kind of commitment. There is also risk. Businesses get acquired. Partnerships end. Industries change. Clients leave. Careers that once felt permanent become obsolete. Sometimes the company survives and you simply stop loving the work. The uncomfortable question arrives either way: if this is no longer mine, what exactly is left of me?

Athletes encounter that question earlier and more dramatically than most of us. Their careers have a visible ending. One day there is a uniform, a schedule, a team, a scoreboard and a role everyone understands. Then, sometimes by choice and sometimes without warning, all of it is gone. Eggs! The Podcast guest and founder of Athlete 5, Eric Dahl, described the transition as a “first death.” That language sounds severe until you consider what has actually been lost. The athlete has not simply lost a job. They may have lost the organizing principle around which their entire adult life was built.

Entrepreneurs are not so different. We simply tend to get more warning, and often ignore it. The company name is in the bio. The work follows us home. Our closest relationships are tangled up with the business. We introduce ourselves by title and measure years by launches, deals, clients and milestones. None of that is inherently unhealthy. Work can be meaningful. Building something can be one of the most satisfying things a person does. The problem begins when achievement becomes evidence of worth, because eventually every scoreboard changes.

The more useful question, then, is not whether we should care less about the work. It is whether we have built enough of a life outside of it to survive the moment when the work changes. Eric’s argument is that the game can end without the person ending with it. The discipline, judgment, resilience, relationships and experience remain after the jersey comes off. That is as true for someone leaving a locker room as it is for someone leaving a boardroom.

That is the territory Eric has been exploring through Athlete 5 and his book, Winning the Post Game. His work is centered on athletes facing the uncomfortable transition from being known for what they did to deciding who they will become next. But the premise travels well beyond sports. Every ambitious person eventually reaches a point where the scoreboard they have been watching no longer tells the whole story. The challenge is making sure we know who we are before that day arrives.

The Game Ends. The Person Doesn’t.

Eric Dahl’s career has never followed a particularly straight line. A Salt Lake City native, he began in real estate development and investment, building his career during the rapid growth of the early 2000s before the 2008 financial crisis forced a hard reset. That experience pushed him into marketing, where he went on to lead agencies, work as a fractional CMO and consultant, and support brands including State Farm, the WNBA, and Better Homes and Gardens.

Sports, however, was the thread that never really disappeared. A lifelong athlete and sports enthusiast, Eric stayed close to competition even when his professional life went elsewhere, including a stint working with the Utah State Athletic Commission at MMA events. Over time, that interest converged with his experience in business, marketing, leadership, and career transition, eventually becoming Athlete 5, a company focused on helping athletes navigate the years after competition ends.

His new book, Winning the Post Game: The Game Ends. You Do Not., extends that work beyond career placement alone. Eric focuses on helping athletes rebuild a sense of direction around purpose, mental and physical health, relationships, and personal identity—areas that can become surprisingly difficult to navigate once the structure and certainty of sport disappear. It is a framework built for athletes, but the underlying question is much broader: what happens when the role that once explained who you were no longer exists?

What Survives the Scoreboard

Once the title, uniform, or company name falls away, what remains is usually more valuable than we give it credit for. Eric’s perspective on life after sports offers a useful framework for anyone trying to separate the skills they’ve built from the role that once gave those skills a name.

“It feels like a first death for them…they don’t know who they are beyond the playing field.”

Actionable insight: ay attention to how you describe yourself when someone asks what you do. If the answer is entirely a title, company, or profession, it may be worth spending some time identifying what actually survives if that role disappears.

“The game was wonderful, but I’m still important outside of my jersey.”

Actionable insight: There is nothing wrong with loving the work or taking pride in what you’ve built. Just don’t let its success become the sole evidence of your own value. Companies, careers, and markets change; the person who built something worthwhile is still there when they do.

“The traits and the unique characteristics that you have that have made you successful on the playing field are going to transfer nicely if you allow for them.”

Actionable insight: When a chapter ends, resist the urge to think you are starting from zero. The context may be new, but discipline, judgment, resilience, leadership, creativity, and the ability to perform under pressure all travel remarkably well.

“What that really boils down to is who are you surrounding yourself with?”

Actionable insight: Transitions tend to expose the quality of our relationships. Build a network before you desperately need one, and make sure it includes people who know you beyond the role you currently occupy.

“If I went in with a mentality that I was there to provide value to others and not to try to make it about me, that’s where things really took flight.”

Actionable insight: The best networking rarely feels like networking. Become useful to good people without keeping a running ledger of what you expect back. Careers are long, and relationships have a funny way of becoming valuable years after the original interaction has been forgotten.

“So oftentimes it’s like, ‘I want to be like this person or that person.’ No, no, no—just be yourself.”

Actionable insight: Reinvention does not require manufacturing a new personality. A better starting point is understanding which parts of your existing experience are genuinely yours, then finding a new place for them to matter.

“I focus on this idea of replacing the scoreboard with a report card.”

Actionable insight: Business gives us plenty of scoreboards—revenue, valuation, headcount, clients, followers, awards. Keep them, but add a report card that measures the parts of life those numbers cannot: health, relationships, purpose, curiosity, and whether the work is still producing a life you actually want.

The Parts That Stay With You

There is a temptation, especially among ambitious people, to treat reinvention as starting over. I don’t think that’s quite right. A company can disappear. A title can change. A career can end. But the years spent learning how to make decisions, solve problems, lead people, recover from mistakes, build relationships, and keep moving when things get difficult don’t vanish with the old role. Those things are not attached to the business card. They belong to the person.

Maybe that is the more useful way to think about identity in the first place. The goal isn’t to care less about the work or to keep some careful emotional distance from everything we build. I’m not sure great work happens that way. It is simply to remember that our careers are chapters, even when we are deep enough inside one that it feels like the whole book. Eric’s athletes are forced to confront that reality earlier than most of us. Entrepreneurs eventually get there too.

There will always be another scoreboard. Another company, another project, another season, another definition of success. The trick is making sure the person keeping score remains bigger than any one of them.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Winning the Post Game: The Game Ends. You Do Not. — Eric Dahl
   The natural starting point this week. Dahl wrote Winning the Post Game for athletes confronting life after competition, but its central idea applies just as readily to founders and business leaders: when a defining chapter ends, the skills, relationships, discipline, and experience developed along the way don’t disappear with it.

2. Working Identity: Unconventional Strategies for Reinventing Your Career — Herminia Ibarra
   One of the better books on what career reinvention actually looks like in practice. Ibarra pushes against the idea that we need to completely understand our “next thing” before making a move, arguing instead that new identities are often discovered through experimentation, new relationships, and trying on different versions of what comes next.

3. The Second Mountain — David Brooks
   Brooks examines the difference between a life built around achievement and one increasingly organized around commitment, relationships, vocation, and meaning. It pairs particularly well with this week’s question because it asks what happens after the traditional markers of success stop being enough.

4. Designing Your Life — Bill Burnett and Dave Evans
   Built from the design-thinking work of two Stanford educators, Designing Your Life offers a practical way to think about transitions without pretending there is one perfect career waiting to be discovered. Instead, Burnett and Evans approach a meaningful life as something that can be tested, adjusted, and deliberately built over time.

More to explore

If you’d like to dive deeper into Eric Dahl’s work, here are a couple great places to start:

• Athlete 5

• Eric Dahl on LinkedIn

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

For the better part of two decades, marketing has been a race toward efficiency. We built automation to send more emails, software to publish more content, and algorithms to optimize every click, impression, and conversion. Somewhere along the way, “more” quietly became the objective. More posts. More ads. More content. More noise.

Then artificial intelligence arrived, and everyone assumed the rules had changed.

If AI could write articles, generate videos, design graphics, and answer questions in seconds, surely the old playbook was dead. Why invest in relationships when algorithms could manufacture attention? Why earn credibility when you could simply produce more content?

But that’s the funny thing about real paradigm shifts. They rarely eliminate the fundamentals. They expose them.

As AI floods the internet with an endless supply of competent-but-forgettable content, the oldest principles in marketing are becoming the most valuable again. Trust. Reputation. Expertise. Authenticity. Large language models don’t simply reward whoever publishes the most. They increasingly lean on trusted sources, recognized experts, reputable publications, and established credibility to determine which answers deserve to be surfaced. In a world where content has become abundant, trust has become scarce.

That shift has quietly turned one of marketing’s oldest disciplines into one of its newest competitive advantages. Public relations—long dismissed by many as difficult to measure or little more than a branding exercise—is suddenly becoming foundational. Earning credible media coverage, building authentic thought leadership, and becoming a trusted voice aren’t just good for your reputation anymore. They may determine whether AI recommends your business at all.

I sat down with Eggs! The Podcast guest Jackson Wightman, founder of Proper Propaganda and author of The Tech PR Playbook, to explore this unexpected reversal. Our conversation wasn’t really about PR or AI optimization. It was about a lesson business seems destined to relearn every few decades: technologies come and go, platforms rise and fall, but companies built on genuine credibility almost always find a way to win.

Why AI Is Rewarding the Most Human Companies

Jackson Wightman is the founder of Proper Propaganda, a technology-focused public relations agency that has spent the past 15 years helping innovative companies shape their public narrative. A veteran communications strategist with roots in political campaigns, Jackson now sits at the intersection of traditional PR and one of marketing’s fastest-evolving disciplines: Generative Engine Optimization (GEO).

As AI-powered search reshapes how buyers discover companies, Jackson has been studying a surprising trend. Rather than replacing public relations, large language models are increasing the value of earned media, authentic thought leadership, and trusted third-party credibility. His work challenges many of the assumptions businesses have made about AI marketing and offers a practical framework for earning visibility in an increasingly AI-driven world.

In this conversation, we explore why PR is experiencing an unexpected renaissance, how companies should think about optimizing for AI, why trust is becoming the scarcest commodity on the internet, and what founders can do today to ensure both humans—and AI—find them worth listening to.

Trust Is the (Old) New SEO

If the introduction argued that AI is rewarding timeless fundamentals, this conversation explains why. Jackson has spent the last 18 months watching AI search evolve from the front lines, and what he's seeing challenges much of the conventional wisdom around marketing, PR, and discoverability.

“Twenty-seven percent of AI answers in aggregate pull from journalistic sources.”

Actionable insight: For years, marketers viewed PR as a "nice-to-have" while performance marketing consumed the budget. AI is quietly flipping that equation. If large language models increasingly rely on trusted, third-party publications to inform their answers, then earned media isn't just building awareness anymore—it's becoming part of your discoverability strategy. If your company has been ignoring PR, now is the time to reconsider.

“Instead of these campaigns that are kind of carpet bombing runs... three or four of the right outlets will do a lot.”

Actionable insight: Success is becoming less about volume and more about precision. Rather than chasing every podcast, publication, or guest article that will have you, identify the handful of outlets your customers actually trust. A single placement in the right publication may carry more long-term value than dozens of mediocre mentions.

“Most of us can now tell when content is made with AI.”

Actionable insight: The opportunity isn't simply avoiding AI-generated content. It's creating something AI can't easily imitate: original experiences, unique perspectives, and authentic expertise. As generic content floods the internet, businesses with a recognizable human voice aren't just avoiding penalties—they're becoming easier for both people and AI to recognize as credible.

“You need to know what LLMs your customers are using. If I optimize for Claude and your customers are on ChatGPT, we've literally flushed your money down the toilet.”

Actionable insight: "AI optimization" isn't one thing. Different audiences use different platforms, and those platforms often produce very different answers. Before investing in GEO, ask your customers which AI tools they actually use—and how they use them. A little customer research can save a lot of wasted effort.

“ChatGPT and Claude cite the same content... only 8% of the time.”

Actionable insight: That statistic surprised me. We tend to talk about "AI" as if it's one giant ecosystem, but each model has its own sources, priorities, and behaviors. The lesson isn't that you need to optimize for every platform—it's that broad assumptions are becoming less valuable than real data about your own customers and your own market.

“Asking your customers what LLMs they use and how they use them... if you don't, you are running blind.”

Actionable insight: Perhaps the biggest takeaway from our conversation was also the simplest. Before hiring an agency, rewriting your website, or chasing the latest AI tactic, spend an afternoon talking to your customers. Understanding how they're searching, researching, and making decisions will almost always outperform chasing the latest marketing trend. In an era obsessed with artificial intelligence, genuine human insight may still be your greatest competitive advantage.

…the More They Stay the Same

Every major technological revolution creates winners and losers. Not because the technology itself decides, but because it exposes what was valuable all along.

The internet rewarded those who could publish. Social media rewarded those who could capture attention. AI appears to be rewarding something much older: credibility. That should be encouraging. Because unlike algorithms, trust can’t be automated, outsourced, or generated with a prompt. It still has to be earned.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch the interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. The Tech PR Playbook — Jackson Wightman
   A practical guide to modern public relations in the age of AI. Jackson expands on many of the ideas we discussed—from earned media to Generative Engine Optimization (GEO)—and provides a framework for increasing your brand’s visibility in AI-driven search.

2. Trust Me, I’m Lying — Ryan Holiday
   An insider’s look at how media narratives are created and manipulated. While written well before the AI era, it’s a valuable reminder that understanding the mechanics of media is just as important as understanding the technology that distributes it.

3. The Long Game — Dorie Clark
   One of the best books on building long-term reputation instead of chasing short-term attention. As AI increasingly rewards credible, established voices, Dorie’s argument feels more relevant than ever.

4. The Reputation Economy — Michael Fertik & David C. Thompson
   A thoughtful examination of how reputation has become a measurable business asset. Published years before ChatGPT, its central thesis—that trust is an increasingly valuable currency—has only become more true.

5. The Almanack of Naval Ravikant — Eric Jorgenson
   A reminder that enduring leverage doesn’t come from working harder—it comes from building unique knowledge, a recognizable perspective, and a reputation that compounds over time. In an era of infinite AI-generated content, those qualities may become even more valuable.

More to explore

If you’d like to dive deeper into Jackson Wightman’s work, here are a few great places to start:

• Proper Propaganda - Jackson Wightman’s PR Agency

• Jackson Wightman on LinkedIn

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

A few years ago, simply saying your company used AI was enough to turn heads. Investors paid attention. Customers leaned in. Entire businesses seemed to appear overnight simply because they had found a way to attach those two letters to their product. Today, that advantage is disappearing.

We’ve joked about it more than once on Eggs!. There was a period where it seemed like every software company woke up and decided they needed an AI feature. AI chat. AI search. AI writing. AI summaries. Sometimes those features solved legitimate problems. Other times, it felt more like a race to make sure nobody’s product looked behind the times. I don’t think we’re in that moment anymore.

Lately, I’ve found myself asking a different question. Between ChatGPT, Claude, Cursor, ClickUp Brain, and a growing list of AI-powered tools, I’ve accumulated more subscriptions than I’d care to admit. Some of them have become indispensable. Others I’m constantly reevaluating. Every company wants another ten or twenty dollars a month because they’ve added AI, and eventually you stop asking whether a product has AI and start asking whether it’s actually worth paying for.

That feels like an important shift—not because AI suddenly matters less, but because it’s becoming expected. Nobody advertises power steering anymore. Nobody markets cloud computing as though it’s revolutionary. Those technologies didn’t lose their value; they simply became part of the foundation. Once that happened, the conversation naturally shifted from the technology itself to what it enabled people to accomplish. It seems to me that AI is arriving at that same point.

What’s interesting is where that leaves the rest of us.

For all the attention AI has received, I wonder if it’s quietly pushing us back toward fundamentals that never stopped mattering in the first place. The easier it becomes to generate content, automate workflows, and remove friction, the more valuable uniquely human qualities begin to feel. Judgment. Creativity. Trust. Curiosity. Real relationships. Those things haven’t become more important because AI exists—they’ve become more noticeable because everything else is becoming easier to replicate.

That’s why this week’s conversation with Eggs! The Podcast guest, entrepreneur and PyCube founder, Sam Yeruva, resonated with me. Every time the discussion drifted toward AI, he pulled it back to the customer, the workflow, or the problem that actually needed solving. It wasn’t a rejection of technology. It was a reminder that technology has always been a means to an end. The companies that endure aren’t the ones with the newest tools. They’re the ones that understand people well enough to solve problems worth solving.

Maybe that’s the biggest lesson of this AI era. The future isn’t asking us to abandon the fundamentals in favor of something new. If anything, it’s reminding us that the fundamentals were the point all along.

Building for What Doesn’t Change

Sam Yeruva has spent much of his career at the intersection of emerging technology and practical business problems. An engineer by training, he launched his first company in his early twenties before growing and ultimately selling it to Bain Capital. His second venture focused on blockchain and smart contracts—well before those technologies became mainstream—and was acquired before the product had even fully reached the market. Today, as founder and CEO of PyCube, he’s applying those same instincts to one of the most complex industries in the world: healthcare.

What makes Yeruva interesting isn’t simply that he’s been early to multiple technology waves. It’s that he no longer starts with technology at all. Years spent working alongside hospitals exposed him to a different reality. Behind world-class physicians and cutting-edge medicine, he found organizations buried under operational complexity—critical tissue samples delayed or misplaced, inventory systems that couldn’t account for what they owned, and staff too overwhelmed to step back and improve the systems they relied on every day. Rather than asking where AI or automation might fit, he began asking a simpler question: Where is the friction? Then he built technology around the answer.

That philosophy runs through every part of this conversation. Instead of chasing whatever technology happens to be making headlines, Yeruva argues that lasting companies are built by solving problems that persist long after the headlines fade. It’s a perspective shaped by experience rather than theory—and one that feels especially relevant as AI moves from novelty to necessity.

The Difference Between Technology and Progress

The best conversations don't just offer answers—they give you a different way to think. Throughout our discussion, Sam repeatedly reframed ideas that many entrepreneurs take for granted, replacing popular assumptions with principles that have guided three successful companies. Here are a few that stood out.

“Technology doesn't sell… it's the use cases. What are you using it for? Are we solving real problems?”

Actionable insight: Before adding another feature, ask yourself a harder question: What customer problem becomes easier because this exists? If the answer isn't immediately obvious, the feature probably isn't your competitive advantage.

“Follow the problems and apply technology where it's needed. Don't do it around.”

Actionable insight: Great businesses rarely begin with a technology. They begin with friction. Spend more time observing where customers lose time, money, or momentum, and the right solution becomes much easier to identify.

“Improving your product doesn't mean it's going to improve adoption. Improving adoption automatically improves your product.”

Actionable insight: Entrepreneurs often hide inside product development because it feels productive. Real progress usually starts when customers begin using what you've already built. Every conversation with a paying customer teaches you more than another month spent adding features.

“Seeing is believing.”

Actionable insight: If you're introducing something genuinely new, don't expect people to imagine its value. Show them. Whether it's a prototype, a live demo, or a simple proof of concept, reducing uncertainty is often more persuasive than improving your pitch.

“AI should be the cherry on the top rather than actually the product itself.”

Actionable insight: AI is rapidly becoming table stakes. The companies that stand out over the next few years won't be the ones talking the most about AI—they'll be the ones quietly using it to deliver a noticeably better outcome.

“When AI is moving this fast… look for the statics.”

Actionable insight: Markets change. Customer needs endure. Instead of anchoring your business to whatever technology is evolving fastest, anchor it to problems that aren't going away. Let technology strengthen your foundation—not become the foundation itself.

The Tools Will Change. The Principles Won't.

Every generation convinces itself that the latest technology changes the rules. Sometimes it does. More often, it changes the speed of the game while leaving the fundamentals exactly where they were. Businesses still win by solving meaningful problems. Leaders still succeed by earning trust. Customers still reward companies that make their lives easier. AI may transform how we build, communicate, and operate, but it doesn’t replace the timeless work of understanding people.

That’s what I appreciated most about this conversation with Sam. Rather than getting caught up in predictions about where AI is headed next, he kept bringing the discussion back to what isn’t changing. Curiosity. Empathy. Execution. The willingness to spend time with customers before writing code. The discipline to solve yesterday’s problems with tomorrow’s tools instead of the other way around. Those are advantages that don’t disappear when the next model is released, or the next buzzword takes over.

As AI becomes more accessible—and eventually more invisible—the companies that stand out won’t necessarily have better technology. They’ll have better judgment. They’ll ask better questions, identify better opportunities, and remain relentlessly focused on outcomes instead of features. That’s a refreshing reminder in an industry obsessed with what’s new: the future still belongs to the people who solve real problems for real people.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch Sam’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. The Mom Test by Rob Fitzpatrick — If Sam’s biggest lesson is to solve problems before building technology, The Mom Test is required reading. It teaches you how to have customer conversations that uncover real pain points instead of polite encouragement—helping you validate ideas before investing months building the wrong solution.

2. Competing Against Luck by Clayton Christensen — Christensen’s “Jobs to Be Done” framework perfectly complements Sam’s philosophy. Customers don’t buy products because they’re innovative; they “hire” them to solve a problem. Once you understand the job, the technology becomes secondary.

3. Obviously Awesome by April Dunford — One of the biggest takeaways from this week’s conversation is that technology isn’t your message—your customer’s problem is. Dunford’s classic on positioning helps businesses articulate exactly why their solution matters, regardless of how sophisticated the technology behind it may be.

More to explore

If you’d like to dive deeper into Sam Yeruva’s work, here are a few great places to start:

• Pycube

• Sam on LinkedIn

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

For a long time, leadership followed a fairly predictable script. You learned the job, proved yourself over the course of a few years, and eventually someone trusted you with more responsibility. A new title appeared on your business card, a few people reported to you, and only then were you expected to think like a leader. Until that moment, your job was execution. Direction belonged to someone else.

That arrangement made sense when organizations were built around hierarchy. Decisions traveled from the executive suite through layers of management before they reached the people doing the work. If you had an idea, there was usually a process for sharing it. If you saw a problem, there was probably someone above you who was responsible for solving it. Waiting your turn wasn’t a weakness. It was simply how work was organized.

It doesn’t feel that way anymore.

Most organizations have become flatter, faster, and far less patient. Managers oversee larger teams. Companies expect fewer people to accomplish more. Projects move before everyone feels ready, and the distance between identifying a problem and solving it has grown shorter than the distance between identifying a problem and asking for permission to solve it. In that kind of environment, initiative has become one of the most valuable professional skills a person can possess.

What’s striking is that initiative rarely announces itself. It looks remarkably ordinary. It’s the employee who notices the customer isn’t getting an answer and picks up the phone instead of forwarding another email. It’s the teammate who walks into a confusing meeting and leaves everyone with a clear next step. It’s the person who consistently follows through, who makes deadlines feel dependable instead of aspirational, who quietly becomes the colleague everyone hopes is assigned to the next project.

Those people often end up leading long before anyone gives them a leadership title.

I don’t think that’s because organizations have suddenly lowered their standards for leadership. Quite the opposite. They’ve simply become better at recognizing where leadership actually begins. It isn’t in authority. It isn’t in organizational charts. It starts much earlier, in the small decisions people make every day to reduce friction, solve problems, and make the people around them more effective. Promotions tend to recognize those habits—not create them.

Few people describe that shift better than Eggs! The Podcast guest, Greg Hoover. After spending decades leading organizations ranging from family-owned businesses to nearly billion-dollar enterprises, Hoover has become convinced that leadership isn’t something that’s granted. It’s something that’s practiced. His philosophy, which he calls Lead Anyway, is built around a simple premise: the people who create the greatest impact are rarely the ones waiting to be asked.

Leadership Is Built Long Before It’s Recognized

Greg Hoover has spent more than three decades in executive leadership, serving as a Chief Operating Officer, Chief Marketing Officer, President, and Chief Executive Officer across organizations ranging from a family-owned business to Atlas Van Lines, where he helped lead a company approaching $1 billion in annual revenue. Today, through his consulting firm, Third Star, he advises organizations on leadership development, organizational clarity, and building cultures that consistently execute at a high level.

What’s refreshing about Hoover’s perspective is that it isn’t built around executive theory or management jargon. It was forged by watching thousands of people succeed—or fail—in real organizations. Again and again, he found that the individuals who became indispensable weren’t always the most talented or the ones with the most impressive titles. They were the people who showed up consistently, communicated clearly, earned trust, and made the people around them better. Those observations eventually became the foundation of his book, Lead Anyway: Ordinary You, Extraordinary Impact, a practical argument that leadership is less about authority than it is about everyday decisions.

Our conversation explores why simplicity often beats complexity, why influence matters more than hierarchy, and why the strongest leaders are usually practicing leadership long before anyone officially calls them one. It’s a timely reminder that in today’s workplace, initiative is no longer a nice quality to have—it’s quickly becoming the price of admission.

Leadership Happens in the Small Moments

The biggest ideas in this conversation aren't about becoming a CEO or climbing an organizational chart. They're about the habits that quietly earn trust over time. Here are a few moments from my conversation with Greg that stood out—and the practical lessons they hold for anyone trying to make a greater impact.

“You don't get promoted by waiting for permission, waiting for a title, or waiting for somebody to anoint you as the guy in charge of the project.”

Actionable insight: If there's a problem you know how to solve, solve it. Leadership rarely begins with authority; it begins with someone deciding they're willing to own the outcome before anyone tells them to.

“Leadership becomes about how much we're all on the same page as opposed to having ten best players in the game.”

Actionable insight: Talent scales poorly without alignment. Before adding another person, another tool, or another meeting, ask whether everyone actually understands the mission. Clarity almost always outperforms complexity.

“If you see a fire, do you stand around and wait for the fire truck, or do you look for a hose?”

Actionable insight: Initiative doesn’t require permission. The most valuable people in any organization are the ones who instinctively move toward the problem instead of assuming someone else will handle it.

“Leadership is showing up in practice day after day and doing the repetitions. It's in the small things.”

Actionable insight: We tend to celebrate the visible moments—the promotion, the keynote, the championship—but careers are built in the ordinary moments nobody notices. Show up early. Keep your commitments. Repeat until people stop seeing it as effort and start seeing it as who you are.

“I'd rather that we execute fully and completely at 80% than spend all our time trying to grind out that last 15 or 20 and be perfect.”

Actionable insight: Perfection is often procrastination wearing nicer clothes. Ship the proposal. Make the call. Publish the idea. Momentum is almost always more valuable than polishing something that never leaves your desk.

“Be beyond reproach. Do the right things and don't worry about the rest of it. The rest will take care of itself.”

Actionable insight: Reputation is accumulated long before it's tested. When you're consistently dependable, ethical, and prepared, trust becomes your greatest professional advantage—and the opportunities tend to follow.

Don't Wait to Be Chosen

One of the biggest misconceptions in business is that leadership starts with a promotion. It doesn’t. Promotions simply make visible what has often been true for months—or years. By the time someone is entrusted with greater responsibility, they’ve usually spent a long time demonstrating that they can be trusted with smaller ones. They’ve built a reputation for showing up, following through, and making life easier for the people around them. That’s rarely glamorous work, but it’s almost always the work that matters most.

There’s something freeing about that realization. It means you don’t have to wait for the next title, the next opportunity, or the next stage of your career before deciding what kind of leader you want to become. Every meeting, every client conversation, every difficult project offers another chance to build trust or erode it. The cumulative effect of those seemingly ordinary moments is what shapes a career far more than any single breakthrough ever will.

The permissionless workplace isn’t asking us to become louder, busier, or more visible. It’s asking us to become more dependable. To raise our hand before we’re asked. To bring clarity where there’s confusion. To quietly make the people around us better. Those aren’t just leadership traits—they’re the habits that earn the opportunity to lead in the first place.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch Kate’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Lead Anyway — Greg Hoover

   Naturally, this week’s conversation begins here. Hoover makes the case that leadership isn’t reserved for executives or managers. It’s a daily choice to bring energy, clarity, and accountability to whatever role you’re in. Practical, approachable, and full of lessons that apply whether you’re leading a company or simply trying to become someone others can depend on.

2. The Motive — Patrick Lencioni

   One of the shortest—and most impactful—leadership books I’ve ever read. Lencioni asks a deceptively simple question: Why do you want to lead? If the answer is status instead of responsibility, you’re likely chasing the wrong prize. A great companion to Greg’s philosophy that leadership begins long before the title arrives.

3. Turn the Ship Around! — L. David Marquet

   Marquet transformed one of the worst-performing submarines in the U.S. Navy by abandoning the traditional command-and-control model in favor of distributed leadership. Rather than waiting for orders, every sailor was expected to think, contribute, and take ownership. It’s one of the best real-world examples of what a permissionless workplace can look like.

4. Essentialism — Greg McKeown

   Greg Hoover returns repeatedly to the power of simplicity. McKeown explores the same principle from a different perspective: the disciplined pursuit of what matters most. If your calendar, inbox, or project list constantly feels overwhelming, this book offers a compelling argument that doing less—better—is often the fastest path forward.

5. The Score Takes Care of Itself — Bill Walsh

   Walsh built one of the greatest dynasties in NFL history, but his philosophy wasn’t centered on winning. It was centered on mastering the process. Focus relentlessly on standards, preparation, and execution, and the results eventually take care of themselves. That mindset echoes throughout this week’s conversation with Greg.

More to explore

If you’d like to dive deeper into Greg Hoover’s work, here are a few great places to start:

• Lead Anyway: Ordinary You, Extraordinary Impact (Amazon)

• Third Star Consulting

• Greg Hoover on LinkedIn

Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

One of the stranger things about modern business is how often companies teach people to distrust themselves, then sell them something to fix the problem they helped create.

Fitness is probably the cleanest example. For decades, the industry has run on a pretty simple emotional engine: point out the flaw, make it feel urgent, then offer the plan, product, supplement, trainer, app, meal system, challenge, or whatever else as the way out. The message changes depending on the era. In the nineties, it was fat-free everything and the moral panic around eating the wrong thing. Then came low carb, keto, carnivore, macros, protein targets, wearables, cold plunges, red lights, peptides, and a long list of other things that may or may not be useful depending on the person. The pattern, though, stays mostly intact. Something is wrong with you. Someone else has the answer. You are one purchase away from becoming the kind of person you were supposed to be.

That kind of marketing works. We should be honest about that. If it didn’t, the industry wouldn’t keep returning to it. Shame moves people. Fear moves people. Confusion moves people. A person who feels bad about their body, their business, their bank account, their discipline, their parenting, their leadership, or their future is much easier to convert than a person who feels grounded and clear. That is not limited to fitness. Agencies do it when they make clients feel behind for not chasing the newest platform. Consultants do it when they turn complexity into dependency. Software companies do it when every product is framed as the one thing standing between you and irrelevance. Even leadership content does it, just with better lighting and more Patagonia vests.

The problem is that the thing you use to acquire a customer often becomes the emotional frame through which they experience the product. If you sell someone by convincing them they are failing, they do not magically become confident when the receipt hits their inbox. They bring the failure story with them. Now every missed workout confirms it. Every stalled campaign confirms it. Every confusing dashboard, every missed goal, every imperfect quarter becomes more evidence in the case they were already building against themselves. You may have sold them a solution, but you also gave them a script.

That script is expensive. It creates customers who need to be rescued over and over again. It creates brands that have to keep finding new insecurities to press on because the relationship itself was never built on trust. It creates churn disguised as growth. The numbers can look good for a while, especially if the funnel is sharp and the market is big enough, but a business built this way is always hungry. It has to keep replacing the people it disappointed, overwhelmed, or quietly made feel worse.

This is where the conversation about AI gets interesting, because the obvious fear is that AI will make expertise cheap. And it will. In many categories, it already has. A workout plan, a meal plan, a marketing plan, a sales script, a hiring scorecard, a pitch deck, a content calendar — all of it can now be produced almost instantly. Some of it will be decent. Some of it will be nonsense. Most of it will arrive with enough confidence to make the average person wonder if they are the problem for not knowing the difference.

But if knowledge gets cheaper, the value of a business does not disappear. It moves. The value moves into judgment. Into context. Into taste. Into whether the customer believes you are telling them the truth or simply nudging them toward the highest-converting option. In a market full of answers, the business that can say, “This is not what you need,” may prove more valuable than the one with the fastest answer.

That sounds moral, and maybe it is, but it is also practical. Trust lowers drag. People return to places where they feel safe, understood, and not constantly manipulated. They tell their friends about businesses that make them feel more capable, not smaller. They forgive mistakes when they believe the intent behind the work is real. They stay longer when the product helps them build a better relationship with the problem they came to solve.

Eggs! The Podcast guest and business leader Tyler Bramlett, better known to many as Coach Tyler, has lived both sides of that equation. He built a highly successful fitness business using the kind of messaging the industry has rewarded for years, then reached a point where the success no longer felt clean. The business worked, but the work itself began to raise harder questions: Was it helping people get healthier, or just teaching them to hate themselves more efficiently? Was it building something durable, or simply riding the next wave of insecurity until the market moved on?

Those questions eventually became WeShape, a fitness company built around personalized movement, technology, and a very different premise: people do not need to punish themselves into becoming worthy of care. In a category full of hacks and hard sells, Tyler is making a more difficult bet — that a business can grow by helping people feel less broken, not more. And in an age where advice is everywhere, that may be one of the few advantages still worth building around.

From Performance to Purpose

The roots of WeShape go back to a much less polished version of the fitness story. Tyler grew up without much of a roadmap for health, joking that in his house, diet soda was treated like a reasonable wellness choice. He learned the early language of fitness the way a lot of people did before social media: magazines, bodybuilding books, borrowed routines, and a fair amount of trial and error. At first, the goal was familiar enough — build the body, prove the discipline, look the part.

That changed after he was hit by a car. Coming back from that injury, fitness became less about appearance and more about function. The gym was no longer just a place to chase strength or aesthetics; it became a place to figure out how to move without pain. Tyler used the settlement from that accident to travel the country, learning from physical therapists, athletic trainers, and movement specialists. What stayed with him was the importance of progression, personalization, and meeting people where their bodies actually are.

That foundation eventually led him from personal training to a successful group fitness business, then into online fitness products and an eight-figure company that made the Inc. 500 list three years in a row. By the normal measures, the business was working. But success also made the gap harder to ignore. The company could keep selling what the market rewarded, or it could question whether the message underneath the sale was doing real damage. WeShape was born from that question, and from the decision to build a fitness company around care, trust, and sustainable change instead of shame.

What the Customer Learns From the Way You Sell

The best parts of this conversation are not really about fitness. They are about the relationship between message, trust, and the kind of customer experience a company is quietly teaching people to expect.

“Everything hurt. Everything just felt horrible in my body. I quickly realized this isn’t going to go away.”

Actionable insight: Pay close attention to the moment when the customer’s problem becomes real, not theoretical. In fitness, that may be pain. In business, it may be missed revenue, wasted spend, a stalled team, or a strategy that looked good in the deck but collapsed in practice. The better offer usually starts where the customer is actually hurting, not where the market prefers to talk.

“I realized some really common themes amongst everybody’s training modalities. There’s always a progression, and everybody needs something that’s unique to them.”

Actionable insight: Most customers do not need a more intense version of the same generic answer. They need the right next step. Build products, services, and onboarding systems that account for progression, because what works for an advanced customer may overwhelm a beginner and underwhelm someone who is already capable.

“One of the hardest things to do as an entrepreneur is look in the mirror and say, am I actually showing up and serving my purpose here, or am I showing up and serving myself?”

Actionable insight: A profitable offer can still be misaligned. That does not mean every business needs to become some grand moral crusade, but it does mean founders should be honest about whether the company is solving a problem or simply getting better at pressing on one.

“If I got no money, no praise, no nothing from this, what would I genuinely want to build?”

Actionable insight: This is a useful pressure test, especially when the business is already working. Strip away the applause, the revenue, the status, and the external validation. What remains is usually a much clearer signal about what kind of company you actually want to spend the next decade building.

“The cost of knowledge is quickly dropping to zero. And so if the cost of knowledge is zero, what is the value of any business that’s service related? It’s not the knowledge, it’s the trust.”

Actionable insight: In the AI age, information is no longer much of a moat. The advantage moves to judgment, context, care, and credibility. If your business is built only on having answers, it is vulnerable. If it is built on being trusted with the answer, that is harder to replace.

“Every single time I tell the truth, and especially if I tell the truth in a way that doesn’t serve me, I’m building trust.”

Actionable insight: The most valuable trust-building moments are often the ones where the company could have taken the easy sale and didn’t. Telling someone they are not a fit, not ready, or better served somewhere else may cost revenue today, but it creates the kind of reputation that compounds.

“If you build something great, people stay. They tell their friends. They want to be a part of it.”

Actionable insight: Retention is not just a metric on a dashboard. It is evidence that the customer experience is strong enough to survive beyond the initial promise. If people only buy once, the marketing may be working. If they stay, return, and refer, the business is working.

“Take action on the basics consistently.”

Actionable insight: Most companies do not need a more exotic strategy. They need to do the ordinary things with more discipline: talk to customers, improve the product, publish the content, refine the offer, fix the handoff, follow up, measure what matters, and repeat. Not glamorous. Usually effective.

The Business You’re Really Training People to Trust

The easy move is to look at Tyler’s story as a fitness industry correction, and it is that. But the bigger lesson is more useful than that. Every business is teaching its customers something before the product ever has a chance to work. It teaches them whether they are safe asking questions. Whether the company is telling the truth. Whether the relationship is built on progress or pressure. Whether the brand sees them as a person to serve or a problem to convert.

That is going to matter more, not less, as the tools get faster and the answers get cheaper. The companies that rely on confusion, urgency, or insecurity may still win plenty of transactions. Some will do very well. But the businesses worth building — the ones with depth, loyalty, referrals, and staying power — will be the ones that help people feel more capable after the sale than they did before it.

That is a harder standard. It asks more of the founder, the team, the product, and the message. But it also gives the work a chance to become something more durable than a clever campaign or a well-timed trend. In the end, people remember who made them feel small, and they remember who helped them stand a little taller.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

Ready for more?

Catch Kate’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Focused as a Bee — Jones Loflin and Sydney Loflin The natural companion to this week’s conversation. Loflin uses the structure and behavior of honeybees to explore focus, distraction, and the cost of spending our days on work that looks productive but does not actually move us where we want to go.

2. Juggling Elephants — Jones Loflin and Todd Musig A practical parable built around the three-ring circus metaphor Jones referenced in our conversation: work, self, and relationships. It’s a good read for anyone who feels like every part of life is competing for the same limited supply of attention.

3. A Minute to Think — Juliet Funt A strong argument for white space as a business advantage. Funt makes the case that constant activity is not the same as value, and that better thinking often starts when we stop filling every open minute with another task.

4. Essentialism — Greg McKeown A clean, useful book about the disciplined pursuit of less. Not less ambition. Less noise. Less accidental commitment. Less work that only exists because nobody stopped to ask whether it still mattered.

5. Building a Second Brain — Tiago Forte Jones referenced Forte’s CODE framework — collect, organize, distill, express — and it fits nicely here. This is a good pick for anyone who has too many ideas, too many inputs, and no reliable system for turning raw material into useful output.

6. Psycho-Cybernetics — Maxwell Maltz A classic on self-image, confidence, and the invisible walls we build in our own minds. A little old-school in places, but still valuable if you keep running into the same internal barrier right before the work gets real.

More to explore

• The Trusted Advisor — David H. Maister, Charles H. Green, and Robert M. Galford
  This is the obvious business companion to the issue. If knowledge is getting cheaper, trust becomes the thing that separates the disposable service provider from the person or company people actually rely on. This book is especially useful for consultants, agencies, coaches, and anyone whose work depends on credibility before the sale and confidence after it.

• The Go-Giver — Bob Burg and John David Mann
  Ryan mentioned this one in the conversation, and it fits cleanly with Tyler’s larger point about building from service instead of self-interest. It is a short, simple business fable, but the idea underneath it is not small: the most durable businesses tend to create more value than they extract.

• Quit: The Power of Knowing When to Walk Away — Annie Duke
  Tyler’s story is not just about starting something new. It is about walking away from something that was already working by the usual measures. Annie Duke’s book is a useful counterweight to the usual “never quit” advice, especially for founders who may be holding onto a product, offer, customer segment, or identity simply because it has already cost them so much..

• Atomic Habits — James Clear
  This one is almost too obvious to include, but Tyler’s “take action on the basics consistently” line makes it hard to leave out. The book is useful because it takes improvement out of the world of heroic reinvention and puts it back where it usually belongs: small behaviors, repeated often enough to become identity.

• The Long Game — Dorie Clark
  For anyone building something that will not reward them immediately, this is a good one to keep nearby. Clark writes about patience, strategic persistence, and the discipline of doing work that may not look impressive in the moment. That pairs well with the tension in Tyler’s story: the faster, easier business worked, but the slower, harder one had the better chance to last.

  
  Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
  Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

There was a time when being busy was seen as a pretty decent proxy for being important.

The packed calendar. The late-night email. The laptop open at dinner. The casual mention that you “haven’t had a day off in weeks.” For a long stretch there, especially in entrepreneurial circles, those things became a kind of social proof. If you were exhausted, you must have been building something. If you were unavailable, you must have been in demand. If you were buried, you must have been valuable.

I bought into that more than I care to admit.

For years, my default mode was: go. Sit down. Make the thing. Build the website. Design the brand. Ship the work. Take the call. Answer the message. Start the next idea. Keep moving. And to be fair, execution matters. A lot. Nothing gets built in theory. But execution can also become a hiding place. It lets you feel productive without forcing you to ask the harder question: productive toward what?

That is where a lot of us get into trouble. Not because we’re lazy or lack ambition. In fact, it’s usually the opposite. The problem is that work has become so frictionless, so immediate, and so constantly available that we can fill every spare inch of the day without ever deciding whether the work deserves to be there. We confuse motion for progress because motion gives us a receipt. Progress is harder to measure in real time.

A full calendar can hide an empty strategy, and this is especially true now, when tools make it easier than ever to produce more. AI can help us write faster, design faster, prototype faster, research faster, automate faster. All useful. But speed has a way of making poor choices look impressive. If you are pointed in the wrong direction, acceleration is not a gift. It just gets you farther from the thing you actually meant to build.

That’s the real productivity conversation I think more of us need to have. Not how to squeeze another hour out of the day. Not how to wake up at 4:30, journal by candlelight, cold plunge, answer emails, and pretend we’re all operating like Navy SEALs with LLCs. The better question is simpler and more uncomfortable: what am I choosing, and what is that choice costing me?

Because every yes is funded by something. Sometimes it’s sleep. Sometimes it’s health. Sometimes it’s the business development work you keep avoiding because execution feels safer. Sometimes it’s your spouse, your kids, your friends, your body, your own ability to sit quietly for ten minutes and think clearly about where your life is headed.

The backlash against busywork is not a rejection of hard work. Hard work still matters. It always will. But hard work without direction is just endurance. The next advantage belongs to the people who can tell the difference between being busy and being aligned; between reacting and choosing; between doing more and doing what matters.

That is why the conversation with Eggs! The Podcast guest, leadership coach, and author, Jones Loflin, feels so useful. Jones has spent decades helping leaders, teams, and entrepreneurs make better choices with their time, energy, and attention. His language is simple, but the implications are not. In a culture addicted to activity, he makes a case for something much more valuable: focus.

From Busy to Focused

Jones Loflin is an author, keynote speaker, and executive coach whose work centers on leadership development, time management, work-life success, and the daily choices that shape professional and personal outcomes. Over nearly thirty years, he has worked with audiences and organizations looking to get clearer about where their energy is going and whether that energy is actually producing the results they want.

His latest book, Focused as a Bee, builds on a simple but useful contrast: most people know what it feels like to be busy, but far fewer know what it means to be truly focused. In our conversation, Jones used the metaphor of a three-ring circus — work, self, and relationships — to explain how easily people get trapped in one ring while neglecting the others. The point is not perfect balance. It is knowing where you need to be, when you need to be there, and what deserves your best attention in that moment.

What makes Jones’ perspective especially relevant now is that he does not treat productivity as a mechanical problem. This is not another conversation about inbox hacks or calendar tricks. It is about agency. The ability to stop, think, choose, and realign before the day fills itself for you.

The Work That Deserves Your Attention

Jones’ best ideas come back to a deceptively simple premise: focus is not a productivity hack. It is a choice. And most of the time, the better choice starts by admitting how much of the day is running on autopilot.

“Too often, we get automated with our schedules, with our activities, with the things we do in our day, and we don’t stop and ask ourselves, are these the activities that are going to contribute to the business success or team success that I really want?”

Actionable insight: Audit the recurring work before adding more of it. The standing meeting, the weekly report, the daily scramble — some of it may still matter, but some of it is probably just there because nobody has been brave enough to question it.

“You are the ringmaster of your circus. That doesn’t mean you’re in control of everything. But it does mean you are in control of certain parts of your day, your time, your energy.”

Actionable insight: Control is rarely total, but it is also rarely zero. Start by naming the parts of your day you actually can influence, then protect those like they matter. Because they do.

“It’s not about balance in your life. It’s about being in the right ring at the right moment.”

Actionable insight: Work-life balance gets messy because life is messy. A better measure may be presence. When it’s time to work, work. When it’s time to recover, recover. The leakage between the two is where a lot of energy quietly disappears.

“In your drive to get it all done, what’s not getting done or not getting done well?”

Actionable insight: This is the question that exposes the cost of busyness. If the strategic work, the health work, the relationship work, or the business development work is always the thing getting pushed, your calendar is telling on you.

“Some of your best ideas come up when you disconnect, when you’re exercising, when you’re taking a walk outside.”

Actionable insight: Thinking time is not wasted time, especially for leaders, founders, and creatives. Execution may happen at the desk, but the idea often shows up in the shower, on a walk, or during the ten quiet minutes you keep refusing to take..

“I think the challenge for many people is they want to be able to choose step fifteen when right now they need to choose step number two.”

Actionable insight: Big outcomes usually get blocked by small avoidance. Don’t wait until the whole path is visible. Send the rough draft, make the call, test the offer, ask the question. Step two has more answers in it than another week of overthinking.

“Every action that every bee takes is aligned toward the outcomes they want.”

Actionable insight: That is a brutal little standard for a workday. If the outcome matters, the actions should point toward it. If they don’t, the problem may not be effort. It may be alignment.

Choose the Work That Chooses Back

The point is not to abandon ambition or soften the edges of what it takes to build something meaningful. Business still rewards people who can execute, endure, and keep moving when the work gets hard. But there is a difference between discipline and drift. One is chosen. The other just happens to you.

That may be the real danger of busywork. It does not usually feel wasteful in the moment. It feels responsible. It feels productive. It feels like proof that you’re doing your part. But over time, the bill comes due. The strategy gets thinner. The relationships get quieter. The body keeps score. The bigger idea waits in the corner while you answer one more email.

The better path is not less work. It is more honest work. Work pointed at something. Work chosen with intention. Work that leaves enough room for thought, health, people, and the occasional quiet moment where the next right move finally has enough space to appear.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

Ready for more?

Catch Kate’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

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Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Focused as a Bee — Jones Loflin and Sydney Loflin The natural companion to this week’s conversation. Loflin uses the structure and behavior of honeybees to explore focus, distraction, and the cost of spending our days on work that looks productive but does not actually move us where we want to go.

2. Juggling Elephants — Jones Loflin and Todd Musig A practical parable built around the three-ring circus metaphor Jones referenced in our conversation: work, self, and relationships. It’s a good read for anyone who feels like every part of life is competing for the same limited supply of attention.

3. A Minute to Think — Juliet Funt A strong argument for white space as a business advantage. Funt makes the case that constant activity is not the same as value, and that better thinking often starts when we stop filling every open minute with another task.

4. Essentialism — Greg McKeown A clean, useful book about the disciplined pursuit of less. Not less ambition. Less noise. Less accidental commitment. Less work that only exists because nobody stopped to ask whether it still mattered.

5. Building a Second Brain — Tiago Forte Jones referenced Forte’s CODE framework — collect, organize, distill, express — and it fits nicely here. This is a good pick for anyone who has too many ideas, too many inputs, and no reliable system for turning raw material into useful output.

6. Psycho-Cybernetics — Maxwell Maltz A classic on self-image, confidence, and the invisible walls we build in our own minds. A little old-school in places, but still valuable if you keep running into the same internal barrier right before the work gets real.

More to explore

• Focused as a Bee — Get the Book
  Jones’ newest book on focus, distractions, and making better use of your time and energy.

• Juggling Elephants — Get the Book
  The book behind Jones’ three-ring circus framework for work, self, and relationships.

• Jones Loflin — Official Website
  Learn more about Jones’ speaking, coaching, books, and resources.

• Jones Loflin on LinkedIn
  Connect with Jones and follow his ongoing posts about focus, overload, leadership, and better choices with time.

• Jones Loflin on YouTube
  Short videos and teaching clips from Jones on focus, work-life success, and leadership.

  
  Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
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For the last decade or so, a lot of business strategy has been built around the idea of removing people from the process. We automated the follow-up. We optimized the funnel. We bought the ads, studied the dashboards, built the landing pages, hired the influencers, tested the headlines, chased the algorithm, and celebrated every point of friction we could eliminate between a customer wanting something and a company taking their money. Some of that was useful. A lot of it still is. But somewhere along the way, the tool started getting mistaken for the relationship.

That was always the danger. Digital marketing gave businesses reach they never had before, and reach is intoxicating. It makes the world feel bigger and more available. It lets a small brand find customers three states away, or three countries away, before lunch. But reach is not the same thing as trust. Visibility is not the same thing as credibility. A customer clicking “buy now” is not always the same as a customer believing in what they bought, who they bought it from, and why it should matter beyond the transaction.

Commerce was human long before it was digital. That sounds obvious, but business has a way of forgetting obvious things when a new platform shows up with a dashboard and a growth curve. For most of history, buying something meant dealing with another person. A shopkeeper. A maker. A neighbor. A salesperson who had to look you in the eye and stand behind the thing they were selling. Reputation had weight because it lived in the real world. If the product was bad, if the promise was thin, if the experience felt cheap or dishonest, there was nowhere to hide. You had to face the customer again.

The internet didn’t erase that truth. It just made it easier to ignore for a while. We could dress up weak products with strong branding. We could inflate mediocre ideas with paid attention. We could throw a few affiliate codes at an influencer campaign and pretend that enthusiasm had been earned. We could push customers into automated service loops and call it efficiency. And for a while, a lot of it worked well enough to keep everyone moving. But people eventually develop a feel for thinness. They know when the review sounds bought. They know when the “community” is really just a retargeting list. They know when a company has optimized everything except the part where it actually has to be good.

That’s why the movement back toward human-centered commerce feels less like nostalgia and more like a correction. It’s not about pretending Amazon doesn’t exist, or that ads don’t work, or that automation is somehow immoral. That would be silly. The issue is proportion. Tools should extend trust, not replace it. Marketing should help a good product find the right people, not create a fog machine around something forgettable. Growth should widen the circle without hollowing out the center. When businesses get that backward, they may still sell, but they lose the thing that makes people come back, talk about it, defend it, and feel good being associated with it.

The brands that understand this tend to have a different relationship with scale. They are not allergic to growth, but they are careful about what growth asks them to trade away. They know the channel matters. They know the buying experience matters. They know that a little friction can be useful if it creates intention, confidence, or discovery. A customer walking into a trusted local shop and being told, “Yes, I’ve tried this, and it works,” is a very different kind of conversion than a customer being chased around the internet by an ad for something they barely remember clicking on. One is attention. The other is trust.

That distinction sits at the heart of my conversation on EGGS! The Podcast with Kate Assaraf, founder and CEO of Dip Sustainable Hair Care. Kate built Dip around a product that had to be excellent before its mission could matter, then grew the company through independent retailers, refill shops, salons, surf shops, and word of mouth rather than the usual race toward Amazon and big-box scale. Her story is not a rejection of modern commerce. It’s a reminder that the human layer was always the anchor. We drifted away from it because the new tools were shiny, fast, and measurable. Now the smarter brands are starting to remember what the best ones never forgot.

Where Trust Lives On

Kate Assaraf is the founder and CEO of Dip Sustainable Hair Care, a plastic-free hair and personal care brand built for people who have grown tired of sustainability products that ask too much and deliver too little. After more than 20 years in the beauty industry, Kate saw the same problem from both sides: consumers wanted to make better choices, but too many “better” products were underperforming, over-marketed, or built more around the sustainability claim than the actual customer experience.

Dip was her answer to that gap. Rather than reverse-engineering a product to hit a convenient price point, Kate worked with a chemist experienced in salon-quality hair care and started with a different question: What would the best version of this product be if the price point wasn’t the first constraint? That approach led to oversized, long-lasting shampoo and conditioner bars designed to work well enough that the plastic-free part almost became secondary.

What makes Kate’s story especially interesting is not just the product, but the path she chose to grow it. Dip has largely avoided the default modern playbook — Amazon, big-box retail, fake influencer hype, and endless ad spend — in favor of independent refill stores, salons, surf shops, real customer relationships, and word of mouth. In doing so, Kate has built more than a sustainable hair care company. She has built a case study in what happens when a brand protects the human relationship at the center of the transaction.

The Work Beneath the Word of Mouth

Kate’s approach works because it is not built around a single tactic. It is a set of choices that all point in the same direction: better product, better context, better relationships, and a refusal to confuse attention with trust.

“People were leaving sustainability and just returning back to their plastic-clad items. My goal with Dip was to make something so good that the plastic-free part of it didn’t even matter.”

Actionable insight: A mission can open the door, but the product still has to earn its place in someone’s life. If the thing itself does not work, the values story eventually becomes a burden instead of an advantage.

“Big part of the story is that this is really good. It’s made with great ingredients, it’ll last you a long time, and it’ll save you money.”

Actionable insight: The strongest positioning is often simpler than we make it. Before dressing a brand in purpose, personality, or cultural relevance, make sure the basic customer argument is clear: it works, it lasts, and it makes sense.

“I was like, let’s make the best bar ever, regardless of what the price is going to be. I didn’t start by building backwards and subtracting all the bells and whistles until we could meet a marketing price point.”

Actionable insight: Price matters, but building only toward a price point can quietly strip the product of the very thing that would have made people care. Sometimes the better question is not “How cheap can we make this?” but “How good does this need to be for people to talk about it without being asked?”

“I made the value for the consumer, not for me. And I was banking on the consumer being so excited about it that they would tell others.”

Actionable insight: Word of mouth is not a campaign. It is the result of a customer feeling like they got more than they expected. That does not happen by accident, and it rarely happens when every decision is made to protect the seller’s margin first.

“I call it like refill stores are the new record store. If you remember back in the day when you wanted to find something cool in music, you would go to the record store and talk to the person behind the counter. It’s like that in sustainability now.”

Actionable insight: Discovery still has a human shape. The best retailers do more than stock shelves; they transfer confidence. They help customers make sense of choices in a market that is crowded, loud, and increasingly hard to trust.

“I’m not anti-corporation, but the moment I put Dip on Amazon, people will flock to Amazon to buy it and not to the refill stores, where I know sustainability matters the most.”

Actionable insight: Distribution is not neutral. Where a product is sold changes the relationship around it, the expectations attached to it, and the ecosystem it supports. More access is not always better if it weakens the channel that made the brand meaningful in the first place.

“Growth was a by-product. It wasn’t the goal. My goal was to support as many refill stores, independent salons, and surf shops as possible.”

Actionable insight: Growth without a center tends to become appetite. Growth with a point of view has boundaries, and those boundaries can become part of the brand’s strength. The question is not simply how big the company can get, but what has to remain intact as it grows.

The Human Part Was Never Optional

There is nothing wrong with scale. There is nothing wrong with using the tools available to reach more people, sell more products, or make a company more efficient. But scale has a way of testing what a business actually believes. If the product gets thinner, the customer gets farther away, the channel gets weaker, and the relationship becomes less important than the transaction, the company may still grow — but it grows by loosening its grip on the thing that made it worth caring about in the first place.

That is what makes Kate’s story useful. Dip is not a museum piece or a protest against modern business. It is a functioning, growing company built around an older truth: people still want to buy good things from people they trust. The platforms will keep changing. The tools will keep getting faster. The dashboards will keep promising cleaner answers than real life can usually provide. But the anchor is still human. It always was.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

Ready for more?

Catch Kate’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Small Giants — Bo Burlingham This is probably the cleanest companion to this week’s conversation. Burlingham looks at companies that chose to be great instead of simply chasing size, which makes it a natural fit for a founder story built around independent retail, intentional growth, and knowing what not to trade away.

2. The Human Brand — Chris Malone and Susan T. Fiske A smart look at why people relate to companies in deeply human terms. The book’s core idea — that customers judge brands through signals of warmth and competence — lines up nicely with the larger argument here: trust is not an accessory to commerce. It is the thing commerce runs on.

3. Let My People Go Surfing — Yvon Chouinard Chouinard’s Patagonia story is still one of the best examples of building a real company around values without letting the values become empty marketing. It pairs especially well with Dip’s “buy better, buy less, shop small” philosophy.

4. The Experience Economy — B. Joseph Pine II and James H. Gilmore A classic for thinking about the difference between a transaction and an experience. That distinction matters here because a customer buying from a trusted local shop is not having the same experience as someone clicking “buy now” from the cheapest listing in a feed.

5. The Thank You Economy — Gary Vaynerchuk This one is a little older now, but the central idea has aged well: businesses win when they remember that customer relationships are not abstract. Listening, responding, being honest, and making people feel seen still matter, even when the channels change.

More to explore

• Dip Sustainable Hair Care — Kate Assaraf’s plastic-free hair and personal care brand, built around performance first and sustainability as something more durable than a marketing angle.

• Find Dip near you — Use Dip’s store locator to find independent refill stores, salons, surf shops, and boutiques carrying the brand.

• Why Refill Is the New Record Store — Dip’s own piece on why refill stores matter as places of discovery, community, and human-to-human trust.

• Small Thinking — A deeper look at Dip’s point of view on shopping small, building differently, and resisting the pressure to flatten everything into scale.

• Kate Assaraf on LinkedIn — Follow Kate’s thinking on ethical entrepreneurship, sustainability, and building a brand outside the usual beauty-industry playbook.

• Dip on Instagram — Product updates, brand personality, and a good look at how Dip shows up visually.

• Dip on TikTok — More from the Dip world, including product education and behind-the-scenes brand content.

  
  Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
  Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://rogha.ar

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

Three essays in, and the picture of The Lid is complete enough to work with. You know what it is. You know where it came from. You know why it stays. And despite all that, you know that just seeing it clearly doesn’t make it fade away — that recognition may generate a brief window of momentum, but then the same mechanisms reassert themselves, because they were never about ignorance in the first place.

So the obvious question is: what do you actually do?

I want to be careful here about what kind of answer I’m offering. I haven’t passed my own Lid. I’m writing this from inside the same pattern I’ve been describing, not from the other side of a breakthrough. What I can give you is what the research shows actually moves the needle on the specific mechanisms we’ve been talking about — and what I’m attempting to do with that information. Not a system with a name. Just things that are aimed at the right targets.

Start with the right diagnosis

The single most important move in the method isn’t an action. It’s a distinction.

Essay 1 described The Lid as having two faces — internal and external. The internal face is identity, self-concept, the accumulated sense of what belongs to you and what doesn’t. The external face is structural: missing information, missing exposure, no map for what the next level actually looks like from the inside. Both can maintain The Lid. Both require attention. But they don’t require the same response, and applying the wrong one to the wrong problem is a way of staying stuck while feeling productive.

If you can’t articulate what the next step looks like — if the move you’re not making is genuinely unclear or if you’ve never seen someone navigate this transition and don’t have a working model for how it goes — that’s an information problem. The fix is exposure, not introspection.

If you can describe the next step precisely, if you’ve watched others take it, if you know more or less what it requires and still haven’t done it — that’s identity. The system is protecting you from becoming someone it hasn’t agreed to become yet. That needs different work.

Most of the time, it’s both. But it’s common for one to be doing more of the blocking. Getting that diagnosis right — honestly, without letting either explanation become a hiding place — is where the method begins.

Make the other side concrete

Essay 3 named the fog: the other side of The Lid isn’t dark, it’s fuzzy. You can see shapes, not details. And that fuzziness weakens the pull toward it, because we are not strongly motivated by destinations we can’t clearly see.

The research on possible selves — the mental images we carry of who we might become — shows that specificity is what gives those images their motivational force. A vague picture of a better version of your life doesn’t pull very hard. A specific one does. The difference isn’t optimism. It’s resolution.

Peter Gollwitzer’s work on implementation intentions makes the same point from a different direction. Across nearly a hundred studies, people who specified not just what they intended to do but exactly when, where, and under what conditions were dramatically more likely to follow through than people who held only a general intention. Specificity is the mechanism, not a detail.

What this looks like practically: you build a concrete picture of what operating at the next level actually requires on an ordinary day. Not aspirationally — specifically. What decisions are you making? What conversations are you having? What does a Tuesday look like? The more precisely you can answer those questions, the more the next level functions as something you can move toward rather than a direction you point at. You’re also doing something useful in the process — surfacing the specific things you don’t know yet, which becomes its own form of direction.

Get yourself into the room

The self-concept doesn’t update through thinking. It updates through experience.

Bandura’s work on self-efficacy is unambiguous on this point: the most reliable source of genuine belief in your own capability is mastery experience — doing the thing, or something close enough to it that new evidence registers. Reading about it doesn’t do it. Intending to do it doesn’t do it. The threshold has to be approached.

Which means the method has to include deliberate exposure to the environment you’re trying to enter. Finding proximity to people who are already operating at the next level. Getting into the room, in whatever form that’s available. Taking on smaller versions of the actions that would require the identity to update.

The distinction worth holding onto here is between observation and experience. Watching someone operate at the next level — even repeatedly, even up close — doesn’t produce the same update in the self-concept that doing it yourself does. Proximity creates the conditions. It normalizes the destination, makes it feel less foreign, shows you that the people already there are human and fallible in recognizable ways. But the self-concept only moves when you act, not when you watch. Getting in the room matters. What you do once you’re there matters more.

There’s also something important about which rooms you’re choosing. Swann’s research on self-verification showed that we seek out environments that confirm our existing self-image — it’s an automatic pull, not a conscious decision. Left alone, that pull keeps you in rooms where the current version of you is comfortable and legible. The work is to redirect it deliberately.

What that means in practice is seeking out rooms where the floor is higher than your current ceiling. Not rooms where people already see you as arrived, but rooms where the baseline level of operation is what you’re trying to reach — where you might be the least experienced person present, where you have to stretch just to follow the conversation, where the ambient norm is the thing you’re working toward. That’s uncomfortable. It’s supposed to be. But the self-image that gets shaped in that environment is one that has to expand to belong, rather than one that gets to stay where it is. Do it enough, and what once required a stretch starts to feel like the floor.

Move while it’s uncomfortable, not after

Willpower is the wrong tool for this. If The Lid were a willpower problem, you would have resolved it by now. The mechanisms maintaining it are older and more persistent than conscious intention. You can’t simply decide your way past a system that’s been running in the background for your entire life.

Steven Hayes’ research on psychological flexibility offers a more accurate frame. The goal isn’t to eliminate the discomfort that rises when you approach the threshold — the pull toward retreat, the internal noise, the self-protective signals that Essay 3 described. That response is wired. It fires when you get close to the edge of who you currently are, because that’s exactly what it’s designed to do. Waiting for it to stop before you move is the same as waiting for The Lid to remove itself.

What’s available instead is changing your relationship to the signal. Not suppressing it — interpreting it. The discomfort that fires when you’re approaching the threshold is not evidence that something is wrong. It’s evidence of proximity. That reframe doesn’t make the threshold comfortable. It makes it navigable — which is different, and is enough.

Redesign the environment deliberately

Essay 3 described how the people around you maintain the previous version of you — not out of bad intent, but because their picture of you is built from real history and runs slightly behind. Every time you default to the old identity, even for practical reasons, the new one loses traction. The social environment doesn’t just reflect who you are. It creates conditions that make the familiar version easier to inhabit than the emerging one.

You can’t always exit those relationships. But you can add inputs that run in the other direction.

Deliberately seeking proximity to people who are already operating where you’re trying to go — mentors, peers at the next level, communities where the new version of you is the baseline — isn’t networking as most people understand it. It’s identity scaffolding. You’re borrowing the structure of a self-concept that’s already built while yours is still under construction. That’s not performance. It’s how identity has always developed. The work here is making it intentional.

The thing about accumulation

There’s one more thing I want to say, and it’s the part I find most useful to hold onto when I’m inside the difficulty of this, rather than writing about it at a comfortable distance.

None of this works as a single breakthrough. There isn’t a conversation that cracks it open, a decision that resolves it, a moment where The Lid lifts and stays lifted. What there is instead is accumulation. Each attempt at proximity generates something — a clearer picture of what the next level requires, a small piece of evidence that updates the self-concept, a little less fuzziness on the other side. The layers build on each other in ways that aren’t visible until enough of them are there.

The Lid doesn’t break in a moment. What changes is that enough accumulates on your side of it — enough evidence, enough updated self-concept, enough clarity on the other side — that what was previously impassable becomes something you can move through. The method isn’t a key. It’s a way of building up in the right direction.

One more thing worth saying clearly: there will be another one. Getting through this Lid doesn’t end the game. It opens the next level, which comes with its own threshold, its own version of the gap between who you are and who you’d need to become. That’s not a reason for despair — it’s just the honest shape of the thing. What changes as you move through one is that you get better at recognizing the pattern in the next. The diagnosis becomes faster. The mechanisms are familiar. The accumulation has somewhere to start from. You’re not back at zero. You’re someone who has done this before, which is a different thing entirely.

That’s less dramatic than a breakthrough. I think it’s more true.

Thanks for reading.
—Ryan

Thing to do — Pick one and move

Go back to what you wrote after Essay 1 — the next step you can see but haven’t taken. By now you have more context for what’s actually in the way.

If it’s mostly external — missing information, no map, no proximity — identify one room you need to get into or one person already operating at the next level. Write down the single most direct action that moves you toward that. Not a plan. A next move.

If it’s mostly internal — you know the step, you’ve known it — write down what operating at the next level looks like on a specific, ordinary day. Make it concrete enough that it stops being a direction and starts being a destination. Then do one thing, this week, that puts you in proximity to that picture.

The accumulation starts somewhere. Let it start here.

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

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Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you’re looking to go deeper on the themes from this week’s newsletter, here are a few books that pair well with the conversation:

1. The Surrender Experiment — Michael Singer Singer's memoir is the most direct illustration in print of what it looks like to override the self-protective system this essay describes — consistently, over decades, despite every internal signal telling him to pull back. Less instructional than Living Untethered, more experiential. Worth reading alongside it.

2. Thinking, Fast and Slow — Daniel Kahneman The research backbone for much of what this essay is pointing at. Kahneman's System 1 and System 2 framework is the most accessible explanation of why so much of our self-protective behavior happens before we've made a conscious decision — and why willpower alone is a weak tool against it.

3. The Status Game — Will Storr One of the more underread books on why social identity — how others see us and how we maintain our standing in the groups that matter to us — governs so much of human behavior. Directly relevant to the "how others see you" section and the social maintenance mechanisms the essay describes.

4. Ego Is the Enemy — Ryan Holiday Holiday's argument is essentially that the constructed self — the identity we protect and perform — is often the primary obstacle between us and the work we're actually trying to do. Useful here as a counterweight to the wiring section: the system is real, but it can be worked with.

5. The Art of Impossible — Steven Kotler Kotler's work on peak performance and motivation addresses the gap between knowing what you should do and actually doing it — which is precisely the territory Essay 3 covers. More optimistic in tone than the essay itself, which makes it a good companion read heading into Essay 4.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://ryanroghaar.com

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

There’s a particular frustration that comes after recognition.

You’ve named the pattern. You’ve traced it back through your history and watched it repeat across different contexts, different years, different versions of the same stall. You understand, at least intellectually, what’s been happening and why. And then you wait for that understanding to change something.

Sometimes it does — briefly. There’s a period after recognition where things feel more possible, where the clarity itself generates momentum. But for most people, and across most meaningful thresholds, the Lid doesn’t dissolve just because you’ve seen it. It persists. And the persistence is the part nobody warned you about.

I can say this from experience rather than theory. I’ve been aware of this pattern in my own work for long enough now that awareness clearly isn’t the mechanism for moving through it. Seeing it hasn’t made it go away. Which means the question isn’t just where the Lid comes from — it’s what keeps it in place after you already know it’s there.

The loop

The most important thing to understand about why the Lid persists is that the behaviors maintaining it also prevent the experiences that would challenge it.

It works like this. You approach a threshold — a step that would require you to operate as a slightly different version of yourself. Sometimes what follows is recognizable avoidance: the discomfort of the gap produces hesitation, and the hesitation produces the familiar patterns of deferral we talked about in Essay 1. But sometimes it’s something less dramatic than that. Sometimes you simply don’t know what to do next. The next step isn’t just uncomfortable — it’s unclear. And unclear is its own kind of stuck, one that can look identical to avoidance from the outside while feeling completely different from the inside.

Both versions produce the same result. The specific action that would move you through — the one that would generate new experience, new evidence about what’s actually possible at the next level — doesn’t happen. And because it doesn’t happen, you never find out. The next level stays hypothetical. Something you might be capable of doing, not something you’ve done. What’s more, after recognition the avoidance doesn’t stop — it gets more sophisticated. You know what the threshold looks like, and you produce a convincing amount of activity around it without quite taking it. The substitution feels like progress because it produces real things. It just doesn’t produce the one thing that would actually matter.

The loop closes. Nothing updates. And the longer it runs, the more familiar the stopping point becomes.

It’s nothing personal — you’re wired this way

Before going further, it’s worth saying something that the framing of avoidance and self-protection can obscure: this response isn’t a character flaw; it’s hard-wired. The pull back from the threshold isn’t a defect in the system. It is the system, operating in ways that are deeply ingrained and largely automatic.

The research on self-verification — William Swann’s work in particular — shows that people don’t just passively accept their existing self-concept. They actively seek out information and environments that confirm it, and they resist information that challenges it, often before they’re consciously aware of doing so. This isn’t stubbornness or weakness. It’s a stabilizing function. Identity coherence — knowing who you are and having that confirmed by the world around you — serves real psychological purposes. The system that protects it is running all the time, below the level of deliberate thought.

There’s also a reasonable case that this response runs deeper than habit or learned behavior — that the drive to maintain your position, to stay legible to the people around you, to avoid the social exposure that comes with operating outside your established role, connects to something more fundamental in how humans are wired. Whether or not that’s the full explanation, the practical implication is the same: the pull back from the threshold isn’t always something you’re choosing. It’s something you’re overriding when you push through it. And overriding a deeply wired system requires more than good intentions or intellectual clarity.

Understanding that changes the framing. You’re not failing to do something easy. You’re attempting something that runs counter to a set of responses that have been running in the background for your entire life. That’s worth acknowledging — not as an excuse, but as an accurate description of what you’re actually dealing with.

How others see you

The social dimension of the Lid’s persistence is among the least visible yet most significant.

The people around you — colleagues, collaborators, clients, advisors, even friends and family — carry a version of you that’s based on real history and real experience. That version isn’t wrong, exactly. But it’s retrospective. It reflects who you’ve been, and it shapes what they expect, what they ask of you, and how they represent you to others.

When you start operating differently — reaching toward the next level — that creates friction. Usually not deliberately. More often, the people around you simply respond to the version of you they know, because that’s what they have to work with. A collaborator describes your work in terms that used to be accurate. A client comes to you for what you’ve always provided. An advisor gives you guidance calibrated to who you were when they first got to know you.

I’ve watched this happen in my own work. In trying to build something new with RŌG Health — transitioning from a design and marketing agency into a consultative practice — I noticed that even I occasionally default to the familiar when under pressure. In early conversations with potential clients, I’d find myself leaning back toward the design and marketing framing that I know how to sell, the language that comes naturally, the version of the pitch that has worked before. Not because I’d abandoned the new direction, but because the old one was more practiced, more comfortable, and more legible to the people I was talking to. The new identity was still being built. The old one was ready to go.

That’s the social environment at work. It doesn’t just reflect who you are — it creates conditions that make the familiar version of you easier to inhabit than the new one. And every time you slip back into it, even for practical reasons, the new identity gets a little less traction.

Seeing clearly what’s beyond

There’s one more thing that keeps the Lid in place, and it may be the hardest to name directly.

You don’t fully know what’s on the other side.

The next level — whatever it is for you — isn’t perfectly clear. You can see it directionally. You might even be able to identify the next step. But the actual experience of operating there, what it would feel like day to day, what problems would replace the ones you have now, what would be required of you — that’s all somewhat out of focus. The other side of the barrier isn’t dark. It’s more like looking through something translucent. The shapes are there. The details aren’t.

That fuzziness matters more than it might seem. The pull toward something you can’t fully see is weaker than the pull toward something familiar and concrete. Your current level — with all its frustrations — is at least known. The discomfort there is understood. What’s beyond the Lid is less certain, and certainty, even uncomfortable certainty, tends to win against ambiguous possibility.

What changes this is proximity. The closer you get to the threshold — the more you press against it, even without breaking through — the more the details on the other side begin to come into focus. Each attempt, even an incomplete one, generates something. A clearer sense of what the next level actually requires. A more specific picture of what you’d need to become to operate there. The fog doesn’t lift all at once. But it thins.

Which means the answer isn’t to wait until the picture is clear before you move. It’s to get close enough, consistently enough, that clarity becomes possible. Recognition matters. Understanding where the Lid came from matters. But neither of those things generates the lived experience that actually begins to close the gap between who you are and who you need to become.

That’s what the next essay is about.

Thanks for reading.
—Ryan

Thing to do — Audit the motion

Make a list of everything you’ve worked on in the last two weeks. Then mark each item with one of two labels: things that kept you operating at your current level, and things that would have moved you through to the next one. Look at the ratio. You don’t have to change anything yet. Just see it clearly.

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you’re looking to go deeper on the themes from this week’s newsletter, here are a few books that pair well with the conversation:

1. The Surrender Experiment — Michael Singer Singer's memoir is the most direct illustration in print of what it looks like to override the self-protective system this essay describes — consistently, over decades, despite every internal signal telling him to pull back. Less instructional than Living Untethered, more experiential. Worth reading alongside it.

2. Thinking, Fast and Slow — Daniel Kahneman The research backbone for much of what this essay is pointing at. Kahneman's System 1 and System 2 framework is the most accessible explanation of why so much of our self-protective behavior happens before we've made a conscious decision — and why willpower alone is a weak tool against it.

3. The Status Game — Will Storr One of the more underread books on why social identity — how others see us and how we maintain our standing in the groups that matter to us — governs so much of human behavior. Directly relevant to the "how others see you" section and the social maintenance mechanisms the essay describes.

4. Ego Is the Enemy — Ryan Holiday Holiday's argument is essentially that the constructed self — the identity we protect and perform — is often the primary obstacle between us and the work we're actually trying to do. Useful here as a counterweight to the wiring section: the system is real, but it can be worked with.

5. The Art of Impossible — Steven Kotler Kotler's work on peak performance and motivation addresses the gap between knowing what you should do and actually doing it — which is precisely the territory Essay 3 covers. More optimistic in tone than the essay itself, which makes it a good companion read heading into Essay 4.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://ryanroghaar.com

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

The first essay in this series was about recognition — identifying the pattern, giving it a name, understanding its basic shape. This one is about something harder. If the Lid is real, if it’s consistent, if it shows up across industries and contexts and levels of experience, then the obvious question is: where does it come from?

The short answer is that it gets built. Slowly, quietly, from materials you didn’t choose and experiences you didn’t fully understand at the time. By the time you encounter it as an adult, most of the construction has already been done. You just haven’t had a blueprint to look at.

The ceiling isn’t where you think it is

For most of the time I ran my agency, I wasn’t thinking analytically about why the business grew to a certain point and stopped. I wasn’t sitting with spreadsheets attributing the pattern to market conditions or positioning or timing. I was just working — building, producing, moving from one project to the next. The ceiling wasn’t something I was conscious of fighting. It was just the way things were.

It was only in retrospect, looking back across two decades and then across the subsequent ventures that followed, that the pattern became visible. A revenue level that the business would approach and then drift back from. Setbacks that I’d rebuild from, reliably, to roughly the same place I’d been before. Different circumstances, different years, different structures — same ceiling.

I hadn’t been explaining it to myself. I’d been living inside it without really seeing it at all.

That passive quality — the way the Lid can operate entirely beneath your awareness, not as a problem you’re failing to solve but simply as the texture of your life — is one of the things that makes it so difficult to address. You can’t fight something you haven’t noticed. And most people, for most of the time the Lid is active, haven’t noticed it. They’re just going with the flow of what feels normal.

What makes the pattern significant, once you do see it, is what the research suggests about why it happens. We each carry an internalized picture of who we are, what we’re capable of, and what level of success belongs to us. Maxwell Maltz called it self-image. Psychologists call it self-concept. Whatever the term, the finding is consistent: we tend to perform in ways that confirm the picture we carry — not because we’re consciously limiting ourselves, but because the picture shapes what we attempt, how we interpret difficulty, and when we decide we’ve gone far enough.

The Lid, in this sense, isn’t a ceiling the world put on you. It’s one you’ve been carrying with you all along.

How we learn to see ourselves

Self-concept doesn’t arrive fully formed. It gets assembled — from early feedback, from environment, from the people around you and the messages they send, often without meaning to.

Some of it comes from childhood. Growing up in a household where worry was the default response to uncertainty, where caution was modeled as wisdom — that shapes something. Not dramatically, not in ways that show up as obvious trauma or clear limiting beliefs. More subtly than that. It installs a certain relationship to risk, to the unknown, to what’s reasonable to expect. You don’t notice it as a lesson. You absorb it as reality.

Some of it comes from early success — which is a less obvious source than failure, but just as significant. When you develop genuine competence in a particular domain, that competence becomes part of your identity. You are someone who does this well. The problem is that identity, once formed, tends to protect itself. Psychologist William Swann’s research on self-verification shows that people actively seek out information and situations that confirm their existing self-view — even when that self-view is limiting. The zone of competence becomes the zone of comfort, and the zone of comfort becomes the outer boundary of what feels reasonable to attempt.

E. Tory Higgins, whose work on self-discrepancy is some of the most useful in this space, identified something important: we each carry multiple versions of ourselves simultaneously. There’s the self we actually are, the self we want to become, and the self we feel we ought to be. When the gap between these versions becomes too great — when the next step would require acting as a self that feels too far from the one we know — the discomfort that gap generates tends to push us back toward familiar territory. Not in a conscious, deliberate way. More like a gravitational pull.

Hazel Markus and Paula Nurius described this dynamic through what they called possible selves — the mental images we hold of who we might become. The research shows that these possible selves function as a kind of cognitive template: they shape what we notice, what we pursue, what we believe is available to us. If your image of the next version of you is vague or feels disconnected from who you are now, the pull toward it weakens. The gap becomes harder to cross, not because the destination is too far, but because it’s too unclear.

The Lid forms at exactly that gap.

A pattern on the move

Here’s what makes this particularly difficult to see: the Lid moves with you.

You change industries. You start something new. You leave the environment where you first hit the barrier and enter a completely different one. And after an initial period of momentum — the early stage where everything feels open and progress is visible — you find yourself back at the same threshold. Different context, same wall.

This isn’t bad luck. It’s the self-concept doing its job.

The picture you carry of who you are and what you’re capable of doesn’t stay behind when you change circumstances. It comes with you. And it will reproduce the same ceiling in the new environment, not because you’re failing, but because the internal architecture hasn’t changed. You’ve moved the business, but not the builder.

Across nearly five hundred conversations on my podcast with people who have built things — companies, careers, creative practices — I’ve watched this pattern repeat in forms I couldn’t have predicted. No two paths look alike. But the structure of the stall is remarkably consistent. People rise to the level their self-concept allows, and then they stop — not because the environment stopped them, but because they’ve reached the outer edge of who they believe themselves to be.

It’s also environmental

It’s worth being clear about the external piece here, because the Lid isn’t purely internal and it would be dishonest to suggest otherwise.

The environment you work in has real effects on where the ceiling gets set and how easy it becomes to approach it. When I worked inside an agency — with a team, with structure, with the daily friction of other people’s thinking pushing against my own — I moved faster and further than I did working alone. I was promoted quickly. I grew into roles I wouldn’t have sought on my own.

Working largely in isolation, as I have for most of my career, creates a different kind of ceiling. Not because solo work isn’t productive — it can be intensely productive — but because certain kinds of growth require proximity to people who are already operating at the level you’re trying to reach. You need exposure to how things actually work at the next level. You need feedback that comes from being in the room, not just from reading about it. You need, sometimes, someone who has already crossed that threshold to show you what the other side looks like.

The research on self-efficacy — Bandura’s work, which remains foundational — makes clear that one of the most reliable sources of genuine belief in your own capability is what he called mastery experiences: actually doing the thing, at the level required, and surviving it. Without sufficient exposure to the environment you’re trying to enter, those mastery experiences are hard to accumulate. The external face of the Lid — the map problem we talked about in Essay 1 — and the internal face reinforce each other. Isolation maintains both.

The part that’s hardest to admit

There’s something else that happens over time, and it may be the most important piece of this. At some point, if the Lid persists long enough, you stop experiencing it as a barrier. You start experiencing it as yourself.

The ceiling becomes invisible not because it disappears, but because you’ve adjusted to its presence. You’ve learned, without deciding to, what level of effort produces a comfortable result. You’ve found the altitude where things don’t hurt too badly — where there’s enough of what you need, enough freedom, enough forward motion — and you’ve settled into it. Not as a conscious choice. More like how a room eventually feels like the right temperature.

This settling can last for years without being recognized as just that, settling. The explanations stay current — there’s always a reason why now isn’t quite the right time, why this particular moment requires patience, why the next step needs a little more preparation. The Lid doesn’t announce its presence. It just becomes a part of you. And then, at some point, something happens that makes it impossible to look away.

When most people finally reckon with the Lid, it doesn’t happen as a calm moment of reflection. It happens in the middle of something hard. A business that isn’t growing the way it should be. A career that stalled somewhere along the way. A financial situation that’s impossible to ignore anymore. The feeling isn’t “I see the pattern now.” It’s closer to: why am I here, and how did I let this happen?

That’s the disorienting part. The problem in front of you feels immediate — because it is immediate — but its roots are years old. You’re dealing with the present consequence of something that was quietly accumulating the whole time. And that gap between what you’re feeling now and how long it’s actually been building tends to produce one of two responses. Some people move into regret and self-recrimination — cataloging the decisions they should have made differently, the time they wasted, the opportunities they missed. That response is understandable, but it isn’t useful. It keeps you anchored to the history rather than oriented toward what comes next.

The more productive response — and the harder one — is to use the moment as the thing that finally makes the pattern visible. Not to feel good about where you are, but to see clearly how you got here, which is the only way to stop repeating it.

Understanding where the Lid came from doesn’t make it disappear. But it changes what you’re actually dealing with — from a vague, personal sense of failure to something more specific, more structural, and more addressable.

That distinction matters more than it might seem. Because the next essay is about something most people don’t expect: why seeing the Lid clearly isn’t enough to move through it — and what keeps it in place even after you’ve recognized it for what it is.

Thanks for reading.
—Ryan

Thing to do — Go one level deeper

Take the explanation you wrote down after Essay 1 — the one you’ve been giving yourself for why you haven’t taken the next step. Now ask a different question: where did that explanation come from? When did you first start believing it? Who or what taught you that this was the reasonable limit? You don’t have to answer completely. Just start looking at the explanation itself, not just what it’s explaining.

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you’re looking to go deeper on the themes from this week’s newsletter, here are a few books that pair well with the conversation:

1. Psycho-Cybernetics — Maxwell Maltz The book Bob Burg reached for first when this conversation came up. Maltz, a plastic surgeon, noticed that changing a patient’s appearance didn’t always change how they saw themselves — and built a framework around that observation. The foundational text on how self-image shapes and limits performance, and the clearest early articulation of what we’re calling The Lid.

2. The Big Leap — Gay Hendricks Hendricks makes a compelling case that most people have an unconscious "upper limit" — a ceiling on how much success, happiness, or forward momentum they'll allow themselves before they self-sabotage back to familiar territory. It maps directly onto the comfort ceiling we explored this week, and it's one of the more accessible books on why success can reinforce the Lid as much as failure can.

3. Mindset — Carol Dweck The research behind growth mindset is referenced in Essay 1, and Dweck’s book is where that work lives in its most accessible form. Read it not as a solution to The Lid but as one useful lens among several — which is exactly how the essay frames it.

4. The Untethered Soul — Michael Singer Recommended by Bob Burg in the conversation that started this project, and worth reading before Living Untethered if you haven't encountered Singer's work before. At its core it's about learning to observe the internal voice that defines and defends your sense of self — which is precisely the mechanism Essay 2 is describing.

5. Triggers — Marshall Goldsmith Goldsmith's book is about the environmental and behavioral cues that pull us back to old patterns regardless of our intentions. It's the most practical treatment on this list of the external face of the Lid — how the environments we operate in shape and maintain the ceiling, often without our awareness.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://ryanroghaar.com

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.

Over the next month in The Path, we're beginning a new four-part series — a natural extension of the work we started with The Mindset Movement. Where that series explored how the mind shapes what's possible, this one goes after something more specific: the invisible barrier that appears when growth starts to outpace who we believe ourselves to be. We're calling it The Lid. Each essay builds on the last, and the whole thing is designed to leave you with a clearer picture of something you've almost certainly already felt before. Let's dig in.

For most of my career, I’ve been able to move by doing what I know how to do. I build things. I ship things. I create, produce, and put work into the world consistently, across more projects than I can easily count. That part has never been the problem.

The problem is what happens at a certain point in every one of those projects — a point that arrives reliably, regardless of the industry, the idea, or how much momentum I’ve managed to build. Things are going well. The early work is done. Progress is visible and earned. And then, almost without announcement, the next step becomes something I can see clearly but can’t seem to actually take.

It’s not that I stop working. I keep going. I refine and optimize and improve what already exists. But the specific move that would change the shape of what I’m doing — the one that would push the whole thing to the next level — never happens. And I’ve spent a lot of time trying to understand why.

I’ve attributed it to fear. To missing information. To not knowing the right people. To unclear direction. To having the wrong guidance, or no guidance. Whatever! Each explanation felt true enough at the time, but none of them held up across every instance where I ran into the same wall, in completely different contexts, doing completely different work.

In July of 2025, I was talking about this phenomenon for the millionth time on my podcast, Eggs! The Podcast, with business legend Bob Burg, co-author of the wildly popular book, The Go-Giver. I brought up the problem the way I usually do — trying to describe this thing I could feel but hadn’t been able to articulate precisely. Burg didn’t need much context. He recognized it immediately, and the first thing he did was reach for a book he’d read in 1983 — Psycho-Cybernetics by Maxwell Maltz — because it was where he’d first begun to understand how unconscious belief limits performance. We can never attain more than our most limiting belief, Maltz argued. And when we find ourselves repeatedly hitting the same ceiling, that’s the mechanism at work. Burg referred to it as a set point — an unconscious definition of who you are and what level of success belongs to you. And then he said something that’s stayed with me: it’s an emotional lid. One we place on ourselves without knowing we’ve done it. That’s what makes it so effective — and so hard to see.

That conversation was the beginning of the research behind this project. The experience it was pointing to, though, is one I suspect most people reading this are familiar with.

What we’re actually dealing with

There’s a particular kind of stuck that doesn’t look like stuck from the outside. You’re still active. Still producing. Still making decisions and completing tasks, showing up for the work. But there’s a specific step — one you can usually describe out loud — that you keep not taking. And the longer that goes on, the more elaborate your reasons for not taking it become.

This is The Lid.

The Lid is the invisible barrier that appears when growth outpaces identity. It’s not a skill gap, though it often disguises itself as one. It’s not a motivation problem, though it can look like one, too. It’s the convergence of several things happening at once: the gap between who you are and who you’d need to be to take the next step; the discomfort of acting in ways that don’t yet feel natural or earned; the quiet, persistent doubt about whether you can actually bridge that gap; and the behaviors that emerge — mostly unconsciously — to protect you from having to find out.

Everyone arrives at The Lid through their own zone of competence. A contractor who has mastered their craft but won’t take on larger projects. A teacher who knows exactly how to run a classroom but sidesteps leadership. A founder who can build a product but stalls when it’s time to sell it. The specifics differ, but the structure of the moment is the same. You’ve gone as far as you can go doing what you already know how to do, and the next step requires operating in territory where your current sense of yourself doesn’t quite apply.

That’s the condition The Lid creates. And it produces a feeling that’s surprisingly hard to put words to: you can see the path forward, but it lies just beyond an invisible wall.

The two faces of The Lid

What makes The Lid difficult to diagnose is that it operates on two levels, and most of us have only been taught to look at one.

The internal face is the familiar one — mindset, confidence, identity, belief. It’s where self-doubt lives, where old stories about what’s possible for you take up residence, where the sense that the next step doesn’t quite fit who you are quietly does its work. There’s real signal in all of that. The way you see yourself does shape what you’ll attempt, and whether you’ll persist once things get hard.

But the internal face is only half the picture.

The external face of The Lid is structural. At the next level, the work looks different. The decisions are different. The people, the feedback loops, the unwritten rules of how things operate — all of it changes. And if you haven’t had exposure to that level yet, you’re not just dealing with doubt. You’re dealing with a genuine absence of information about how to move. That’s not a mindset problem. It’s a map problem. And when it gets misread as purely internal — when you treat a missing map as a confidence issue — you end up working on the wrong thing entirely.

The Lid lives in the interaction between these two faces. Internal uncertainty and external ambiguity reinforce each other in a cycle that can run for a long time before it’s seen clearly. You hesitate because you don’t know exactly what to do next. The hesitation gets interpreted as doubt about your ability. The doubt makes you more sensitive to risk. Increased sensitivity to risk makes you more likely to avoid the situations that would give you the information you actually need. The cycle closes, and you stay in place — not because you can’t move forward, but because the system is working exactly as designed.

Self-handicapping

Inside that cycle, something specific happens that’s worth understanding directly.

You introduce friction. Not intentionally, and not in ways that look like sabotage from the outside — but in ways that consistently create just enough distance between you and the step you’re looking for. You decide you need more information before you’re ready. You wait for conditions that feel more certain. You shift energy toward tasks that feel productive but don’t require you to cross the boundary you’re approaching.

Each of those decisions is defensible. Taken individually, they make sense. Taken together over time, they form a system — one organized around a single, unspoken goal: avoiding the moment where you’d have to find out whether you can actually do the thing.

Psychologists call this self-handicapping. It’s the tendency to create or emphasize obstacles so that if things don’t go well, the outcome can be explained by the obstacle rather than by your capability. It sounds harsher than it is. This isn’t about laziness or lack of ambition. It’s a protective mechanism, and a sophisticated one. It keeps the question — can I actually do this at the level required? — from ever requiring a definitive answer. If you never fully commit, you never fully expose the gap.

That’s what makes The Lid persistent. It doesn’t require you to believe anything that’s obviously false. It only requires you to accept explanations that are partially true and stop there. And the partial explanations are always available, always plausible, always easy to reach for. “I need more time.” “I’m not quite ready.” “The conditions aren’t right yet.” Each one contains a piece of truth. Together, they become a holding pattern.

Mindset work can help at the margins, but it doesn’t resolve this on its own. The research on growth mindset shows real effects — but modest ones. Changing how you think about your potential doesn’t automatically close an identity gap, and it doesn’t generate the missing external information that’s often part of what’s keeping you in place. People can genuinely believe in their own capacity for growth and still find themselves running the same pattern, because belief alone doesn’t address the full structure of what’s happening.

What it actually means

Here’s the reframe that sits at the center of this project:

The Lid is not evidence that you’re incapable. It’s evidence that you’re close.

If you were far from the next level, the step in front of you would feel irrelevant or obviously out of reach. You wouldn’t be circling it. You wouldn’t be able to describe it with any precision. The fact that you can see it clearly — that you can feel the pull toward it and the resistance against it simultaneously — means you’re already at the edge of something that would require a different version of you to inhabit.

That version exists. It’s just not yet stable. And the gap between where you are and where that version lives is exactly what creates the friction.

Once you can see the pattern this way, the experience shifts — not dramatically, but meaningfully. The hesitation stops feeling like a personal flaw and starts feeling like a recognizable signal. You begin to catch yourself introducing friction, and to distinguish between an explanation that reflects a real gap and one that’s functioning as protection. The right question stops being what do I need to fix before I can move? and starts being what, specifically, is creating this gap — and how much of it is internal, how much is external, and how are the two reinforcing each other?

That precision is what makes movement possible. Not by removing the discomfort, but by pointing your attention at the actual mechanism instead of the story you’ve been telling yourself about it.

The next essay in this series goes one level deeper — into where the Lid comes from in the first place, and why the same pattern tends to repeat across such different areas of life. Understanding what creates it changes what you’re able to do about it.

Thanks for reading.
—Ryan

Thing to do — Start here

Write down the next step you can clearly see but haven’t taken. Then write down every explanation you’ve given yourself for why not. For each one, ask honestly — is this pointing to a real gap, or is it protecting an identity that hasn’t caught up yet?

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

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Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you’re looking to go deeper on the themes from this week’s newsletter, here are a few books that pair well with the conversation:

1. Psycho-Cybernetics — Maxwell Maltz The book Bob Burg reached for first when this conversation came up. Maltz, a plastic surgeon, noticed that changing a patient’s appearance didn’t always change how they saw themselves — and built a framework around that observation. The foundational text on how self-image shapes and limits performance, and the clearest early articulation of what we’re calling The Lid.

2. The Go-Giver — Bob Burg & John David Mann The book that brought Burg into this conversation in the first place. Less about the Lid directly and more about the belief systems and relational dynamics that either accelerate or constrain growth. Worth reading alongside Psycho-Cybernetics.

3. Mindset — Carol Dweck The research behind growth mindset is referenced in Essay 1, and Dweck’s book is where that work lives in its most accessible form. Read it not as a solution to The Lid but as one useful lens among several — which is exactly how the essay frames it.

4. The Millions Within — David Neagle Recommended by Burg in the same conversation. Neagle’s own story is one of breaking through a set point that had defined his ceiling for years. Practical and direct, and specifically focused on the kind of internal barrier the essay describes.

5. Living Untethered — Michael Singer Also recommended by Burg, who called it the most important personal development book he’d ever read. Where the other books on this list address the mechanics of the Lid, Singer goes deeper — into the internal observer that creates and maintains the stories keeping you in place. Third in a series, after The Untethered Soul and The Surrender Experiment, but stands on its own.

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Many people don’t realize they’re part of something until they’re already in the middle of it.

Think about what it means to be a fan of a team. You show up because you care. So does the person next to you, and the person next to them. Everyone is there for their own reasons, with their own history with the team, their own stake in the outcome. Nobody coordinated it. But put enough of those people in the same room and something larger emerges — shared context, shared investment, a common cause that nobody had to organize because everyone already believed in it. The team is on the field doing the work. The fans are just being fans. And somehow, together, they’ve built something bigger than either could have built alone.

Business communities are no different, and last week in Salt Lake City, I got to watch it happen in real time.

I had the chance to attend BioHive Week, a collection of life sciences events organized by BioHive — one of the primary organizations bringing together Utah’s life sciences and healthcare innovation community. Medical devices, diagnostics, biotech, research institutions, the companies that support them — over the course of the week, that entire ecosystem gets pulled into the same orbit through a mix of events spanning early-stage ideas all the way up to established players.

What stood out wasn’t any single event, but how consistent the environment felt across all of them.

You could move from a social setting to a pitch event to a room full of executives and see the same basic behavior. People were willing to engage. They made introductions. They pointed each other in useful directions. Not in a forced way, and not as some coordinated effort. It just seemed to be how things worked.

That matters because everyone is still doing their own work. Every company is trying to build, raise capital, ship product, solve its own problems. There’s no shared outcome everyone is directly tied to. And yet there’s a clear sense that the system itself has value — and that contributing to it, when the opportunity is there, is just part of how you operate.

In a space like life sciences, that kind of environment has real consequences. The work is slow, complicated, and expensive. You don’t move quickly through regulatory pathways or clinical validation. You don’t shortcut your way into trust with providers or patients. So the ability to learn from someone who’s a few steps ahead, or to get pointed in the right direction without losing months figuring it out yourself, matters more than it would somewhere else.

Over time, those small interactions add up. The next company doesn’t start from scratch. The next founder has better access than the last one did. The next decision gets made with a little more context behind it. Nobody planned it that way. Nobody sat down and designed a system for transferring knowledge and opening doors. It’s what happens when enough people are doing hard things in the same place for long enough — they start to recognize each other, trust each other, and operate like they’re part of something larger, even if nobody ever says it out loud.

And once that shift happens, it compounds.

Utah’s life sciences sector has quietly become one of the fastest-growing hubs in the country, and when you’re standing inside the community watching how people actually behave with each other, the growth stops feeling like a coincidence. It starts looking like the inevitable result of how these people choose to operate.

When I launched RŌG Health, our medtech commercialization advisory, earlier this year, we weren’t sure what kind of reception we’d get stepping into a space we were somewhat new to. What we found was that the door wasn’t closed by default. Conversations weren’t hard to get into. People pointed us somewhere useful more often than not. That’s not something you can assume in every market, and it’s not something that happens by accident in this one.

Utah’s life sciences ecosystem is earning a lot of attention right now, and most of that conversation is about growth — more companies, more capital, more visibility. That’s all real. But underneath it, and probably more important, is how people are choosing to operate while that growth is happening. BioHive is clearly playing a role in creating the conditions for it. The strength of it, though, comes from how individuals show up once they’re there — and the fact that enough of them keep showing up the same way.

Everyone is still responsible for their own outcome. But whether they realize it or not, they’re building in the same direction — together.

That distinction — between a market and a community — might be the clearest explanation for how this ecosystem got where it is. And if the behavior holds, it’s probably where it’s going.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

More to explore

• Biohive Utah – Building, branding, and bringing together Utah’s life sciences and healthcare innovation community

• Biohive Week – Utah’s annual celebration of life sciences and healthcare innovation, combining flagship events BioHive Live and the Best of BioHive Awards Gala with week-long community and partner-led programming.

• Andrew Robertson – Executive director, BioHive Utah

  Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
  
  Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

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RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://ryanroghaar.com

Eggs! The Podcast - https://www.eggscast.com

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Most people say they want growth when what they really want is relief. They want the business to get easier. They want the uncertainty to settle down. They want one smart move, one good quarter, one clear signal that the hard part is behind them. That’s understandable. It’s also not how this works. The pressure doesn’t go away. It just changes form.

That’s part of why I’ve grown skeptical of how often innovation gets framed as the answer. We treat progress like it belongs to whoever comes up with the freshest idea or the boldest pivot. But most businesses aren’t stuck because they lack imagination. They’re stuck because what they claim to be and what they consistently deliver don’t quite line up. The message drifts. The execution slips. Things that used to work stop working, and no one wants to slow down long enough to figure out why.

Iteration doesn’t get much attention because it sounds smaller than innovation. It feels like settling. In reality, it’s the opposite. It’s the willingness to stay with something long enough to make it sharper, clearer, more reliable. Not by overhauling everything at once, but by tightening what’s already there and being honest about what isn’t holding up. It rarely looks like progress from the outside, but it's usually where the real leverage is.

That tension is only getting more pronounced. Tools like AI make it easy to produce — faster, cheaper, and in higher volume than ever before. That’s useful, up to a point. But output on its own doesn’t solve much. If anything, it raises the bar on judgment. The teams that benefit from this moment won’t be the ones pushing the most into the world. They’ll be the ones paying close attention to what actually lands and adjusting accordingly.

Where things tend to break down is in the middle. Founders get caught between what they’ve already built and what they think they should be building next. They stay busy, but the work starts to scatter. One week it’s a new angle, the next week it’s a new channel, then a new offer. None of it gets enough time to prove itself, so nothing really sticks. It creates the feeling of effort without much forward movement.

In our recent conversation with Eggs! The Podcast guest and CEO at Afterburner, Chris Boucousis, is how little patience he has for that kind of drift. He talks about iteration as a structured way of operating, not a vague idea about improvement. His background as a fighter pilot shapes that perspective — when things are moving quickly, you don’t have the luxury of guessing your way through decisions. You need a clear destination, an honest read on where you are, and a way to close the gap. Then you do it again. Strip away all the noise around entrepreneurship, and that’s still one of the more dependable ways to make progress. Chris has spent years applying that thinking in business, and it comes through clearly in his approach to growth.

What High Performers Do Differently

Chris Boucousis didn’t come up through the usual business channels. He started in a cockpit. He spent over a decade in the Australian Air Force flying high-performance fighter jets, where hesitation isn’t just costly — it’s fatal. That environment leaves no room for vague goals or half-formed plans. You define the mission, assess reality, and act with precision.

When an autoimmune disease cut his flying career short at 30, Boucousis was forced into an abrupt transition — one that ultimately led him into entrepreneurship. His first venture, launched in Afghanistan in the mid-2000s, scaled rapidly amid chaotic conditions, growing into a multi-thousand-person operation that managed complex logistics and infrastructure projects. It wasn’t polished. It wasn’t predictable. But it reinforced something he had already learned as a pilot: progress comes from constant adjustment, not perfect planning.

Today, as CEO of Afterburner, Boucousis works with organizations around the world to apply that same mindset to business. His focus is straightforward — help leaders operate with more clarity, move faster without losing discipline, and build systems that improve over time instead of breaking under pressure. What he brings isn’t theory. It’s a repeatable way of thinking, forged in environments where getting it wrong wasn’t an option.

The Mechanics of Momentum

If innovation gets the spotlight, iteration does most of the real work. Chris kept coming back to a point that a lot of founders need to hear: growth is usually less about finding the brilliant next idea and more about improving what’s already in motion. These were a few of the sharpest moments from the conversation.

“You’ve got to be focused on where you’re going… and really honest about where you are. Then you have to keep trying something new.”

Actionable insight: Most businesses don’t need more ambition; they need a tighter loop between target, reality, and response. If you’re clear on the destination but fuzzy on your current position, you’re not iterating — you’re guessing.

“Take something and make it a little better tomorrow… then take that and make it a little better again the next day.”

Actionable insight: It sounds simple, which is exactly why it gets overlooked. But steady improvement, applied consistently, is still one of the few advantages that compounds over time.

“Every time I tried to hustle, it went bad. Every time I stuck to the basics, it went well.”

Actionable insight: A lot of effort gets wasted chasing momentum instead of building it. The better move is usually quieter — refine what already works before reaching for something new.

“People don’t actually want constant change… they want consistency. They want to know that if they buy something, it’s what you say it is.”

Actionable insight: This is where many brands lose ground. Reinvention feels productive internally, but externally it can look like instability. Consistency builds trust faster than novelty.

“We tend toward doing things… not achieving things.”

Actionable insight: Activity is easy to justify, especially when you’re busy. But if the work isn’t tied to a clear outcome, it’s just motion — and motion doesn’t scale.

“If it feels like the work isn’t going anywhere… it probably isn’t.”

Actionable insight: That instinct is usually right. The challenge is acting on it early enough to redirect your effort toward something that actually moves the business forward

“Best known is better than best.”

Actionable insight: Perfection is a poor strategy if no one sees the product. Visibility, clarity, and feedback will do more for growth than another round of internal improvements.

Staying in the Loop

There’s a version of this conversation that turns into motivation. Work harder. Stay disciplined. Keep going. That’s not really the point. Most people already know they need to do those things. The gap is usually somewhere else. It’s in how the work is structured. It’s in whether there’s a real feedback loop, or just a constant stream of activity that never quite gets examined.

Iteration, done properly, forces that examination. It asks you to define what you’re actually trying to achieve, measure where you stand, and make a decision about what changes next. Not everything at once. Just the next move. That sounds simple, but it requires a level of honesty that many businesses avoid. It’s easier to stay busy than it is to admit something isn’t working and adjust it in real time.

The advantage, if you’re willing to operate this way, is that progress becomes a lot less mysterious. You stop waiting for the breakthrough and start building momentum on purpose. It may not look dramatic from the outside, but over time, it’s the difference between a business that stalls and one that builds on itself over time.

Thanks for reading.
—Ryan

If you’re ready for life to feel more intentional, more aligned, and more within your control, this guide gives you the structure to make that shift real. Your next version starts with a single decision. Get the field guide

The Path is sponsored by: Taelor Style

A better way to dress for men on the go

Taelor is a subscription menswear service built for professionals and men on the go. Using AI and real stylists, Taelor curates outfits that fit your lifestyle—no shopping, no laundry, no decision fatigue. If you want to look sharp without spending mental energy on it, use code PATH at checkout for 25% off your first order.

Get Started

Ready for more?

Catch Nick Avaria’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective:

1. Atomic Habits — James Clear
   Clear’s core idea is simple: small improvements, applied consistently, outperform big, sporadic changes. It’s probably the most accessible entry point into understanding why iteration works—and why most people abandon it too early.

2. The Lean Startup — Eric Ries
   This is the closest thing to a formal framework for what Chris is describing. Build, measure, learn. Not glamorous, but highly effective when actually followed instead of just referenced.

3. The Checklist Manifesto — Atul Gawande
   A great reminder that consistency beats brilliance in high-stakes environments. Surgeons, pilots, and operators rely on repeatable systems—not inspiration—to get things right.

4. Deep Work — Cal Newport
   If iteration is the strategy, focus is the requirement. Newport makes a strong case that the ability to concentrate without distraction is becoming one of the most valuable skills in modern work.

5. Good Strategy/Bad Strategy — Richard Rumelt
   This one helps separate real progress from noise. Rumelt breaks down what effective strategy actually looks like—and why most organizations avoid it in favor of vague ambition.

More to explore

• Afterburner Inc — Chris Boucousis’ firm bringing fighter pilot frameworks into business

• Flawless Leadership — His latest thinking on execution, leadership, and performance

• Chris Boucousis — More from Chris on leadership and iteration principles

  
  Would you like a personal introduction to this or any of the incredible leaders featured in The Path Weekly to explore business or other collaborative opportunities?
  Contact me here to learn more about my B2B matchmaking service.

Want to put your brand in front of 13,000+ business and technology leaders each week? Contact me to learn more about sponsorship opportunities.

Work with me

RŌG Health - A commercial readiness and strategy firm for medtech companies, helping CEOs identify what’s blocking growth and make clear, de-risked decisions around commercialization, partnerships, and fundraising.
https://roghealth.com

Ryan Roghaar - Artist/Creative Director/Author
https://ryanroghaar.com

Eggs! The Podcast - https://www.eggscast.com

Get featured

Do you want to be featured in a future edition of The Path Weekly?
Contact me to learn more.