Most founders don’t set out to lose their soul.

They start with a real problem they want to solve, a group of people they want to serve, and a set of values they believe will guide them through the hard days. They pour everything into building something meaningful.

Yet time and again, something shifts. The company they created slowly becomes unrecognizable to their customers, their employees, and often to themselves.

When entrepreneur, author, and Lean Startup creator Eric Ries joined me on the Passion Struck podcast, to discuss his new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, he offered a sobering answer. The greatest threat to an organization’s character usually isn’t failure.

It’s success.

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Success Doesn’t Protect You—It Makes You More Vulnerable

We tend to believe that once we hit product-market fit, raise enough money, or reach a certain size, we’ll finally have the freedom to run things the right way. We assume our values will be safe.

This assumption is entirely wrong.

The reality is that the more successful an organization becomes, the more valuable it is as a target for extraction.

Eric has watched this play out with countless founders. The more successful the company becomes, the more it attracts pressure to extract value at the expense of everything that made it special. He calls this force financial gravity, an invisible pull that quietly reshapes decisions, priorities, and eventually culture.

Financial gravity shows up in small moments: when someone chooses not to speak up in a meeting because “investors might not like it.” When a team opts for the easier, slightly compromised path because it looks better on next quarter’s numbers. Over time, these small choices become the default. What starts as survival becomes habit, and habit becomes culture.

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The Story of Sol Price and Costco

One of the clearest examples comes from retail legend Sol Price.

In 1954, the brilliant attorney-turned-retailer Price founded FedMart on a simple but radical idea: the customer is my client, and I have a fiduciary duty to them. He built the modern discount retail model with extraordinary integrity, once posting competitors’ ads in his own stores with signs that said, “Don’t buy this from me. You can get it cheaper down the street.”

FedMart thrived. But going public brought relentless pressure to raise prices and cut costs. Price refused. So his investors changed the locks on his office and removed him. Without his guiding hand, the company pursued faster profits and went bankrupt within seven years.

But the story doesn’t end there.

A young executive named Jim Sinegal had quit FedMart in protest when Price was ousted. He later helped Price launch Price Club and eventually co-founded Costco. Today, Costco is a $400 billion public company that still operates with the same customer-first principles: capped margins, above-market wages, and a stubborn refusal to compromise on quality.

The difference? Costco was built with structural integrity and governance choices that protect the original mission from financial gravity. Good intentions weren’t enough. They created safeguards.

Costco’s success reveals something important. Values don’t survive because leaders talk about them. They survive because they’re embedded in the structures, incentives, and stories that shape everyday decisions.

Which raises an important question: What happens inside an organization when no leader is present?

When No One Is Watching

This is where leadership gets interesting.

Most important decisions in a company happen when no manager is in the room. Will the customer service rep go the extra mile? Will the product team resist making it just a little worse to hit margins? Will someone speak up when they see the company drifting?

Eric draws on the work of Mary Parker Follett, a pioneering thinker from the 1920s, who introduced the idea of the invisible leader, a shared sense of purpose so strong that it guides people even when no one is watching.

A powerful example comes from HEB, the beloved Texas grocery chain. During a severe ice storm, one of their stores lost all power, including backup systems. Point-of-sale terminals went down. Customers who had stocked up for the storm suddenly couldn’t pay.

Instead of waiting for headquarters or calculating the cost, the store manager told everyone to take their groceries and go home. No charge. This wasn’t an exception to HEB’s culture. It was an expression of it.

Good Intentions Are Not Enough

Eric’s message isn’t that leaders should abandon growth. It’s that growth without protection eventually puts purpose at risk.

Whether you’re leading a company, a team, or even a family, values survive when they’re reinforced by structures, habits, and accountability rather than good intentions alone.

As leaders, we can’t simply command culture or values into existence. These are emergent properties, like health in the human body. You can’t order your body to heal faster, but you can create the conditions that make healing more likely.

That’s why I talk about gardener leadership. In the military, especially in special operations, you can’t micromanage teams operating far away. You give them a clear purpose, strong training, and the right environment, and then trust them to execute. The same principle applies in business, teams, and even families.

Your job is to cultivate the conditions where the right things happen naturally.

Protecting What Matters

The companies that endure don’t rely on good intentions alone. They build structures that protect what matters when pressure arrives.

The same principle applies to our teams, our families, and our lives. Values erode when we assume they’ll survive without deliberate protection.

In the end, the ultimate measure of our work is not how much success we manage to accumulate. It is how deeply we protect our humanity, our trust, and the people who rely on us while we are still here to lead.

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A Question for You

Have you ever watched an organization you cared about, whether a company, a team, or even a community group, slowly drift away from what made it special?

What’s one structural or cultural choice you could make right now to better protect what matters most in your work or life?

Drop a comment below. If this resonated, share it with a founder, leader, or friend who’s trying to build something that lasts.

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Listen to Episode 775 with Eric Ries for the full conversation on resisting financial gravity, mastering structural governance, and building an incorruptible organization that stands the test of time.

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Thank you for being an active part of this ecosystem.

© John R. Miles 2026. All rights reserved.

When most people hear Blake Mycoskie’s story, they think of impact, innovation, and success. The young entrepreneur who turned a trip to Argentina into a movement that gave away over 100 million pairs of shoes. Financial freedom. Global recognition. A beautiful family.

From the outside, it looked like the ultimate arrival.

But as Blake revealed on my podcast Passion Struck, the reality was far more painful. After selling TOMS, he was left confronting a truth many high-achievers know too well: massive external success does not heal an internal wound.

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The Hidden Trap of a Performance-Driven Scoreboard Identity

Blake traces much of the pattern back to competitive tennis. At fifteen, he moved away from home to train at the John Newcomb Academy in Texas. His days revolved around rankings, repetition, pressure, and performance.

What struck me was that he didn’t describe this as something imposed on him by demanding parents. The pressure came from within. Over time, performance became the structure through which he learned to evaluate himself.

When an Achilles injury ended his realistic shot at becoming a professional player, the underlying dynamic didn’t disappear. It simply migrated into entrepreneurship. The tennis player became the young founder. Wins became company launches, growth, impact, and recognition.

“I had this core wound that I never really addressed… I just never felt that I was enough.”

That pattern is more common than many high performers realize. Achievement becomes emotionally regulating. Success briefly quiets insecurity, so the nervous system learns to keep chasing the next milestone, believing peace exists just beyond it.

The nervous system learns early: Perform → Receive praise → Feel temporary relief. The cycle repeats across arenas (sports, business, influence) without ever resolving the underlying deficit.

The scoreboard changes. The psychological contract remains the same.

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What Happens When Massive External Success Fails to Heal the Wound

After selling TOMS, Blake had the kind of life many people spend decades pursuing. He had wealth, freedom, influence, and the knowledge that his company had materially impacted millions of lives.

Yet once the momentum slowed, something unsettling surfaced.

“I helped 100 million kids get shoes. I made hundreds of millions of dollars. I had a great family. And that still wasn’t enough.”

This is one of the least discussed aspects of achievement culture. As long as a goal remains unfinished, we can project fulfillment into the future. But once the achievement arrives, the emotional structure underneath it becomes impossible to ignore.

For Blake, that realization triggered years of depression, emotional numbness, a misdiagnosis of bipolar disorder, heavy psychiatric medications, and eventually a terrifying period of active suicidal ideation. He described it with raw honesty — no attempt to turn it into a clean redemption arc. It was a long, painful confrontation with the limits of what external success could actually provide.

The Difference Between Ambition and Self-Worth

What eventually changed for Blake was not the disappearance of ambition. He still launches companies (including Morning Water), advises startups like the AI therapy app Sonia, hosts a podcast, and leads the Enough movement.

What changed was the emotional role achievement played in his life. He no longer needed accomplishments to function as evidence that he deserved worth.

Through therapy, inner child work, psychedelics, and especially a 40-day mantra-based meditation practice, Blake shifted from “I must achieve to prove I’m enough” to a full-body realization: “I am enough simply because I exist.”

That shift didn’t make him passive. It made him lighter. He now starts mornings making eggs for his kids (even if they don’t eat them) and moves through his days without tying his identity to business outcomes or public opinion. The pressure is gone. Curiosity and contribution remain.

Why the Enough Movement Resonates So Deeply

Out of this hard-won clarity came the Enough movement. At its center is a simple but powerful ritual: a set of beautiful beaded bracelets. You keep one as a daily reminder and give the other away. One hundred percent of profits support mental health organizations, especially those serving students.

The bracelets themselves are not magic. What matters is what they create: permission.

Permission to speak honestly. Permission to acknowledge struggle without performing strength. Permission to tell another person they matter beyond what they produce.

Blake shared moving stories — strangers connecting in coffee shops over matching bracelets, and a high school girl who finally opened a conversation with her depressed father by giving him the second bracelet.

In an age where 64% of people don’t feel they belong at work, 74% don’t feel they belong in their communities, and nearly 50% of Americans will face a mental health diagnosis in their lifetime, this matters profoundly. Mattering has become dangerously conditional.

How to Stop Chasing External Validation and Discover Intrinsic Worth

The shift wasn’t about abandoning ambition. Blake continues building and creating. What changed was the source of his drive.

He reprogrammed his subconscious through deep inner work and now operates from a grounded sense of identity rather than emotional repair. Today, he pursues excellence out of curiosity, contribution, and joy rather than compensation.

Practical shifts Blake emphasizes:

• Daily reminder practices — like wearing the Enough bracelet as a physical signal that you are enough.

• Judgment-free processing tools — such as the CBT-trained AI therapy app Sonia for those 5 a.m. anxiety moments when a human therapist isn’t available.

• Radical honesty with others — using visible signals (like the bracelet) to create permission for real conversations about mental health.

• Stripping away performance — simplifying life, protecting relationships with kids, and refusing to sacrifice balance on the altar of the next win.

The Relief of No Longer Negotiating Your Worth

The most powerful part of Blake’s story isn’t the success or even the darkness — it’s the relief on the other side.

Relief that you can still create, build, and strive without carrying the crushing weight of “not enough.” Relief that ambition and self-worth don’t have to be fused forever. Relief that you can show up as a parent, leader, or founder without your entire identity on the line every day.

If you’re a high performer who has ever achieved something big only to wonder why it still doesn’t feel like enough, Blake’s message is simple but profound:

You don’t have to earn your worth. You already have it.

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What about you?

Have you ever reached a major milestone only to feel the same emptiness afterward? What helped (or is helping) you separate your achievements from your inherent worth?

Drop a comment below. And if this resonated, share it with someone who needs the reminder — they might just be waiting for permission to stop performing and start healing.

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Ready to start your own Enough journey?
Visit WeAreEnough and grab a bracelet for yourself and someone who needs to hear they matter.

Blake Mycoskie was a guest on Passion Struck. Listen to the full conversation for more of his story, including details on mental health tools, parenting from a place of enough, and building the Enough movement.

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© John R. Miles 2026. All rights reserved.

There is a particular kind of shame that arrives not when you fail, but when you fail as yourself.

has spent his entire career studying emotional health. He knows the anatomy of a panic attack. He knows, almost instinctively, how to talk someone down from the ledge of their own fear. Compassion is not just his profession — it is, by every account, his nature.

So when a neighbor in an elevator began pounding on the doors, hitting every button, dissolving into panic, Guy knew exactly what to do.

And he snapped at him instead.

Not a gentle redirection. A sharp, uncharacteristic “this is my nightmare” — the kind of response that belongs to someone depleted, not to someone whose life’s work is the opposite of depletion. He was one year into his dream career. He had nothing left to give.

I’ve been thinking about that elevator moment ever since our conversation. Not because it’s a cautionary tale about burnout — we have plenty of those. But because of what it quietly reveals about the nature of the grind.

It doesn’t announce itself. It doesn’t arrive with a warning label or a dramatic breaking point. It seeps. It finds the edges of who you are and slowly, almost imperceptibly, begins to soften them. And you don’t notice until the moment you act like a stranger to yourself — until you snap in an elevator, or come home and have nothing left for the people you love most, or sit across from your own life and feel oddly absent from it.

That’s the thing nobody tells you about working too hard. It doesn’t just take your time. It takes you.

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The Stool With One Leg

In Passion Struck, I used an image to describe burnout — because I lived it long before I had words for what it was.

Imagine a stool. Not a chair — a stool, the kind that requires balance. It has several legs: your health, your relationships, your inner life, your sense of play and curiosity, and rest.

And then there is work.

When the grind takes hold, work doesn’t just grow — it crowds. The other legs don’t snap dramatically; they quietly dissolve. You don’t notice you’ve stopped calling your friends until months have passed. You don’t notice you’ve stopped feeling things until you’re sitting in an elevator next to someone in crisis and realize, with a jolt of recognition, that you have nothing left to offer.

You are balanced on a single leg. And the strangest part? From the outside, you still look fine. Productive, even. Impressive.

Guy described what happens inside that imbalance as numbness — and he was careful to say that we don’t numb selectively. We don’t get to turn off the stress and keep the joy. When we shut down to survive the grind, we shut down everything. The motivation. The connection. The small, quiet pleasures that make a life feel like yours.

We go on autopilot. And autopilot, it turns out, has no memory. You can spend years on it and look back to find almost nothing there.

The Hamster Wheel We Can’t See

Here is what I didn’t fully understand until this conversation: the grind doesn’t stay at the office.

It follows you home in the form of rumination — that involuntary, compulsive replaying of the difficult moment, the dismissive comment, the meeting that went sideways. Guy explained that rumination isn’t reflection. Reflection moves toward insight. Rumination just churns. It reactivates the original stress response — the cortisol, the tension, the unresolved feeling — without offering anything in return.

A two-minute conflict at work becomes two hours of suffering at home. And here is the part that stopped me: it’s contagious. When you carry that tension through your front door, the people who love you begin to absorb it. Partners of people experiencing burnout can develop symptoms themselves. The grind doesn’t just take you. It reaches for the people standing closest to you.

And still, we can’t simply decide to stop. That’s the cruelty of rumination. It’s involuntary. You can’t think your way out of it by telling yourself to think about something else.

What you can do is learn to ask one question when you notice the wheel spinning: What is the action item here? If there isn’t one, it’s not reflection. It’s rumination. And the only exit is to gently and deliberately redirect.

Playing to Win vs. Playing Not to Lose

One of the quieter insights from our conversation has stayed with me in the days since.

Guy talked about what researchers call challenge-threat theory — the idea that how you perceive a stressful moment changes your actual biology. Not metaphorically. Physiologically.

When you walk into a high-stakes meeting believing you are equipped for it, your body responds accordingly. The hormones that sharpen focus and support performance show up. You are playing to win.

When you walk in braced against failure — trying not to lose rather than trying to succeed — your body responds to that, too. You become tentative. You second-guess. The defensive posture, it turns out, predisposes you to the very outcome you were trying to avoid.

I think about how many of us move through our entire careers in threat mode without ever naming it. How much of what we call ambition is actually just a very sophisticated form of fear.

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What “Balance” Actually Means

We have been thinking about work-life balance wrong for a long time.

We treat it as an equation: if I add enough yoga and enough weekends, the hours at the desk become acceptable. But Guy’s point — and I think it’s an important one — is that the “life” in work-life balance isn’t a compensatory activity. It’s just life. Making dinner. Walking the dog. Sitting with your child while they do homework. Being present in the unremarkable moments that, accumulated over years, become the texture of a life well-lived.

You haven’t finished work when you close the laptop. You’ve finished when you stop thinking about it.

That distinction used to feel abstract to me. Now it feels like the whole thing.

The Line You Keep Moving

Most of us don’t fail to set boundaries because we don’t know we need them. We fail because we wait too long — until the resentment has already quietly built, until the yes we keep saying has hollowed something out.

Guy told me about people who finally draw a line, say the words carefully and clearly, and then assume the work is done. It isn’t. That’s the part nobody warns you about. The boundary isn’t the conversation. The boundary is everything that comes after — the patient, unglamorous repetition of holding it, again and again, without anger, without apology.

He called it a spoonful of sugar. Not because it’s sweet, but because the way you deliver a limit determines whether the other person can actually hear it. Most people aren’t trying to take more than you have. They’re just on their own autopilot, reaching for what was always available before.

What strikes me about this is how much it mirrors the grind itself. We don’t lose ourselves in one dramatic moment. We lose ourselves in the accumulated weight of every line we meant to draw and didn’t. Every time we answered the email at midnight. Every time we said I’m fine when we weren’t. Every small surrender that felt, in the moment, easier than the alternative.

The boundary isn’t a wall. It’s the practice of knowing where you end and the grind begins — and choosing, quietly and repeatedly, to stay on your own side of it.

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The Person in the Elevator

I keep coming back to Guy in that elevator. Not to judge him — the opposite, actually. Because there is something clarifying about watching someone who knows better get swallowed by the grind anyway.

It means the grind isn’t a character flaw. It isn’t a failure of discipline or self-awareness. It is a system — a powerful, culturally sanctioned system — that is very good at making its costs invisible until they show up somewhere you didn’t expect. In a sharp word. In an empty feeling. In the quiet realization that you’ve been so busy becoming successful that you forgot to remain yourself.

The question Guy’s story leaves me with isn’t how do I avoid burnout. It’s something more personal than that.

Which pillar has been quietly dissolving while you weren’t looking? Your health? Your curiosity? The simple capacity to be present in your own home, in your own life, with the people who chose you?

And what would it mean — not dramatically, not all at once — to begin rebuilding it?

Our full conversation in EP 767 of Passion Struck is linked below.

Download the FREE Companion Reflection Guide here.

Guy Winch’s new book, Mind Over Grind, is available now.

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Every 🧡, restack, or comment you share here on Substack

is like a signal flare…..

It helps this message find the person who is still walking

their own “schoolyard” alone.

Thank you for being part of this ecosystem.

I love turning these essays into a two-way conversation

So please let me know your thoughts below.

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© John R. Miles 2026. All rights reserved.

Imagine a pencil.

Not the plastic, mechanical kind, but a classic wooden one. In the mid-1840s, most American pencils were terrible—the lead was gritty, it broke constantly, and it smeared across the page.

In a small factory in Concord, Massachusetts, a young man was obsessed with fixing it. He spent months researching German chemistry and developing a new process for mixing clay and graphite, eventually creating the finest writing instrument in the United States.

You probably know his name, but you likely don’t know him as a manufacturing innovator. You know him as the “hermit” of Walden Pond.

For nearly two centuries, we’ve been told the story of Henry David Thoreau as a man who retreated from the world because he hated the hustle. We picture him sitting on a stump, staring at a chickadee, and ignoring his responsibilities. But as I discovered in a fascinating conversation with Ken Lizotte, author of Walden for Hire, we’ve been reading Thoreau all wrong.

Thoreau didn’t go to the woods to escape work. He went to redesign it.

When Thoreau wrote that “the mass of men lead lives of quiet desperation,” he wasn’t just being poetic. He was making a professional diagnosis.

He saw people trading the best years of their lives for things they didn’t need, trapped in a cycle of debt and performance. He realized that when we lose our connection to our own worth, we start living for a paycheck instead of a purpose.

In today’s language, Thoreau was undertaking a mattering project. He pioneered a model of ethical entrepreneurship—a way to build a livelihood that protects your soul rather than selling it.

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The Architect of a Life, Not Just a Living

Lizotte’s research reveals a Thoreau who was a “portfolio worker” long before the gig economy existed. He was a surveyor, teacher, lecturer, naturalist, and successful businessman.

But he did it all on his own terms.

He understood a truth we often forget: The price of anything is the amount of life you exchange for it.

Through Ken’s insights and our discussion on the Passion Struck podcast, three principles emerged for anyone feeling the weight of modern burnout. Let’s look at how Thoreau’s 19th-century “life design” can save our 21st-century sanity.

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1. Simplicity as a Competitive Advantage

Most people think simplicity is about deprivation. For Thoreau, it was about autonomy. By reducing what he called the “necessaries”—food, shelter, clothing—he lowered his overhead so much that he only had to work about six weeks a year to support himself.

The rest of his time? It was his own. He used it to write Walden, to study the environment, and to advocate for justice.

The Lesson: Where is your “cost of living” actually a “cost of freedom”? When you simplify your needs, you reclaim the power to say “no” to work that devalues you.

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2. Ethical Entrepreneurship: The 10-Day Rule

Thoreau once took a job as a teacher in a public school. On his tenth day, the school committee demanded that he use corporal punishment on his students. Thoreau refused. He didn’t wait for a better offer or stay “just for the experience.” He quit that afternoon.

He believed that your work should be an extension of your conscience. He ran his family’s pencil business with the same integrity, refusing to compromise on quality even when it would have been more profitable to do so.

The Lesson: A livelihood that requires self-betrayal isn’t a success; it’s a cage. Ethical entrepreneurship means choosing independence so you never have to choose between your paycheck and your principles.

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3. Walden as a Laboratory, Not an Escape

Walden Pond wasn’t a vacation; it was a controlled experiment. Thoreau wanted to see if a human being could feel inherently worthwhile without the noise of social status, debt, and constant “proving.”

He found that when you remove the performance, you find the person. He proved that you don’t need to “do more” to matter; you need to live in a way that allows you to feel that you already do.

The Lesson: We all need a “Walden”—a space where we confront the essential facts of our lives. It’s not about moving to the woods; it’s about moving toward your true self.

The Pivot: From Desperation to Disorientation

When Thoreau wrote that “the mass of men lead lives of quiet desperation,” he was diagnosing a 19th-century struggle with debt and industrial labor. But as I look at the world today, I see a slightly different, though equally painful, pattern.

I call it quiet disorientation.

It’s the feeling of moving at a hundred miles an hour while having no idea where you’re headed. It’s the ache of filling every silent gap in our day with digital noise—scrolling through feeds, checking metrics, responding to “urgent” pings—only to realize at the end of the week that you haven’t done a single thing that actually mattered to you.

We aren’t just desperate; we are lost in the glare of a hyper-connected world that has disconnected us from our inner compass.

This is where Ken Lizotte’s work on Thoreau becomes essential. Thoreau didn’t just want to “solve” desperation; he wanted to cure disorientation.

He went to the woods to “live deliberately,” which is the ultimate antidote to being disoriented. He wanted to find the “essential facts of life” so that he wouldn’t discover at the end of his life that he hadn’t lived it.

As Ken Lizotte said in our talk, “Henry’s message was: Breathe the air. Taste the fruit. Be attentive to the thing you are engaged in at this moment.”

I’m on this path, too—continually auditing my own life to see where “quiet desperation” is trying to creep in and where I can choose deliberate living instead.

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Which part of your life feels like it’s costing you too much “life”?

What is one thing you can simplify this week to reclaim your time and your worth?

I read every comment—let’s talk about how we can redesign our work to reflect our values.

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Listen to the full conversation with Ken Lizotte below:

The most dangerous skill in business today isn’t incompetence—it’s pretending.

We learn how to sound confident when we are uncertain, engaged when we are exhausted, and authentic in ways that still feel strategically safe. Over time, many workplaces begin rewarding emotional predictability more than honesty, and people slowly disconnect from parts of themselves in order to remain employable, promotable, or respected.

, Chief Heart Officer at VaynerMedia, believes organizations pay a significant price for that disconnection. As she told me,

“You can’t build a great company if people have to check their humanity at the door,” she told me.

And she’s got a point — one backed by both data and heart.

The most dangerous habit in business today is not incompetence. It is the quiet pressure to perform a version of yourself that feels acceptable, composed, and emotionally manageable to everyone around you.

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Why We Pretend at Work

What makes that observation compelling is that it is not simply philosophical. Research from Stanford psychologists Priyanka Carr and Gregory Walton found that teams with high psychological safety consistently outperform teams where people fear embarrassment, punishment, or social risk. When people feel safe enough to contribute honestly, collaborate openly, and admit uncertainty, performance improves alongside trust.

That creates an uncomfortable tension inside many modern workplaces. Companies often say they want innovation, creativity, and initiative, yet unintentionally create cultures where people spend enormous energy managing perception instead of engaging fully. The result is not just burnout. It is fragmentation. People begin separating who they are from how they show up professionally, and sustaining that division over time becomes emotionally expensive.

The deeper question is not whether professionalism matters. It does. The real question is whether professionalism has become confused with emotional concealment. If belonging at work depends on constant self-editing, people may succeed externally while becoming increasingly disconnected internally.

So perhaps the more important leadership challenge is not getting people to perform better, but creating environments where they no longer feel compelled to hide so much of themselves in order to belong.

What It Means to Lead from the Heart

did not begin her career trying to redefine leadership. Like many people navigating ambitious, high-pressure environments, she initially focused on proving she belonged. She worked hard, delivered results, and learned how to operate inside cultures that often rewarded toughness, certainty, and relentless performance. But beneath that success was a growing exhaustion that came from constantly managing the gap between professionalism and authenticity.

Advertising, especially at the highest levels, can reward sharp instincts and emotional control while leaving very little room for vulnerability or humanity. Over time, Claude began questioning the cost of that dynamic. After years inside those environments, she found herself asking a deceptively simple question: what happens to people when they spend most of their professional lives performing versions of themselves that feel emotionally sustainable to others but psychologically unsustainable to themselves?

That question eventually led to a pivotal conversation with
at VaynerMedia. Claude told him she no longer wanted to focus primarily on sales. She wanted to focus on the people doing the work — their emotional wellbeing, relationships, struggles, and growth. From that conversation emerged the role of Chief Heart Officer, a title that initially sounded unconventional in an industry built around metrics, competition, and scale.

What makes Claude’s work interesting is not the language of empathy itself, but the operational reality behind it. Her role is tied to retention, engagement, trust, communication, and long-term performance. She pays attention to the emotional atmosphere of the organization in the same way other executives monitor operational efficiency. In practice, that means listening carefully to what people are carrying beneath the surface of their performance.

What she discovered is something many organizations still underestimate: people rarely need more pressure than they are already placing on themselves. More often, they need environments where they can contribute honestly without feeling that their humanity is a professional liability. When people no longer spend so much energy protecting themselves emotionally, they tend to collaborate more openly, think more creatively, and remain more connected to the work they are doing.

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The Science of Being Yourself at Work

Claude’s work touches something deeper than morale or company culture. It speaks to a fundamental human need: mattering. Neuroscientists have found that social exclusion activates many of the same neural pathways associated with physical pain. The body often experiences rejection not as an abstract emotional event, but as a threat. That matters because most workplaces underestimate how much energy people spend monitoring whether they are accepted, respected, safe, or one mistake away from exclusion.

Many organizations unintentionally reinforce this insecurity through subtle but persistent signals about who belongs and who does not. Professionalism becomes associated with emotional restraint, certainty, composure, and constant performance. People quickly learn which parts of themselves are welcome and which are safer to conceal. Over time, that adaptation becomes exhausting because maintaining a sense of belonging starts to require continuous self-editing.

Claude describes this as “the silent tax of conformity.” What makes that phrase powerful is that the cost is rarely visible in a spreadsheet. It appears in diminished creativity, reduced honesty, guarded communication, and the gradual loss of emotional investment in the work itself. When people feel they must protect themselves socially, they become more cautious, less curious, and less willing to risk failure, disagreement, or vulnerability.

Her approach to leadership is not built around sentimentality. It is rooted in the understanding that emotional safety changes how people think, collaborate, and contribute. When individuals feel respected beyond their utility or output, they tend to engage more fully and take more meaningful risks. Innovation depends less on pressure than many companies assume. More often, it depends on whether people feel safe enough to bring their full intelligence, perspective, and humanity into the room.

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How to Lead from the Heart (Even If You’re Not a Boss)

You don’t need a title to lead with heart. Claude shares three habits anyone can adopt today:

1. Be emotionally brave.
   When something feels off, name it. Vulnerability builds trust faster than silence ever will.

2. Be emotionally optimistic.
   Don’t deny pain — reframe it. Ask, “What’s this here to teach me?”

3. Be emotionally efficient.
   Don’t get stuck in the drama of conflict. Get curious instead.

These habits form the blueprint for authentic leadership. They remind us that people don’t follow titles—they follow trust.

When I asked her what she looks for in a great leader, Claude didn’t hesitate:

“Someone who listens with their eyes. Someone who knows that love is the greatest performance enhancer in the world.”

That might sound soft, but the data backs her up. Gallup’s research shows that employees who feel genuinely cared for are 3x more engaged, 40% less likely to burn out, and far more likely to stay.

Heart-led leadership doesn’t just feel good—it works.

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What Happens When You’re Yourself

Being yourself at work feels risky—until you realize the real risk is pretending forever. Studies show that employees who feel forced to hide parts of themselves are 60% more likely to burn out and twice as likely to quit.

Claude’s message is simple: stop splitting yourself in two. Bring your humanity to work. When you do, you give others permission to do the same. And when people stop pretending, they start performing—not out of fear, but out of purpose.

What would change if you led one conversation this week with heart instead of habit?

Want to Lead (and Live) This Way?

For more, listen to my ad-free Passion Struck conversation with Claude Silver. It’s a powerful reminder that belonging isn’t built by policies—it’s built by presence.

Download the free companion Digital Workbook HERE!

One more thing: My upcoming children’s book, You Matter, Luma, is now available for pre-sale. It’s a story about kindness, courage, and the ripple effect of knowing you matter—lessons every adult at work could use, too.

When we lead from the heart, we don’t just change our jobs. We change each other.

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is like a signal flare…..

It helps this message find the person who is still walking

their own “schoolyard” alone.

Thank you for being part of this ecosystem.

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© John R. Miles 2026. All rights reserved.

In this heartfelt and empowering episode of Passion Struck, John R. Miles sits down with Jamie Kern Lima, self-made entrepreneur and founder of IT Cosmetics, to unpack the deeper truth behind her billion-dollar journey—one rooted not in luck or strategy alone, but in authenticity, resilience, and unshakable self-worth.

From pitching her dream from her living room to standing under studio lights on QVC—bare-faced and vulnerable—Jamie’s story is a testament to what’s possible when you stop chasing approval and start living from your truth.

Together, they explore:

Read more

I’ve interviewed astronauts, Navy SEALs, billionaires, Olympians, and world-renowned scientists.

Many of them have achieved things that seem impossible from the outside.

But every so often, I meet someone whose story forces me to rethink one of my deepest assumptions about success.

Matt Higgins was one of those people.

Most people know Matt today as the vice chairman of the Miami Dolphins, a guest shark on Shark Tank, a Harvard Business School instructor, and the co-founder of RSE Ventures.

But that’s not where his story begins.

It begins with a young boy selling flowers on street corners in Queens, scraping gum off McDonald’s tables, sleeping on the floor, and desperately hoping someone would come save his family.

And then one day, he realized nobody was coming.

That realization changed everything.

Discover How to Build Real Significance

When Nobody Is Coming to Save You

What struck me most about Matt’s story wasn’t the adversity he endured. It was the psychological shift that followed.

Like many children growing up in difficult circumstances, Matt spent years believing that the solution to his problems would eventually arrive from somewhere outside himself. Perhaps it would come through a mentor, a teacher, an opportunity, or simply a change in fortune. The details mattered less than the underlying belief that someone or something would eventually alter the trajectory of his life.

When that expectation finally collapsed, it could have produced resignation. Instead, it produced agency.

What makes this story resonate so broadly is that most of us have our own version of waiting. We may not be waiting for rescue in the literal sense, but many people spend years waiting for the conditions that will finally allow them to become who they want to be. We wait for greater confidence before taking a risk, more certainty before making a decision, or the perfect timing before pursuing an opportunity. We tell ourselves that action will begin once enough variables fall into place.

Yet life rarely works that way. Many of the qualities we hope to acquire before acting—confidence, resilience, judgment, and self-belief—are developed through action itself. They are not prerequisites for growth. They are often its byproducts.

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Why We Wait Longer Than We Need To

One of the most persistent myths about successful people is that they possessed unusual certainty before making consequential decisions.

Looking backward, their choices seem obvious. Their paths appear coherent. Success creates the illusion that they somehow knew what would happen.

The reality is usually far messier.

When Matt decided to leave high school, earn a GED, and pursue college, most of the adults around him believed he was making a mistake. Their concerns were understandable. They were evaluating his decision through the lens of convention and probability. Matt was evaluating it through the lens of his own circumstances and aspirations.

This tension reveals something important about human behavior. The obstacle is often not a lack of information. It is our relationship with uncertainty.

We tend to assume that certainty creates action. More often, action creates certainty. Confidence develops through experience. Judgment emerges through decisions. Clarity is frequently discovered on the path rather than before it.

The longer we insist on certainty before moving forward, the longer we remain trapped in analysis, waiting for a future version of ourselves to feel ready.

The Hidden Purpose of a Backup Plan

The title of Matt’s book, Burn the Boats, draws from a familiar story. Destroy the ships. Remove the retreat. Eliminate the possibility of turning back.

Most people interpret this idea as a lesson in commitment. I think it is actually a lesson in identity.

When people cling to backup plans, they are not always protecting themselves from practical risk. Often, they are protecting themselves from emotional risk.

A backup plan can help avoid a more uncomfortable question: What if I commit fully and still fail?

That question carries weight because failure is rarely experienced as a neutral event. It often becomes intertwined with self-worth. A failed business can feel like evidence that we are not capable enough. A rejected manuscript can feel like proof that we lack talent. A career setback can become a referendum on our value.

Under those conditions, hesitation feels reasonable.

The challenge is that the same mechanisms designed to protect us can also prevent us from fully engaging with opportunities that matter most. Sometimes the boats we need to burn are not physical alternatives. They are psychological escape routes.

Why Achievement Cannot Answer Questions of Worth

As I listened to Matt describe his journey, I found myself returning to a theme that has become central to my own work.

Many people spend years pursuing achievement in hopes that it will eventually provide something deeper than accomplishment. They hope it will offer reassurance.

Reassurance that they are valuable. Reassurance that they are enough. Reassurance that they matter.

Achievement can provide moments of validation. It can create opportunities, generate recognition, and confirm competence. What it cannot do is permanently resolve questions of significance.

This is why so many high achievers continue searching long after reaching goals they once believed would change everything.

The achievement delivers what it promised. It simply wasn’t promising the thing they truly needed.

The more I research and write about mattering, the more convinced I become that many forms of striving are attempts to answer questions that accomplishment alone cannot address. We want to know that our lives carry meaning. We want to know that our presence has weight. We want to know that we are valued not merely for what we produce, but for who we are.

Success can reinforce those feelings. It cannot create them from scratch.

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Why Growth Always Feels Like Uncertainty

One of the most compelling parts of my conversation with Matt involved his perspective on anxiety.

Modern culture often treats anxiety as something to eliminate. We search for strategies to reduce it, avoid it, or work around it.

Yet many of the most important experiences in life arrive wrapped in uncertainty.

Starting a business, writing a book, changing careers, entering a relationship, becoming a parent, stepping into leadership—none of these experiences provides guarantees.

Growth requires movement into territory where outcomes remain unknown.

This does not mean anxiety is always beneficial. It means that discomfort is not always a warning sign. Sometimes, it is evidence that we are operating at the edge of our current capabilities.

The challenge is not to eliminate uncertainty. The challenge is to develop enough trust in ourselves that uncertainty no longer prevents movement.

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What Matt Higgins Changed About My Thinking

Going into this conversation, I expected to hear insights about entrepreneurship, investing, and calculated risk.

What stayed with me afterward was something deeper.

Matt’s story is not ultimately about becoming fearless. It is about developing a relationship with yourself that can survive uncertainty.

People often assume courage comes from confidence in the outcome. More often, courage comes from confidence in your ability to respond regardless of the outcome.

That distinction changes everything.

When you trust yourself to adapt, learn, recover, and continue moving forward, uncertainty loses much of its power. The future becomes less about predicting what will happen and more about believing you can meet whatever happens next.

Takeaways

Stop Waiting for Perfect Clarity

Many of life’s most important decisions become clearer through action than through analysis. Clarity is often a result of movement rather than a prerequisite for it.

Separate Worth from Outcomes

Achievement can validate competence, but it cannot determine value. The stronger the connection between self-worth and performance, the harder it becomes to make a meaningful commitment.

Examine Your Backup Plans

Some backup plans are practical. Others exist primarily to protect the ego from disappointment. Understanding the difference can reveal where fear is influencing decision-making.

Build Self-Trust

Confidence grows from evidence. Self-trust allows you to act before the evidence exists. It is one of the most important foundations for intentional living.

Teach Kids They Matter

Final Reflection

’ story begins with a young boy realizing nobody was coming to save him.

What makes the story meaningful is not that he eventually became successful. It is that he stopped waiting for some future circumstance, opportunity, or version of himself to provide the permission he needed to move forward.

That transition may be one of the defining challenges of adulthood.

At some point, each of us must decide whether we will continue waiting for certainty or accept responsibility for authorship. The future rarely arrives fully formed. More often, it is shaped through a series of decisions made before we feel completely ready.

The quality of our lives may depend less on eliminating uncertainty and more on learning to trust ourselves enough to move through it.

Check out the full conversation with Matt Higgins below:

Share The Ignited Life: Philosophical First Aid for Being Human

Thoughts? Let me know below this essay!

Every 🧡, restack, or comment you share here on Substack

is like a signal flare…..

It helps this message find the person who is still walking

their own “schoolyard” alone.

Thank you for being part of this ecosystem.

I love turning these essays into a two-way conversation

So please let me know your thoughts below.

Leave a comment

© John R. Miles 2026. All rights reserved.