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?
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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

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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. 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

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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

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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

• 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?
  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://rogha.ar

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

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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

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

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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. 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

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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.

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

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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

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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?
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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.

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 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.

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

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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.

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.

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.

There was a time — not so long ago — when the internet rewarded volume more than judgment. Publish more. Post more. Chase more keywords. Feed the beast with enough content and eventually something would break through. That game isn’t dead, exactly, but it’s getting less compelling by the minute. What’s replacing it is smaller, narrower, and in a lot of cases more profitable: people turning hard-earned expertise into businesses of their own.

The shift we’re talking about is important because the economics have changed entirely. Generic information is cheap now — in most cases it’s effectively free. AI can summarize, remix, and regurgitate it in seconds. But organized expertise is another thing entirely. Knowing what matters, what doesn’t, what order it goes in is key, but most importantly where people get tripped up, what actually works in practice, and what sounds good but fails in the field — that is where the real value is. Maybe more than it used to be. The market is getting flooded with answers, but the one thing AI cant yet replicate is life experience.

That’s part of why GEO has my attention in particular. Search is no longer just about blue links and ranked pages. More and more, the interface is becoming the answer itself. Google’s AI Overviews now reach more than 2 billion monthly users, and OpenAI says ChatGPT has more than 900 million weekly active users. If that’s where discovery is heading, then the businesses with an edge won’t just be the ones producing the most content. They’ll be the ones creating material that is clear enough to be surfaced, specific enough to be trusted, and useful enough to be cited. That’s a different discipline entirely. Less shouting, more substance.

The opportunity, then, is not “create a course” in the flimsy internet-marketer sense of the phrase. It’s to build an expertise business around a real problem, for a real buyer, with real stakes attached. That might be continuing education, advisory work, a niche training product, a paid workshop, a tight subscription, or a body of intellectual property that solves one expensive problem really well. The point is not to teach everything to everyone, the point is to know something specific well enough that the right people will pay to save time, avoid mistakes, or move more quickly.

And this is where a lot of people miss the plot. They assume the value is in protecting the secret. Usually it isn’t. The value is in the packaging, the point of view, the structure. In being able to say, “Here’s the problem, here’s the order of operations, here’s what matters, here’s what to ignore, and here’s why.” That’s what people buy. Not just information, but compression. Not just access, but clarity. In an AI-heavy market, that difference starts to matter even more. Machines can generate language, but they still can’t manufacture real-world perspective.

Few people explain that better than Eggs! The Podcast guest and founder at ProCourseStart, Justin Allan Montgomery, a former nurse practitioner who turned specialized operational knowledge into a serious education business by solving a very specific problem for a very specific audience. What he built is a useful case study in where things are headed: not toward bigger audiences for the sake of ego, but toward tighter positioning, clearer value, and businesses built on expertise people can actually use.

From Clinical Practice to Scalable Expertise

Justin Allan Montgomery didn’t come to this conversation from the usual creator-economy angle. He came to it through work that carried real stakes. After earning his master’s degree and becoming a nurse practitioner, he built a career in healthcare, eventually launching his own medical practices in areas including men’s health and telemedicine. Along the way, he ran into a familiar ceiling: a strong income, yes, but one still tied to hours, shifts, and the limits of a professional schedule. That tension pushed him toward ownership. He built clinics, scaled them, and later sold them.

What changed his trajectory more dramatically was the realization that the business he had built could become a blueprint for others. What began as a blog and a series of one-on-one consultations eventually became an education company built around a highly specific need: helping medical professionals start practices of their own. He took operational knowledge earned in the field, packaged it into structured training, and discovered there was real demand for clarity in a niche market. His first course generated $50,000 in seven days. A few years later, that education business had grown into an eight-figure asset.

That background is what makes Montgomery worth listening to here. He isn’t theorizing about expertise as a business model from a distance. He built one by focusing on a narrow audience, solving an expensive problem, and resisting the urge to overcomplicate the thing. His perspective is practical, sometimes blunt, and grounded in the economics of what actually sells: not endless information, but organized experience delivered in a way people can use.

What Real Expertise Businesses Get Right

If the internet is shifting from broad content to credible, organized expertise, the mechanics matter. Montgomery’s best points weren’t really about “courses” at all — they were about demand, positioning, packaging, and the discipline to solve an actual problem instead of just publishing more noise.

“Everyone is an expert in something.”

Actionable insight: Most people don’t have an expertise problem. They have a framing problem. The work is not inventing something from scratch; it’s identifying which part of what you already know solves a costly, annoying, or time-sensitive problem for a specific group of people.

“That’s what people were asking for. And so I just kind of create it and deliver the demand.”

Actionable insight: This is a good reminder that demand often shows up before the business model does. If people keep asking the same questions, booking the same consult, or looking for the same shortcut, there’s a decent chance the market is already telling you what the offer should be.

“You do not need tens of thousands, hundreds of thousands of customers… you need a few hundred to a thousand.”

Actionable insight: Broad appeal is overrated. A lot of smart businesses get built once someone stops chasing mass attention and starts focusing on a smaller group with a sharper need. Better economics usually come from relevance, not reach.

“You need to identify the problem first within a specific group of people, and then do your knowledge and skills translate into a solution.”

Actionable insight: This is where many offers fall apart. Being knowledgeable is not enough. The real question is whether your expertise removes friction, creates opportunity, saves time, or helps someone avoid an expensive mistake. If it doesn’t, the market will treat it like trivia.

“One great way to get found on ChatGPT or Gemini is to have a frequently asked question section… and key takeaways.”

Actionable insight: GEO gets practical very quickly. If discovery is moving toward synthesized answers, then clear structure matters. Write the way people search. Answer the obvious questions directly. Make your content easy for both humans and machines to retrieve, understand, and cite.

“If you want this business model to work, you have to deliver free valuable information… it’s not optional.”

Actionable insight: The smartest expertise businesses don’t hoard knowledge; they publish enough of it to establish trust. The trick is not giving away nothing. It’s giving away enough signal that the right buyer can tell you actually know what you’re doing.

“People are willing to spend a couple hundred bucks to be told exactly what to do from an expert who has experience with it versus just finding a bunch of random pieces online and putting it together themselves.”

Actionable insight: People rarely pay for information alone. They pay for compression. They pay for sequence. They pay for someone to eliminate wandering and hand them a cleaner path from problem to outcome.

“You need to look at this as not just building a course. You got to look at this as building a course business.”

Actionable insight: That distinction matters. Too many people obsess over the product and ignore the structure around it — the positioning, the content engine, the distribution, the promise, the audience. A good asset without a business model around it is just a well-made file.

“As long as you’re solving the problem, it doesn’t have to be perfect.”

Actionable insight: Perfection is one of the easiest ways to delay a viable offer. If the thing works, if the promise is clear, and if the user can get the result, you’re usually better off launching and refining than endlessly polishing a version no one has paid for yet.

Where This Goes Next

There’s a temptation, especially right now, to believe the market has become too crowded to break through. Too much content. Too many creators. Too many tools making it easier for everyone to say roughly the same thing. But that’s exactly why specificity matters more than it used to. The businesses with staying power won’t be the ones trying to appeal to everybody at once. They’ll be the ones that know precisely who they’re for, what problem they solve, and how to deliver that solution with enough clarity that trust can form quickly.

That’s what makes expertise such a durable raw material. It isn’t just knowledge. It’s knowledge shaped by consequence. Trial and error. Repetition. Context. A real point of view forged under real conditions. That kind of experience can be packaged, taught, and scaled, but it can’t be faked very easily. Not by a prompt, not by a content factory, and not by someone who has only studied the surface of the thing.

The more AI fills the internet with answers, the more valuable it may become to build something rooted in lived perspective. Not bigger for the sake of being bigger. Better aimed. Better structured. More useful. That, to me, is the real opportunity in front of a lot of smart operators right now.

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. The 1,000 True Fans — Kevin Kelly
   A short but enduring idea with a lot of relevance here. Kelly’s argument is simple: you do not need a massive audience to build a meaningful business. You need a small group of people who care deeply enough to keep showing up. It’s one of the clearest frameworks for understanding why niche expertise can outperform broader, shallower attention.

2. Show Your Work! — Austin Kleon
   This one pairs well with Montgomery’s argument that free content is not a threat to the business — it is often the front door. Kleon’s book is really about visibility, generosity, and the discipline of sharing what you know while you’re building. Useful for anyone who understands something valuable but hesitates to publish.

3. Company of One — Paul Jarvis
   A smart counterweight to the reflexive “scale at all costs” mindset. Jarvis makes a strong case for building leaner, more intentional businesses with clear economics and fewer moving parts. For a newsletter about expertise as an asset, this fits nicely.

4. The Business of Expertise — David C. Baker
   Probably the most directly on-theme recommendation this week. Baker writes about how experts package their thinking, price their value, specialize intelligently, and move from being one more service provider to being the obvious choice in a narrower category. Very relevant here.

5. Obviously Awesome — April Dunford
   This is a positioning book, which makes it especially useful for readers who know they’re good at something but have trouble explaining why it matters. Dunford is excellent on the gap between what a business does and how the market understands it. That gap is where a lot of expertise businesses stall.

6. The Almanack of Naval Ravikant — Eric Jorgenson
   Not a course-building book, but a sharp companion to the broader point of the essay. Naval’s thinking on specific knowledge, leverage, judgment, and ownership maps neatly to this idea that hard-earned expertise can become a real economic asset if you structure it properly.

More to explore

• ProCourseStart on LinkedIn

• Justin’s company: https://procoursestart.com

  
  Would you like a personal introduction to 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.

There’s a point in most businesses where things start to feel heavier than they should. It’s not obvious at first. On paper, everything looks fine—revenue is up, the team is growing, there’s more opportunity than there was six months ago. From the outside, it reads like progress. But inside the business, it’s a different story. Work slows down. Communication gets messy. You find yourself pulled back into things you thought you’d already handed off, fixing problems that shouldn’t be problems anymore.

Most founders interpret this as a growth issue. They assume they need more pipeline, more leads, more momentum. So they double down on the front end of the business—sales, marketing, visibility—anything that feels like forward motion. But that’s rarely where the problem lives.

In my experience, most businesses are actually pretty good at two things. They’re good at deciding what they want to do, and they’re good at doing the work—especially early on, when the founder is still close to everything. Strategy and execution tend to come naturally. What doesn’t come naturally—and what almost nobody builds intentionally—is the layer in between.

The part that teaches other people how to execute. The part that creates consistency. The part that makes it possible for the business to perform the same way on Tuesday afternoon without you as it does when you’re sitting in the room guiding it.

That middle layer is where most companies break.

When it’s missing, the business doesn’t actually scale—it stretches. You add more clients, more projects, more people, but the underlying structure doesn’t change. So the complexity compounds, and eventually everything starts to depend on the same person it always has —  the founder — and that’s where things get stuck.

Because at that point, it doesn’t feel like a systems problem. It feels like a people problem, a hiring problem, or a time problem. It feels like you just need to push a little harder, stay a little longer, stay closer to the work. So that’s what most people do. They become the quality control, the decision-maker, and the backstop.

Until they realize the business only works when they’re there to hold it together.

Eggs the Podcast veteran and founder of Agency Acquisitions, Nick Avaria, has spent a lot of time in that exact phase of business—the messy middle where companies have traction but can’t quite translate it into something repeatable. What’s interesting about his perspective isn’t that he’s seen it happen. It’s how consistently the root issue shows up in the same place: not in strategy, not in effort, but in the absence of the systems that connect the two.

The System Builder Behind the Scenes

Nick Avaria didn’t start in agencies. His early career was rooted in mergers and acquisitions, working on deals across industries before eventually moving into consulting and, later, building and scaling his own marketing agencies.

After helping grow and sell businesses—including scaling an agency past eight figures—Avaria shifted his focus toward advising other founders. Today, he works closely with agency owners and entrepreneurs who find themselves stuck in that familiar middle ground: too big to manage everything themselves, but not structured enough to scale cleanly.

His work centers on something most founders overlook—the systems, management layers, and feedback loops that sit between vision and execution. The part of the business that doesn’t get talked about much, but determines whether a company grows… or plateaus.

The Missing Middle, Defined

Avaria’s perspective is simple, but not easy: most businesses don’t fail because they lack effort—they fail because they never build the layer that makes effort scalable.

“You need to create the business in a way where you’re not needed.”

Actionable insight: If your involvement is required for delivery, sales, or decision-making, you don’t have a scalable business—you have a high-functioning job. Start identifying where you’re still the system.

“You have to wake up every single day figuring out how to replace yourself from every single thing that you do.”

Actionable insight: Replacement isn’t a one-time event. It’s a daily discipline. The founders who scale fastest are the ones actively working themselves out of roles—not deeper into them.

“The missing middle is this education thing… what are the elements that I need in order to drive behavior change?”

Actionable insight: Most teams don’t underperform because they’re incapable—they underperform because no one taught them how to succeed inside your business. Training and behavior systems are the multiplier.

“Everything must be measured and put into a dashboard… so it comes back up to strategy.”

Actionable insight: If performance isn’t visible, it isn’t manageable. Define 3–5 metrics per role and track them weekly. Not quarterly. Not “when things feel off.” Weekly.

“Scale is about the ability to deliver when you’re not in the room.”

Actionable insight: Test your business with a simple question: if you stepped away for two weeks, what breaks? Whatever breaks—that’s where your systems are missing.

“People underestimate the volume of systems you need to maintain quality control.”

Actionable insight: Systems don’t scale linearly—they compound. What worked at 3 people will collapse at 10. What worked at 10 won’t survive at 25. Build ahead of growth, not behind it.

“Most people think the problem is more sales… but the systems don’t enable them to scale.”

Actionable insight: Before chasing new revenue, audit your backend. Poor retention, inconsistent delivery, and broken ops will erase the upside of any new deals you close.

“The finish line isn’t that you know how to do it—it’s that someone else can do it without you.”

Actionable insight: Knowledge doesn’t scale. Transfer does. Record it, document it, train it—until execution no longer depends on you being present.

Where Most Businesses Get Stuck

There’s a version of this that plays out quietly in a lot of companies. The business grows just enough to become complicated, but not enough to become structured. And in that space, the founder becomes the system. They’re the one who knows how things should be done, who catches the mistakes, who steps in when something starts to slip. It works—for a while.

But it doesn’t scale.

At some point, the very thing that helped the business get off the ground becomes the constraint that keeps it from moving forward. Not because the founder isn’t capable, but because the business was never designed to operate without them.

The uncomfortable part is that fixing it doesn’t come from doing more. It comes from building the pieces that make “more” sustainable—clear expectations, measurable outcomes, repeatable ways of working, and people equipped to operate within them.

None of that is particularly glamorous. It doesn’t feel like progress in the way a new deal or a new hire does. But it’s the work that determines whether a business can actually grow into what it’s trying to become.

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. The E-Myth Revisited — Michael E. Gerber
   A foundational look at why most small businesses fail—and how systems, not people, create scalability.

2. High Output Management — Andrew Grove
   A practical guide to building effective management systems, feedback loops, and operational discipline.

3. Work the System — Sam Carpenter
   A tactical breakdown of how documenting and refining processes can transform chaotic businesses into scalable ones.

More to explore

• Nick Avaria on LinkedIn

• Nick’s company: AgencyAcquisitions.io

  
  Would you like a personal introduction to 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.

This week I attended the Bio Utah’s flagship Entrepreneur & Investor Life Sciences Summit here in Salt Lake City, Utah. The event gathers a familiar mix of people working at the intersection of science and business: research scientists presenting new technologies, early-stage founders hoping to turn those technologies into companies, and investors trying to determine which ideas might eventually become viable healthcare businesses.

The scientific innovation on display is remarkable. Across diagnostics, surgical technologies, imaging platforms, and digital health tools, there is no shortage of breakthroughs moving through research pipelines and startup labs. In fact, the scale of innovation in the life sciences sector is one of the reasons regions like Utah have become increasingly important hubs for healthcare entrepreneurship. According to BioUtah, the state’s life sciences ecosystem now includes more than 1,600 companies and supports roughly 180,000 jobs, contributing over $22 billion annually to the economy.

Kelvyn Cullimore, president and CEO of BioUtah, has pointed to the collaboration between universities, startups, and investors as a key driver of that growth, describing the emerging companies in the region as evidence of the “depth of innovation” developing across the research ecosystem.

In other words, innovation is not a scarce resource.

What becomes more interesting after spending time in rooms like this summit is the pattern that emerges in the conversations between founders and investors. During one portion of the event, several early-stage companies presented their technologies in a series of Shark Tank–style pitches. Each founder walked through the science behind their product, the size of the market opportunity, and the early traction they had achieved. The technologies themselves ranged widely—from fertility diagnostics and imaging agents to surgical devices and cardiac monitoring tools.

But once the presentations ended and the investors began asking questions, the conversation's focus shifted noticeably.

The questions were rarely about the underlying science. Instead, investors asked about commercialization strategy, regulatory pathways, reimbursement models, and adoption inside healthcare systems.

One investor asked a fertility diagnostics startup whether there was “broad awareness” of the product outside the small number of clinics already using it. Another investor pressed a surgical device founder on distribution strategy: would the company sell directly to hospitals, or rely on distributors to reach operating rooms? A cardiac screening company was asked how it planned to commercialize the product once regulatory approval was achieved, and whether it intended to build its own sales infrastructure or partner with existing healthcare providers.

The pattern repeated across the presentations. Investors wanted to understand regulatory timelines, reimbursement economics, and how the product would actually integrate into the clinical workflow of physicians and hospitals. In one exchange, a founder describing a new medical device was asked how hospitals would justify the cost of adopting it. The investor’s question was straightforward: could the company demonstrate measurable cost savings or improved outcomes that would motivate adoption?

What stood out about these conversations was not the skepticism of the investors. It was the consistency of their focus. Across very different technologies and markets, investors were asking essentially the same set of questions. They were trying to determine whether the company understood the system it would have to navigate.

Healthcare innovation has always been different from most other forms of entrepreneurship. A consumer technology startup can launch a product and quickly test whether users adopt it. Healthcare companies operate inside a far more complex environment. Regulatory agencies determine whether a product can be used. Payers determine whether it will be reimbursed. Hospital procurement systems determine whether physicians can access it. Clinical evidence determines whether doctors trust it.

The result is that innovation in healthcare must satisfy several different systems simultaneously before it reaches patients.

Large healthcare companies recognize this dynamic as well. Medtronic CEO Geoff Martha has argued that developing breakthrough medical technologies is only part of the challenge facing the industry. Ensuring those innovations can be delivered effectively and broadly within healthcare systems is equally critical to improving patient outcomes.

That reality also helps explain the growing focus on value-based care across the healthcare sector. Increasingly, reimbursement models are shifting away from simply paying for procedures and toward paying for measurable patient outcomes. The implication is that new technologies must demonstrate not only clinical effectiveness, but economic value within the broader healthcare system.

Seen through that lens, the questions investors asked during the pitch sessions begin to make more sense. They were not dismissing the scientific breakthroughs presented by the founders. They were trying to understand whether those breakthroughs could survive the structural realities of healthcare delivery.

In many ways, this points to a broader sequencing challenge that healthcare startups often face. The narrative of entrepreneurship tends to begin with the invention—the moment when a breakthrough technology or insight emerges. But in healthcare, the success of that breakthrough often depends on decisions that sit outside the laboratory. Questions about reimbursement strategy, clinical evidence generation, regulatory pathways, and provider adoption can determine whether innovation becomes widely used or quietly disappears.

None of this diminishes the importance of scientific discovery. Breakthrough technologies remain the foundation of progress in medicine. But the conversations at the summit offered a useful reminder that the path from innovation to patient impact rarely follows a straight line.

Healthcare is ultimately a system industry. Breakthrough ideas may begin the journey, but the system's structure determines whether those ideas reach the patients they are intended to help.

I know this was a little different from our typical Path newsletter, but I hope you found it interesting just the same.

As always, 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

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 Innovator’s Prescription — Clayton Christensen

   Christensen’s classic applies the theory of disruptive innovation to healthcare. The book argues that many of the inefficiencies in healthcare come from the way the system is structured—and that real breakthroughs often come from innovations that simplify care and move it to lower-cost settings. For anyone trying to understand why healthcare startups face such complicated adoption challenges, this book is still one of the clearest explanations.

2. The Patient Will See You Now — Eric Topol

   Topol explores how digital technologies, AI, and consumer access to medical data are reshaping healthcare delivery. While some of the predictions are ambitious, the book offers a thoughtful look at how the traditional healthcare system may evolve—and why innovation in medicine often collides with institutional inertia.

3. Loonshots — Safi Bahcall

   Not a healthcare book specifically, but extremely relevant for science-driven startups. Bahcall examines how breakthrough ideas often struggle to survive inside organizations and systems that are built for stability rather than experimentation. His concept of “loonshots”—wild ideas that eventually transform industries—offers a useful framework for understanding the tension between scientific discovery and commercial reality.

4. Redesigning Healthcare — Michael Porter & Elizabeth Teisberg

   One of the foundational books behind the modern push toward value-based healthcare. Porter and Teisberg argue that healthcare systems should compete on patient outcomes rather than the volume of services delivered. That shift toward outcome-based care is shaping how investors, providers, and payers evaluate new healthcare technologies today.

More to explore

• BioUtah — Utah’s Life Sciences Industry Organization

  https://bioutah.org

• CMS Innovation Center — Federal initiatives around value-based healthcare
  https://innovation.cms.gov

  
  Would you like a personal introduction to 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.

Most people don’t think about intellectual property until something goes wrong. A client relationship goes sideways. A contractor disappears. A competitor launches a brand that looks suspiciously similar to yours. Or you suddenly realize you’ve spent years creating value—but you can’t clearly explain what you actually own. In my experience in “agency-world,” that happens more than people like to admit because we tend to treat our work like output instead of assets. We ship the logo, the campaign, the deck, the website, and then move on to the next job. But the longer I’ve been in business, the more I’ve realized something simple: if you’re running a knowledge business, you’re not just delivering services—you’re running an intellectual property factory.

One of the biggest misconceptions—especially for creative people—is the idea that “I made it, so I own it.” Its equally common cousin is “I paid for it, so I own it.” In practice, both of those assumptions can get messy fast. If freelancers, contractors, partners, stock assets, templates, or outside tools were involved in the creation of something, you’ve introduced other parties into the ownership chain. The issue isn’t just legal theory—it’s leverage. Ownership is what allows you to reuse, repackage, license, defend, or sell the things you’ve built. If the ownership story is fuzzy, the business story gets fuzzy too.

What’s interesting is that most founders don’t start businesses thinking about intellectual property at all. They start because they’re good at something. A designer starts designing. A consultant starts consulting. A developer starts building software. For years, that’s exactly how I approached things in my own agency work. I was focused on the craft and the client outcomes, not necessarily on how the knowledge, systems, and ideas behind that work might become assets of their own. But over time, you start to realize that the real long-term value often lives in the patterns you’ve developed, the frameworks you’ve built, and the ideas you’ve refined—not just the one-off deliverables.

Part of what I love about writing this newsletter is that it lets me leverage intellectual property from another project I run—EGGS The Podcast. Every week we have long conversations with CEOs, founders, marketers, and innovators. Those conversations are valuable in their own right, but they also contain insights, frameworks, and ideas that deserve more than a single listen. By translating those conversations into newsletters like this one and placing additional focus on the key moments, I’m able to highlight ideas that might resonate differently with readers than they do with listeners. And that same core content can live in multiple forms—podcast episodes, newsletter essays, speaking topics, or even the podcasting course I’m currently building. Same intellectual property, different expressions of value.

That’s where things get especially interesting in the current moment, because tools like AI have made it easier than ever to generate content quickly. But speed and ownership are not the same thing. If a piece of work is entirely AI-generated, the ownership story becomes far less clear. And even when AI is used as a helper, questions about provenance, platform terms, and originality still matter. The temptation right now is to create more, faster, and cheaper. The smarter move is deciding which work is disposable and which work is a long-term asset—and being intentional about how those assets are created and protected.

All of this is why I was excited to sit down recently with Sharon Toerek on EGGS The Podcast. Sharon is a trademark and intellectual property attorney who works closely with agencies and other knowledge-based businesses—companies that are often creating valuable IP every single day without realizing it. Our conversation covered everything from common misconceptions around ownership to how founders can think more strategically about protecting and monetizing the ideas, systems, and creative work they’re already producing. If you’ve never really stopped to think about intellectual property as part of your business strategy, Sharon has a way of making the topic both practical and surprisingly relevant.

Seeing Business Through an IP Lens

Sharon Toerek is a trademark and intellectual property attorney and the founder of Toerek Law, a firm that works closely with marketing agencies and other knowledge-based businesses across the United States. Much of Sharon’s work focuses on helping companies protect the ideas, creative work, and systems that power their businesses—everything from trademarks and copyrights to contracts that govern how that work gets used and monetized. Over the years, she has developed a reputation for translating complex legal concepts into practical strategies that founders and agency leaders can actually apply.

One of the ways Sharon does that is through a framework she calls the IP Triangle—a simple lens for identifying the intellectual property that exists inside almost any business. At one point of the triangle is Brand: the names, slogans, and identifiers that signal who you are in the marketplace. Another point is Content: the creative or knowledge-based work you produce, whether that’s marketing campaigns, code, training materials, video, or written ideas. The third point is Transactions: the agreements and contracts that determine how that work is used, who owns it, and how it ultimately generates revenue.

The power of the triangle is that it makes something abstract feel visible. Instead of thinking about intellectual property as something reserved for tech companies or patent filings, Sharon encourages founders to see how much IP they are already producing every day. Once you start looking at your business through that lens, the conversation shifts—from reacting to problems after they happen to intentionally building and protecting assets that can grow in value over time.

Supercharging your IP factory

A few moments from my conversation with Sharon that reframed how I think about intellectual property inside a modern knowledge business.

“Legal for entrepreneurial companies should be regarded as a profit-making tool, a profit preservation tool… it’s intertwined with your ability to make and keep the money that your business is set up to earn for you.”

Actionable insight:
Most founders treat legal as an expense that shows up when something breaks. A better approach is to view legal structure as part of your revenue strategy—especially when your products are ideas, systems, and creative work.

“Most entrepreneurial companies undervalue the amount of IP they are creating on a day-to-day basis… it’s often their most significant asset.”

Actionable insight:
If you run a marketing agency, consultancy, course business, or software company, you are creating intellectual property constantly. The real question isn’t whether you have IP—it’s whether you’re documenting and protecting it.

“The misunderstanding is that if I paid somebody to create work for my company… I own that. Which is not the way the United States regards copyright law.”

Actionable insight:
Contractors, freelancers, and collaborators introduce ownership complexity. Without written agreements assigning rights to your company, the work may legally belong to the person who created it.

“You should be sitting down and doing an audit of your IP on a regular basis… look at the three points of the triangle.”

Actionable insight:
Sharon’s IP Triangle offers a simple audit:
• Brand — your name, marks, and identifiers
• Content — the work you produce
• Transactions — the contracts governing its use
If any corner is weak, your ownership story becomes harder to defend..

“The more you do along the way to build the legal fortress around your intellectual property… the more it’s going to be worth when you go to sell your company.”

Actionable insight:
Intellectual property doesn’t just protect what you’ve built—it increases enterprise value. Buyers, investors, and partners all look for clear ownership of assets before committing capital.

“The potential for creating a revenue stream that stands alongside your fee-for-service revenue… comes from intellectual property.”

Actionable insight:
Agencies often overlook the systems they’ve already built. Frameworks, training, tools, and methodologies can become courses, licensing models, or subscription products that generate revenue independent of billable work.

“The more shortcuts you take, the less value your innovation has.”

Actionable insight:
Tools like AI can speed up creation, but speed alone doesn’t build durable assets. Decide which work is disposable and which work is meant to become long-term intellectual property—and treat them differently.

Treat Your Ideas Like Assets

The thread running through Sharon’s perspective is pretty straightforward: most knowledge businesses are producing valuable intellectual property whether they realize it or not. The question is whether you treat those ideas as disposable output or as assets that deserve a little structure and protection.

Once you start looking at your business through that lens, the shift is subtle but important. Instead of simply delivering work and moving on, you begin to notice the frameworks, systems, and insights that could live beyond a single project or client engagement. Some of them might become products. Others might turn into teaching, licensing, or partnerships. At the very least, they become building blocks you can keep.

And in a world where tools can generate more content faster than ever, that distinction matters. Anyone can produce more “stuff.” The real opportunity is deciding which ideas are worth owning.

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 Sharon Toerek’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. Intellectual Property: The Tough New Realities That Could Make or Break Your Business — Paul Goldstein
   A business-minded look at trademarks, copyrights, trade secrets, and how to think about IP when your competitive advantage is ideas.

2. Built to Sell — John Warrillow
   Not an IP book, but it’s extremely relevant: it’s about building a company that can stand apart from the founder—often by packaging know-how, process, and repeatable “method” into something transferable.

3. Patent It Yourself — David Pressman (Nolo)
   More patent-specific than this newsletter needs, but it’s a solid example of what “practical, step-by-step IP guidance” looks like—useful if your audience includes inventors, product builders, or anyone sitting on potentially patentable work.

More to explore

• Legal+Creative - Sharon Toerek’s Official Site: https://legalandcreative.com

  Contact Mike: https://www.linkedin.com/in/sharontoerek/
  
  Would you like a personal introduction to 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

Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://ryanroghaar.com

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

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 last year or so, I’ve noticed a quiet shift in the way business owners talk about marketing. The question used to be, “What should we say?” Now it’s more often, “What tool should we use?” AI has moved so quickly into the conversation that it feels less like an option and more like an obligation. If you’re not using it, you’re behind. If you are using it, you’re still wondering whether you’re using it enough.

And I understand the appeal. AI produces output. It gives you something tangible. A blog post, a campaign outline, a positioning draft, a list of taglines. For founders and operators who are already juggling too much, that kind of leverage feels like relief. It feels like momentum.

But the more I’ve watched this play out—both in my own work and in the companies we support—the more I’ve started to question whether we’re confusing production with progress. It’s easier than ever to generate content, but it’s not any easier to decide what you stand for, to define your value, or differentiate in a crowded market. In some ways, the abundance of tools makes it easier to avoid that work.

I’ve caught myself reaching for the tool before I’ve done the thinking. Instead of sitting with the harder questions — who are we really for, what are we willing to compete on, what are we not going to chase — it’s tempting to start building. Draft something. Ship something. Post something. Movement feels productive, even when direction is unclear.

The danger isn’t that AI produces bad work. In many cases, it produces very good work. Clean. Structured. Persuasive. The danger is that it can make undifferentiated ideas look polished. And polish can hide the fact that nothing underneath has actually been decided. You can sound clear without being clear.

And that’s what I’ve been wrestling with lately: not whether AI is useful — it is — but whether we’re letting tactics replace thinking. Whether we’re accelerating execution while neglecting strategy. That’s why my conversation with Eggs! The Podcast guest, Mike Snyder — retired Marine Corps Lieutenant Colonel, agency founder, and author of The Great Marketing Lie — was so compelling. Mike has spent decades watching marketing evolve from Yellow Pages ads to SEO to social media, and now AI, and his perspective is refreshingly simple: tools change, but strategy doesn’t. We talked about why AI is tactical, why positioning still belongs to leadership, and how businesses that skip the hard thinking end up producing more noise instead of more value.

The Tool Isn’t the Strategy

Mike Snyder is a retired Marine Corps Lieutenant Colonel who has spent the last several decades operating at the intersection of leadership, strategy, and marketing. After serving in public affairs roles around the world, he transitioned into business, building and leading multiple companies — including a marketing consultancy that has supported hundreds of organizations across industries.

Over the course of his career, Mike has watched marketing evolve from Yellow Pages ads to search engines, from social media to AI. He has taught MBA students, advised executive teams, and helped founders rethink how they position, price, and differentiate their businesses. His work centers on a simple but often neglected premise: marketing isn’t the website, the ads, or the content. It’s the strategic decision about why a business exists and what unique value it creates.

He is also the author of The Great Marketing Lie, and managing partner at RSM Marketing, where he challenges the idea that marketing is inherently complex and argues instead that most businesses make it harder than it needs to be — often by confusing tactics with strategy.

Strategy Before Tools

In our conversation, Mike kept returning to one core distinction: marketing communications changes constantly, but marketing strategy does not. AI may be the newest tool, but it doesn’t replace the thinking that determines whether your business actually stands out.

“How can we think strategically now that we’ve got 11 and a half months to go rather than act tactically? Because that’s the tail wagging the dog.”

Actionable insight:
It’s easy to let new tools dictate your agenda. When a platform shifts or AI improves, the reflex is to respond immediately. But strategy should determine which tactics matter — not the other way around. Before asking what tool to use, ask what position you’re trying to strengthen.

“AI is a tactic. Not a strategy.”

Actionable insight:
If that’s true, then it belongs in the execution layer — after the positioning has been decided. AI can help you write the email, build the landing page, and refine the messaging. It cannot determine what you’re competing on, how you’re priced, or what makes you different. Those are strategic decisions. If those aren’t clear first, AI just accelerates whatever ambiguity already exists.

“A lot of business owners think marketing is the website… I call that marketing jazz.”

Actionable insight:
Websites, ads, and content are visible. They feel like marketing because they’re tangible. But they are execution layers. Marketing, at its core, is answering a much harder question: Why does this business exist, and what unique value does it create that customers will pay for? The “jazz” only works when the composition underneath is sound.

“There’s no rule that says you have to describe your company the way everyone else does.”

Actionable insight:
Most businesses compete inside the category they’ve been handed. Same language. Same labels. Same comparison set. What Mike pointed out is that you can change the category simply by changing how you define yourself. His firm didn’t change its services. It changed how it framed them — and suddenly it wasn’t competing with the same agencies anymore. If you’re stuck in a crowded market, the first move isn’t necessarily to add something new. It might be to redefine what you already do.

“When we develop strategy, I use a simple test: how do we make this easier for the customer?”

Actionable insight:
When developing strategy, Mike asks a simple question: How do we make this easier for the customer? Easier to understand. Easier to buy. Easier to justify internally. Companies often chase complexity when clarity wins. If you can make the value obvious and reduce friction, you’ve already created an advantage.

“The enemy of easy is busy.”

Actionable insight:
Most teams don’t struggle because they lack tools. They struggle because they never slow down long enough to simplify. When everyone is moving, producing, responding, and reacting, complexity creeps in. Strategy gets replaced by activity. If you don’t create space to think, you default to doing — and doing is rarely the same thing as differentiating.

“They’re not thinking retention. They’re thinking acquisition.”

Actionable insight:
Most growth conversations start with leads. More traffic. More reach. More visibility. But if customers don’t stay, none of that matters. Retention forces you to confront whether the value is real, whether the product actually fits, and whether switching would hurt. Acquisition is exciting. Retention is revealing. If you build for the latter, the former usually follows.

The New Marketing Lie

AI isn’t going anywhere. It will keep improving. It will keep getting embedded into every workflow, every platform, every operating system. The companies that ignore it will fall behind. But the companies that treat it like strategy will make a different mistake.

What we kept circling back to in this conversation was simple: marketing communications evolves; marketing fundamentals do not. Positioning still matters. Differentiation still matters. Retention still matters. Making it easier for the customer still matters. You can automate execution. You can automate execution. You cannot automate clarity — and confusing the two is the real mistake

Every new wave of technology creates the same temptation — to reach for the tool before doing the thinking. AI just makes that temptation faster and more convincing. But strategy still belongs to leadership. It belongs to the founder. It belongs to the person willing to slow down long enough to decide what the business is and isn’t.

Use the tools. Accelerate the work. Just don’t confuse the accelerator for the direction.

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 Mike Snyder’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 Great Marketing Lie – Mike Snyder
   A practical, experience-driven breakdown of why marketing isn’t inherently complex — and why most businesses make it harder than it needs to be by confusing tactics with strategy.

2. Start With Why – Simon Sinek
   A reminder that clarity of purpose precedes communication. If you don’t know why you exist, no amount of messaging will fix it.

3. Purple Cow – Seth Godin
   A classic on differentiation. In crowded markets, being “good” isn’t enough — you must be remarkable.

4. The 7 Habits of Highly Effective People – Stephen Covey
   Not a marketing book, but foundational thinking around discipline, intentionality, and long-term effectiveness.

5. Good Strategy / Bad Strategy – Richard Rumelt
   A sharp explanation of what real strategy looks like — and how often leaders mistake goals and buzzwords for actual strategic direction.

More to explore

• RSM Marketing: https://rsmconnect.com

• Contact Mike: https://www.linkedin.com/in/mikesnyderraptorusa
  
  Would you like a personal introduction to 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.

Work with me

Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://ryanroghaar.com

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

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.

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

I’ve spent most of my career in relationship-driven work. I understand the value of people. I understand how trust is built, how partnerships form, and how much of business success comes down to how well you treat others when there’s nothing contractual forcing you to do so. None of that is new to me.

What I didn’t fully appreciate until recently is just how much a company’s culture can determine whether those values actually survive at scale.

It’s one thing to believe in human connection. It’s another thing entirely to build an organization where that belief consistently shows up in how people communicate, how they handle stress, and how they treat customers when no one’s coaching them in real time. That gap, it seems, is where a lot of customer experience problems begin to emerge.

Like most, I think the assumption was that customer service issues were primarily frontline problems. If something broke down, the fix seemed obvious: better scripts, better tools—better people—another channel layered on top. Those things help, but only temporarily. What I’ve come to understand is that customer service is rarely the root issue. It’s a lagging indicator of internal health.

When service feels inconsistent or impersonal, it’s often not because someone forgot how to be polite. It may be because something upstream isn’t working. Culture, trust, clarity, accountability—those forces don’t stay neatly inside the organization. They leak. And when they do, customers feel it immediately.

This is why so many attempts to “fix” customer experience fall flat. You can’t automate your way out of internal dysfunction. You can’t script around disengagement. And you can’t use technology to compensate for teams that don’t feel aligned or supported.

Internal friction always shows up externally.

You see it in how teams talk to each other under pressure. Gossip, quiet resentment, unclear ownership, people talking sideways instead of directly—none of that feels dramatic in isolation. But over time, it erodes patience and trust. Tone changes, attention slips, and eventually, those shifts reach the customer.

Customers don’t hear internal conversations, but they experience their results.

This is also where a lot of enthusiasm around AI and automation misses the point. These tools can improve efficiency and coverage, but they don’t create great service on their own. In fact, when internal systems are weak, automation often just scales the problem faster. Technology doesn’t fix culture. It amplifies it.

Good customer service isn’t something you design once and install. It’s something your organization produces over time—through who you hire, what behavior you tolerate, and whether your systems evolve as the company grows. What works at five people breaks at fifty. What feels obvious early becomes invisible later unless leaders are paying attention.

That’s why my conversation with Eggs! The Podcast guest, Nathan Strum, co-founder of Abby Connect, was so compelling. Nathan has spent more than two decades building a company where customer service isn’t treated as a department or a talking point, but as the natural output of culture, enforcement, and operational discipline. We talked about what it takes to sustain real service quality at scale—and why so many companies underestimate the role internal culture plays in the experience customers ultimately receive.

When Customer Service Is the Business

Nathan Strum is the co-founder and CEO of Abby Connect, a company he started more than twenty years ago after an unlikely beginning in a family-run executive office business. What began as answering phones for tenants inside a single building eventually became a full-scale reception service supporting thousands of small and mid-sized businesses across the country.

From the start, Abby Connect was built around a simple idea: if you can’t outspend or outscale bigger competitors, you win on service. That philosophy traces back even earlier for Nathan, who grew up in family businesses where customer relationships—not branding or technology—were the primary differentiator. As Abby scaled from a tight-knit family operation into a multi-hundred-person organization, that same service-first mindset forced Nathan to confront a harder challenge: how to preserve trust, tone, and accountability as headcount grows and systems strain.

Today, Abby Connect operates at the intersection of people, process, and technology. Nathan has spent years navigating the uncomfortable realities of scaling culture—enforcing standards, addressing internal friction, and reworking systems that no longer serve the customer. More recently, that work has extended into thoughtfully integrating AI as a support layer for service delivery, not a replacement for human judgment. The result is a company that treats customer service not as a department, but as the output of internal health.

Culture Is the System That Produces Service

In our conversation, Nathan shared hard-earned lessons from building a service business over two decades—lessons that cut through buzzwords and focus on what actually sustains customer experience at scale. The quotes below highlight how internal discipline, cultural enforcement, and realistic use of technology shape what customers ultimately feel.

“The way we beat bigger competitors was customer service. That lesson never changed.”

Actionable insight:
When you don’t have the advantage of scale, brand, or capital, service becomes strategy—not a support function. This mindset doesn’t disappear as companies grow; it becomes harder to protect, and more important to enforce..

“As you grow, the hardest part isn’t adding people — it’s maintaining the standards that used to happen naturally.”

Actionable insight:
Culture isn’t defined by perks or values statements. It’s defined by enforcement—especially when addressing behaviors that quietly undermine trust, alignment, and morale.

“Gossip is like a cancer. It tears organizations apart if you let it spread.”

Actionable insight:
Internal communication patterns directly affect external experience. When teams normalize gossip or indirect communication, confusion and frustration eventually surface in customer interactions.

“Every time we hit a ceiling, we had to throw out the rulebook and rebuild the company.”

Actionable insight:
What works at one stage of growth often becomes the very thing that breaks service quality at the next. Scaling customer experience requires leaders to let go of systems they’re proud of before those systems fail customers.

“You can’t automate your way out of edge cases.”

Actionable insight:
Great service lives in the margins—accents, emotions, misunderstandings, and moments of friction. Technology can support coverage, but human judgment is what preserves trust when things don’t go as planned.

“We hire for personality and train for skill.”

Actionable insight:
Customer service quality is shaped long before the first customer interaction. Hiring for openness, critical thinking, and coachability creates teams that adapt under pressure instead of defaulting to scripts.

“Technology doesn’t fix culture. It amplifies it.”

Actionable insight:
AI and automation don’t improve service on their own. They magnify whatever already exists inside the organization—good or bad—making internal health more important, not less.

Customer Service Is the Outcome, Not the Fix

What stayed with me after this conversation wasn’t a new framework or a clever tactic. It was the reminder that customer service is rarely improved by focusing on the customer alone. The companies that deliver consistently good experiences tend to do so almost indirectly—by paying attention to the internal conditions that make good service possible in the first place.

Culture, in that sense, isn’t abstract. It’s practical. It shows up in how teams talk to each other, how standards are enforced as companies grow, and how leaders respond when the easy fixes stop working. When those internal systems are healthy, customer service feels natural. When they’re not, no amount of tooling, scripting, or automation can fully compensate.

Technology will continue to change how businesses interact with customers, and AI will undoubtedly play a larger role in that future. But the core lesson remains the same: tools don’t create trust—people and systems do. The organizations that understand this will use technology to extend their culture, not replace it. And the ones that don’t will keep chasing customer experience problems that were never customer-facing to begin with.

If customer service feels harder than it should, the answer probably isn’t another feature or platform. It’s a closer look at what’s happening upstream—and whether the culture behind the service is actually being protected.

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 Nathan Strum’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. Never Eat Alone — Keith Ferrazzi
   A foundational book on relationship-driven work. Ferrazzi’s core idea—that long-term success is built through trust, generosity, and consistent human connection—maps directly to the idea that customer service is an outcome of how people are treated internally.

2. The Culture Code — Daniel Coyle
   One of the clearest explanations of how high-performing cultures are actually built. Not through perks or slogans, but through shared behaviors, signals, and enforcement. A great companion to the idea that customer service is downstream of internal health.

3. The Hard Thing About Hard Things — Ben Horowitz
   A brutally honest look at leadership when the easy answers stop working. Horowitz does a good job of articulating why culture decisions—especially uncomfortable ones—matter most when companies start to scale.

4. Setting the Table — Danny Meyer
   A classic for anyone thinking about service as a strategic advantage. Meyer’s philosophy reinforces the idea that great customer experience starts with how teams are treated and empowered behind the scenes.

More to explore

• Abby Connect: Abby.com

• Contact Nathan: https://www.linkedin.com/in/nathanstrum/
  
  Would you like a personal introduction to 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.

Work with me

Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio

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

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.

Most people talk about “luck” like it’s a weather pattern. You get a good break. You catch a trend early. You happen to meet the right person at the right time. And sure—timing matters. But what I’ve noticed after years of working around founders, operators, and investors is that the people who seem lucky usually have something else going on: they’re running a repeatable process that keeps putting them in the path of good outcomes.

It’s not mysterious. It’s almost boring. They learn the product at a use-case level—not “our platform is powerful,” but what problem does this solve on a Tuesday afternoon in a real business with real constraints? They talk to the people closest to the work. They talk to customers until the story stops being flattering and starts being useful. Then they look sideways at competitors—not to copy them, but to understand the shape of the market and where the easy assumptions are hiding.

In other words: they triangulate. They don’t fall in love with a single viewpoint, even their own. They collect inputs until the pattern is obvious, then they pick a direction and live with the consequences. That last part matters. A lot of folks can diagnose. Fewer can decide. Even fewer can execute without constantly reopening the question to soothe their nerves.

This is where “making your own luck” starts to look less like motivation and more like a craft. It’s also where ego becomes expensive. If you’re the kind of leader who needs everyone to agree with you, you’re going to be surrounded by polite people and slow data. If you’re the kind who can hear “this isn’t working” without taking it personally, you can move faster than your competitors—because you’re not dragging feelings behind every decision like a boat anchor.

And yes—AI is changing the game here, but not in the way the headlines want. The real advantage isn’t that AI is “smart.” It’s that it lowers the cost of iteration. It compresses research time. It speeds prototyping. It turns previously painful work—like scanning contracts, writing first-draft code, or testing a hypothesis—into something you can do before lunch. That doesn’t replace judgment. It just raises the bar for people who refuse to develop any.

The operators I trust tend to share the same posture: curious, blunt, and allergic to fantasy. They’ll change the business model, fire the wrong customers, kill the wrong product line, and rebuild the engine while the plane is in the air—because the alternative is slowly losing. That isn’t chaos. That’s discipline.

Few people articulate this “luck is built” mindset better than this week’s guest, Eggs! The Podcast alum and CEO of Agilence, Russ Hawkins—an intrapreneur-turned-turnaround CEO who has spent decades walking into complicated businesses, telling the truth about what he finds, and then building a plan that actually ships.

From Bell System Chaos to Retail Analytics Clarity

Russ Hawkins is the CEO of Agilence (Agilenceinc.com), a data analytics company that helps multi-location businesses make sense of the operational data piling up inside retailers, restaurants, convenience stores, pharmacies, and hotels. In plain terms: Agilence pulls together feeds from across a business and helps leaders ask—and answer—questions that improve performance.

Russ’s career path makes his perspective unusually grounded. He spent roughly 15 years inside AT&T during the era of the Bell System breakup and the reinvention of telecom, building a reputation as someone who could innovate inside a large machine without becoming a prisoner of it. Later, he moved into venture-backed leadership, repeatedly stepping into companies that needed what he calls “adult supervision”—a clearer strategy, a tighter go-to-market, and the willingness to stop doing things the hard way just because that’s how they started.

He’s now been at Agilence for 18 years, including a major reinvention of the business in 2013—shifting away from hardware headaches and into a more scalable software-driven model. His operating style is consistent: talk to everyone, corroborate the story with customers, understand the competitive landscape, then make the call and execute.

How to Build “Luck” on Purpose

Russ doesn’t romanticize leadership. He treats it like field work: collect inputs, tell the truth, decide, and move.

“First thing I do when I come in is talk to everybody.”

Actionable insight:
When you take over a team or a business line, skip the “strategy offsite” theater. Do fast, structured listening tours—employees, customers, and anyone who touches the product daily. The truth shows up quickly if you’re willing to hear it.

“I also went… to all the existing customers… and tried to corroborate and triangulate.”

Actionable insight:
Internal confidence is cheap. Customer corroboration is expensive and therefore valuable. If your internal narrative doesn’t match what customers say they’re buying, you don’t have positioning—you have a bedtime story.

“I would identify the top three competitors… and meet the CEOs… ‘How do we work together even knowing that we’re competitive?’”

Actionable insight:
Competitors are a source of market clarity, not just a threat. You learn how they frame the category, where they’re vulnerable, and what customers already expect. That’s the difference between building in a vacuum and building with context.

“I never promised them that I would be able to make anything happen… All I promised them was that I would do an analysis.”

Actionable insight:
This is the grown-up version of leadership credibility. Don’t sell certainty. Sell process. Investors, boards, and teams can forgive bad outcomes faster than they can forgive fuzzy thinking.

“There’s only three things that I do… strategic direction… allocating capital… hiring the right people.”

Actionable insight:
This is a useful filter when you feel buried. If what you’re doing isn’t one of those three (or doesn’t directly support them), it’s probably a delegation problem or a distraction dressed up as responsibility.

“Bootstrap as long as you can… [Investors] are friendly, but they’re not your friends.”

Actionable insight:
If you raise too early, you trade optionality for oxygen. Sometimes you need the oxygen. But don’t pretend the incentives match—because they don’t. The best leverage you’ll ever have is the leverage you built before you needed it.

“We make our own luck.”

Actionable insight:
Luck isn’t the spark. Luck is what people call your results when they didn’t see the inputs: the calls, the uncomfortable conversations, the competitor research, the customer interviews, the early exits, the fast rebuilds.

The Luck You Can Actually Control

There’s a quiet relief in Russ’s framework: you don’t need to be a genius, and you don’t need to predict the future. You need a system that keeps you close to reality, close to customers, and honest about what’s working. That’s where good decisions come from—and good decisions compound the way luck is supposed to.

It also reframes what “boldness” really is. Boldness isn’t swagger. Boldness is being willing to kill the product line that’s draining you. Boldness is walking away from the wrong customers, even if they’re loud. Boldness is telling the truth early—before the business forces you to learn it in a more expensive way.

And if you’re building right now, this is a good week to steal a page from Russ: pick one assumption you’ve been protecting, then go try to disprove it. Call five customers. Call two ex-customers. Look at a competitor’s pitch. Ask your team what they think you’re ignoring. Then write a plan you can execute without needing everyone to clap first.

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 Russ Hawkins’ 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. High Output Management — Andrew Grove
   A practical operating manual for building systems that scale: decision-making, leverage, and how managers actually create output.

2. The Outsiders — William N. Thorndike
   A sharp look at CEOs who win through capital allocation and disciplined decision-making—less charisma, more compounding.

3. The Lean Startup — Eric Ries
   Not for the buzzwords—read it for the discipline: test assumptions, shorten cycles, learn fast, “lose early.”

4. Zero to One — Peter Thiel
   Useful as a counterpoint: where contrarian bets come from, and how to think about category creation (even if you disagree with half of it).

More to explore

• Agilence: Agilenceinc.com

• Contact Russ: R. Hawkins at Agilenceinc.com

Work with me

Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio

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

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

Would you like a personal introduction to 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.

Get featured

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