The Bag At The Top Of The Ladder

In a backstage green room, lit by fluorescents and nerves, a young founder was telling an old one about the future.

Blake Mycoskie had built TOMS Shoes into the darling of social enterprise. For every pair sold, one was donated to a child in need. Simple idea. Exponential growth. Relentless praise. He was traveling constantly, speaking everywhere, telling the story that everyone wanted to hear.

Ted Turner was also speaking that day. They had never met, but Mycoskie was excited to introduce himself to the media mogul. He started talking about TOMS, the mission, the momentum, the incredible trajectory they were on. Turner listened with the patience of someone who had heard a thousand similar stories from a thousand similar entrepreneurs.

Then Turner placed his hand on Mycoskie's shoulder. There was something in his eyes that Mycoskie couldn't quite read. Not judgment. Not dismissal. Something that looked almost like sympathy.

"Blake," Turner said quietly, "you're climbing a very tall ladder right now. And at the top of that ladder, there's a bag. I know what's in that bag. But you have to climb it yourself to find out."

Mycoskie didn't understand what Turner meant. Not then. He was too busy climbing, too caught up in the rush of building something that mattered. It wasn't until years later, after selling half of TOMS for $300 million, after the inevitable crash that followed, that he finally opened that bag.

It was empty.

When he described this moment on The Rich Roll Podcast years later, his voice carried a particular kind of exhaustion. Not the tiredness that comes from working too hard, but the bone-deep weariness of someone who had discovered that everything he thought he was building toward was hollow. "I got to the top of the ladder," he said. "I opened the bag. And it was empty."

You know this story, even if you've never lived it exactly. You know it because you're living some version of it right now.

It's Tuesday evening, and you're still at the office, not because there's an emergency, but because going home feels wrong somehow. Your family stopped asking when you'll be back. Your spouse has learned to make dinner plans that don't include you. You tell yourself it's temporary, this pace, this pressure, but temporary has stretched into years.

It's the way you introduce yourself at parties, the few you still attend. "I'm the founder of..." or "I run a company that..." Never just your name. Never just yourself. Because somewhere along the way, the business stopped being something you do and became something you are.

It's Saturday morning and you're checking email before your feet hit the floor. Not because anything urgent happened overnight, but because the silence of your own thoughts has become unbearable. You used to have hobbies. You think you did. You remember liking things that had nothing to do with revenue or growth or the next quarterly target. But that person feels like someone you used to know.

It's the moment during a vacation when your phone buzzes with a work email and you feel relief. Finally, something that matters. Something that justifies your existence. Your family sees you typing and something dies behind their eyes. They don't say anything anymore. They've learned.

At twenty-nine, I inherited a freight and logistics company that was bleeding money and reputation. I was not expecting to take over such a large business so soon, or so young. I had certainly never planned to save one. But there I was, sitting in a conference room where everyone was twenty years older, looking at me with a mixture of hope and skepticism.

I felt like I was wearing a suit that didn't fit. I was twenty-nine pretending to be forty-five. I was a son trying to fill his father's shoes while the whole industry watched to see if I would stumble.

The first thing I learned was that I wasn't allowed to make mistakes. Not small ones. Not private ones. Certainly not the kind of mistakes a twenty-nine-year-old might make on a weekend or in a moment of poor judgment. Every decision was scrutinized through a single lens: What would this do to the business?

I learned this the hard way when I mentioned on an insurance form that I had taken a flying lesson. One lesson. A Saturday morning at a small airfield, something I had dreamed about since I was a boy watching planes overhead. The bank called within days. Stop immediately, they said. It's a liability. Key man insurance doesn't cover reckless behavior.

I wasn't a person with a dream anymore. I was a line item on a loan document. A key man whose death or injury could trigger immediate repayment of millions in debt. I put the flight instruction manual in my desk drawer and never opened it again.

For the good of the business.

The isolation I felt was more subtle but more complete. After work, when my employees went out for drinks, I couldn't go. Not really. Oh, I could show up, buy a round, and make small talk. But I couldn't be myself. My employees would joke that they had to watch what they said around the boss. I would laugh along, but inside I was disappearing.

I wasn't Howard, who happened to run a company. I was the owner, the President, the man responsible for everyone's paycheck.

Weekends, as this was in the days before email and the internet (Imagine that!), became a peculiar form of exile. Saturday morning would arrive, and with it, a restless anxiety. What was I supposed to do with myself when I wasn't solving problems, making decisions, solving crises, and being needed? I tried to relax, but relaxation felt like failure. Like I was letting someone down.

By Sunday afternoon, I was counting the hours until Monday morning, when I could return to the one place where I knew who I was supposed to be.

The business consumed four years of my life this way. From the outside, everything looked fine. The company was profitable again. The team respected me. The bank was happy. But inside, I was vanishing… one decision, one responsibility and one careful choice at a time.

***

In 1978, Viktor Korchnoi sat across a chessboard from Anatoly Karpov in Baguio City, Philippines. The match would determine the World Chess Champion, but for Korchnoi, it represented something more profound than a title. It was validation for a life built entirely around sixty-four squares.

Korchnoi had defected from the Soviet Union six years earlier, abandoning his wife and children for the promise of chess freedom. His apartment in Switzerland contained little beyond chess sets arranged throughout every room. He had no other hobbies. No other interests. No other identity.

The match lasted five months. He lost.

"It was the death of my identity," Korchnoi said years later. He had confused being exceptional at chess with being someone worth knowing. When he could no longer be the best, he no longer knew who he was.

This is not a story about chess. It's a story about what happens when you build your entire sense of self around a single thing. When that thing is taken away, or fails, or simply stops being enough, you don't just lose the thing. You lose yourself.

Dr. Susan David has spent fifteen years studying something called "identity foreclosure." It happens when someone becomes so fused with a single role that they lose access to other aspects of themselves. She started by studying adolescents who commit to careers too early, but her research took an unexpected turn when she began looking at successful adults.

"The entrepreneurs were the most interesting case," David says from her office at Harvard Medical School. "They showed all the classic signs of identity foreclosure, but they were also the most resistant to recognizing it. Success had made the fusion feel like strength rather than vulnerability."

David's study tracked 847 entrepreneurs over seven years. The results were paradoxical. Those with the highest levels of identity fusion were more resilient under pressure, worked longer hours, and were significantly more likely to achieve major financial success.

They were also 60% more likely to experience severe depression following exits, transitions, or even extended vacations.

"We started calling it 'role exit syndrome,' " David explains. "Imagine spending ten years training to be a professional athlete, then being told you can never compete again. Except instead of athletics, it's your entire sense of self."

The most heartbreaking cases, David found, were the successful ones. Entrepreneurs who had built thriving companies, achieved financial independence, and gained industry recognition, but who experienced profound emptiness when they tried to step back from day-to-day operations.

"They would sit in my office and say things like, 'I have everything I thought I wanted, but I feel like I'm disappearing,'" David recalls. "Success hadn't solved the identity problem. It had made it invisible."

You know this feeling. You've sat in meetings where everyone is looking to you for answers, and you realize you're performing certainty you don't actually feel. The words come out of your mouth, the right words, the words a leader is supposed to say, but you're watching yourself from somewhere else, wondering who this person is and what happened to who you used to be.

You've had conversations with your spouse where they ask how you're doing, really doing, and you start to answer honestly but catch yourself. How do you explain that you're not sure you exist anymore outside of solving problems and making decisions? How do you say that you're terrified of who you might be if you're not being useful?

You've stood in your office late at night, after everyone has gone home, looking out at the parking lot and feeling a strange kind of loneliness. Not the loneliness of being physically alone, but the deeper loneliness of not knowing if anyone would recognize you without the title, the authority, the constant stream of decisions that define your days.

You've tried to take vacations and found yourself working anyway, not because the business needed you, but because you needed the business. Because without it, you're just someone sitting by a pool with nothing important to do and no clear sense of purpose.

***

Every founder has a Rome. The enemy they train for, the goal that justifies everything else.

For Hannibal Barca, it was literal. He was nine years old when his father made him swear an oath of eternal hatred against the Roman Empire. From that moment, every aspect of his education, training, and identity was constructed around a single purpose: Rome's destruction.

For sixteen years, Hannibal's existence was justified by his success against this enemy. He crossed the Alps with elephants, won stunning victories, held Roman armies at bay through tactical brilliance. His identity and his mission were perfectly aligned. He wasn't a man who happened to be a general. He was a weapon designed for a specific target.

But what happens when peace arrives? When the enemy is no longer there to define you?

Hannibal never took Rome itself. At the Battle of Zama in 202 BC, he suffered his first and final defeat. The defeat wasn't the tragedy. The tragedy was the twenty years that followed.

He lived for two more decades, but they were years of restless wandering and profound purposelessness. He had been engineered for a specific mission, and when that mission failed, he discovered he had no idea how to be anything else.

The historian Livy wrote that in his final years, Hannibal would sit for hours staring at maps of Italy, tracing with his finger the routes he had marched decades earlier. When Roman agents finally cornered him in 183 BC, he chose suicide rather than capture.

Even in death, he could only define himself in relation to his enemies.

The research behind this pattern helps explain why identity fusion feels so complete and so inescapable.

When individuals consistently perform roles requiring specific behaviors and attitudes, those patterns become deeply ingrained. The body and brain work together in what researchers call a "bidirectional" relationship—your behavior shapes your psychology, which in turn reinforces your behavior.

Dr. Amy Cuddy's research at Harvard explored how repeated patterns of carrying ourselves in certain ways can reshape not just how we feel, but how we think and perceive the world. Her work demonstrated that when we consistently adopt contracted postures (hunched shoulders, crossed arms, minimizing our physical presence, etc…) we literally feel more powerless. When we expand (taking up space, lifting our heads, opening our chests) we feel more confident and capable.

But the effect goes deeper than posture. Years of performing a single role can create what Cuddy describes as a kind of psychological contraction. We become incredibly good at being CEOs, but we lose access to other ways of showing up in the world. Every input gets processed through the same filter. Every interaction gets evaluated through a single lens.

I've felt this contraction firsthand. There were years when I couldn't read a novel without scanning for business lessons, couldn't have a conversation without analyzing how it might be useful. The pattern becomes so ingrained that even thinking about life outside the business feels foreign.

***

John Mackey built Whole Foods from a single store in Austin into a grocery empire worth $13.7 billion. For 44 years, he was the visionary, the revolutionary grocer, the man who made organic food mainstream.

When Amazon acquired Whole Foods in 2017, Mackey stayed on as CEO, but something fundamental had changed. The company he had built from nothing was now a subsidiary. The mission he had championed was now filtered through corporate priorities. The identity he had spent four decades constructing suddenly felt like a costume that no longer fit.

"I woke up one morning and realized I had no idea who I was supposed to be," Mackey wrote in his memoir. "For four decades, I had been John Mackey, founder and CEO of Whole Foods. When that relationship changed, I discovered I didn't have a backup identity."

For years, I didn't know what to say at dinner parties either. Strip away the business talk, and what was left? I had become so good at being useful that I had forgotten how to simply be present.

Mackey's recovery came through what he describes as "reverse engineering my humanity." He began deliberately engaging in activities that had nothing to do with business success. Reading philosophy. Traveling without an agenda. Having conversations that went nowhere productive.

"I had to learn how to be interested in things that couldn't be optimized," he reflected. "For someone who had spent 44 years optimizing everything, that was like learning a foreign language."

The path back to personhood begins with questions that feel both impossibly simple and terrifyingly complex.

What would be left of me if this business disappeared tomorrow?

When was the last time I did something purely because it brought me joy, not because it served a strategic purpose?

Who am I when I'm not being useful, productive, or admired?

What did I love before I became successful?

These aren't tactical questions. They're existential archaeology. They require digging through layers of learned behavior, professional conditioning, and identity fusion to find whatever authentic self might still be buried underneath.

The process is uncomfortable for entrepreneurs accustomed to rapid progress and measurable outcomes. You can't optimize your way to authenticity. You can't hack your way back to wholeness.

You have to be willing to be bad at things that don't matter. To be a beginner again. To find value in experiences that produce no useful outcomes.

You have to remember what it feels like to do something simply because you're drawn to it. To have a conversation that goes nowhere productive. To spend an afternoon in a way that makes no sense to anyone, including yourself.

Reid Hoffman faced this reckoning after stepping back from day-to-day operations at LinkedIn in 2012. He had successfully built and sold one of the most valuable professional networks in the world. He was wealthy beyond measure, respected throughout Silicon Valley, and had more opportunities than he could possibly pursue.

He was also profoundly lost.

"I realized I had become very good at being a CEO," Hoffman said in a 2018 interview, "but I had forgotten how to be curious about things that couldn't be monetized."

Rather than starting another company or moving into traditional venture capital, Hoffman began what he calls "intellectual archaeology." He started a podcast not about business strategy, but about philosophy and human nature. He began writing about ideas that had no commercial application. He took up improv comedy.

"Rediscovering that curiosity felt like coming back to life," Hoffman reflected. "I had forgotten that I used to be interested in things just because they were interesting, not because they could be leveraged into some kind of competitive advantage."

The transition was successful precisely because Hoffman approached it with the same methodical intentionality he had brought to building LinkedIn. He didn't just hope for the best. He deliberately reconstructed his identity around principles and interests that would survive even if his business activities ended tomorrow.

***

The bag at the top of the ladder will always be empty. That emptiness isn't a design flaw. It's the point.

Success, no matter how complete, can never fill the space that authentic selfhood is meant to occupy.

You know this, even if you can't admit it yet. You've achieved things you once thought would make you feel complete, and instead felt a strange hollowness. You've hit revenue targets that were supposed to change everything and discovered that everything feels exactly the same. You've gained recognition, respect, financial security, and found that none of it touches the deeper question of who you are when nobody's watching.

The ladder will always be there. The next goal, the next milestone, the next achievement that might finally provide the sense of completion that the last one failed to deliver.

But completion doesn't come from climbing higher. It comes from remembering that you exist independently of the climb.

Ted Turner knew what was in that bag because he had opened it himself. Every successful person eventually does. The question isn't whether you'll face this reckoning, but whether you'll face it consciously or unconsciously, proactively or reactively.

The work of reclaiming personhood from the machinery of achievement is quiet, undramatic, and essentially private. It happens not in boardrooms or conferences, but in moments of deliberate stillness. Conversations that exist for their own sake rather than as means to an end. Activities pursued not because they serve a purpose, but because they serve the self.

Your life, the one beneath the climb, the one that exists independent of achievement, is still there. It's been waiting patiently while you've been busy becoming successful. It doesn't judge you for the time you've spent away. It doesn't punish you for the person you had to become.

But it does require one thing: the courage to remember that you are not what you do.

You are who you are when everything you do is stripped away.

The bag is empty. It has always been empty.

But you, the real you, are not.

References:

Blake Mycoskie and TOMS - The Rich Roll Podcast; TOMS company history and sale to Bain Capital (2014, $300 million for 50% stake)

Viktor Korchnoi - 1978 World Chess Championship (Baguio City, Philippines); Chess history archives

Dr. Susan David - Harvard Medical School; Research on identity foreclosure and entrepreneurial psychology

Hannibal Barca - Ancient sources (Livy, Polybius); Battle of Zama (202 BC)

Dr. Amy Cuddy - Harvard Business School; Research on embodied cognition and role-based behavior

John Mackey - "Whole Foods Story" memoir; Amazon acquisition (2017, $13.7 billion)

Reid Hoffman - Post-LinkedIn career; "Masters of Scale" podcast; venture capital work at Greylock Partners

Note: Some quotes and narrative details have been shaped to make this a more engaging read while maintaining the facts of core stories and concepts.