Most of us are optimizing for the wrong thing.

Last week I wrote about running the Chicago Marathon on a fractured tibia. The experience was a deep learning moment, but the real insight came after → Not stopping.

Any reasonable person would have called it and found a different hobby. I didn’t. Not out of toughness. Not because I loved running that much. I just kept not dying.

And that was the whole secret to becoming a professional marathon runner later.

If you want to run a sub-3 marathon, you don’t need a perfect training plan. You don’t need the best shoes or a Strava coach. You need to not die. Don’t get a catastrophic injury. Don’t lose motivation. Don’t get distracted chasing three different goals at once.

Don’t die for two or three years, and I guarantee you can qualify for Boston or any other race that matters.

Most runners never find out because they don’t survive long enough to see it.

When It Gets Real

A few weeks ago, at a leadership offsite, Ricardo Amper, the founder of Incode (an AI-powered identity unicorn), said something that stayed with me.

The startup game is like musical chairs. The music plays. Everyone’s moving. It stops, and there are fewer chairs than people. If you are left standing, you’re out. Doesn’t matter how smart you are. If the fundraising window closes without you, the game is over.

His point wasn’t about winning in the short term. It was about always having a chair and having one more chance.

The founders who survive multiple funding cycles, multiple downturns, multiple moments where the company almost didn’t make it, they’re not always the smartest in the room. They’re the cockroaches that don’t die.

The ones who quit in year two never find out what year four would have looked like.

Most founders optimize for growth. For the metrics that look good in a pitch. The real optimization target is survival. Infinite survival. Don’t die. The rest figures itself out.

Lesson Learned: Survival isn’t the consolation prize. It’s the strategy. Compounding only works if you’re still there when it kicks in.

Worth Your Time

Paul Graham published an essay simply titled “How Not to Die.” He wrote it for YC founders but it reads like a running manifesto. His argument: most startups that fail didn’t get beaten. They just stopped. If you solve the problem of not dying, everything else becomes a question of time.

In 2019 I was rolling through downtown Chicago in a wheelchair after the Marathon with a fractured tibia. Three years later, I ran a 2:38 in Boston. The only thing that happened in between was not dying.

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The doctor looked at the MRI like he’d seen this before.

“Well, my friend, you ran a marathon with a fractured tibia bone.”

I’d just finished the Chicago Marathon. All 26.2 miles of it. On a broken leg. I didn’t know it was broken until I was lying in a hospital bed in North Chicago, staring at the ceiling while the room smelled like antiseptic and humiliation.

My coach called while I was still in the bed. Wong Way Sile, not your standard running coach. Two-time NYC Marathon winner.

I expected sympathy. I got something else.

He told me about the time he was leading the NYC Marathon with five miles to go and dropped out. Exhausted. A man who won that race, walking off the course.

Then he said it: “It wasn’t until I learned to run slow that I became fast.”

I was too frustrated. I was lying in a hospital bed with a broken bone in my leg, and he was giving me philosophy.

It took me years to understand what he meant.

The problem wasn’t my training volume. It wasn’t my ambition. The problem was that I treated every single session like a race: crushing easy days, moderate days, all of it. Every run was at the same grinding, semi-hard effort. I thought that was toughness.

It wasn’t. It was just noise.

What I was doing, I’d later learn, is exactly what breaks most runners. Sports scientist Dr. Stephen Seiler spent years studying how elite endurance athletes actually train. He found that world-class runners, cyclists, and skiers from completely different countries and cultures had all converged on the same pattern: around 80% of training at genuinely easy effort, the other 20% brutally hard. GOREWEAR Nothing in the murky middle.

I was living in the murky middle. When recovery runs are too fast, instead of returning to full capacity you might recover to only 80–85%. So when it’s time to go hard, your body is already starting in a hole. Marathon Handbook

That’s what happened in Chicago. I showed up to the start line already depleted — from months of training that was never actually easy.

The tibia didn’t lie.

Three years later, I stood in Hopkinton. Boston. And I ran 2:38.

The difference wasn’t more intensity. It was finally understood where the intensity belonged.

When It Gets Real

Most founders I know run their companies exactly the way I ran training in 2015, I was certainly one of them.

Every day is a sprint. Every week is a crisis. Every meeting has the same urgency. We’re in the murky middle constantly, working hard enough to be exhausted, never hard enough to break through.

I’ve watched brilliant people plateau not because they lacked ambition, but because they couldn’t distinguish between signal and noise. They were going hard on everything, hiring decisions, product strategy, investor calls, ops reviews, and as a result they were going hard on nothing.

Reed Hastings has talked about Netflix’s approach to decision-making in similar terms: not everything deserves the same level of energy. The moves that matter, a market entry, a key hire, a pivot, deserve your full capacity. That requires everything else to be genuinely easy.

Easy days in business aren’t lazy days. They’re recovery.

If you’re exhausted all the time, you’re probably not working too little. You’re probably running easy days unnecessarily hard.

Lesson Learned: Sustainable performance, in running and in business, requires the discipline to go easy when the moment doesn’t demand hard. Most people don’t lack intensity. They lack distribution.

Worth Your Time

80/20 Running by Matt Fitzgerald. The book that pulled Dr. Seiler’s research out of the lab and into training plans. It’s written for runners but the logic maps directly to how you allocate energy across anything that requires sustained performance. The core idea, most of your effort should be genuinely easy, so the 20% that matters can actually land, will change the way you look at your calendar.

Thirty-eight months after Chicago, I crossed the Boston finish line in 2:38.

I thought about Wong Way Sile’s words a lot on that course. Especially around mile twenty-two, when the runners around me were starting to crack and I had something left.

That’s what slow builds.

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Mile 128 of the Sahara Desert ultramarathon.

My feet have been numb since mile 62. The sun has cooked through my buff, and I can feel it on my skull. I’ve got three liters of water left, no shade for the next 11 kilometers, and my legs are having a conversation with my brain that I don’t want to be a part of.

This is the moment when no pump-up song can bring your motivation back.

Lady Gaga or Bad Bunny won’t fix this. Neither is a power gel, caffeine, or anything else in the biology playbook. At this level of depletion, the body has stopped listening to hacks. The only thing left is something deeper, the one item the body will not find, but the mind can.

A few years ago, I saw a podcast that featured Luis Alvarez, a businessman, adventurer, and a man who treats life like it’s running out. One of his feats: five Ironmans, five days, five continents.

But it’s his Mt. Everest ascent that stayed with me.

After reaching the summit, his goggles fogged on the way down. At minus 50 degrees Fahrenheit, the condensation froze solid on the lenses. He switched to his spares. Same result. The descent was technical, exposed, and nearly vertical in sections. He kept moving without them.

By Camp IV, at 8,300 meters, still in the death zone, he had gone blind for not having worn eye protection. His corneas had burned.

What kept him moving?

Not willpower. Not a mantra. No caffeine shot.

One thought, simple yet infinitely powerful: If I die here, my son will carry the burden of having sent me to my death.

When Luis asked for it, his son gave his dad his blessing to embark on the expedition. The boy was only 15, and Mr. Alvarez could not live with the burden of thinking his son would feel guilty of his father’s death

That thought, that single, specific, non-negotiable thought, pulled him off the mountain alive.

It is much easier to let oneself down than to let a loved one down.

When It Gets Real

An old and wise marathon coach taught me this technique. Deep, motivating mind visualizations. He called them Power Thoughts.

A Power Thought is the one idea that survives even in the darkest moments. It connects to something outside yourself, a person you refuse to let down, a commitment you made before the odds got long, a version of the future you owe someone else.

“When nothing else works,” he used to say.

A few weeks before any major race, I choose five. I write them on my left forearm in permanent marker. After dozens of miles into a race, my head sometimes won’t work properly, so I need them to be visible.

What is interesting is that the best Founders deploy the same system.

Howard Schultz, founder of Starbucks, grew up in a Brooklyn housing project. His father drove a truck. When Schultz was seven, his father broke his ankle on a delivery and was fired. No insurance. No plan.

Schultz never forgot the look of a man made helpless.

That image became his anchor; it became his Power Thought. Every time Starbucks hit a wall, he says he came back to one thought: his helpless father and the people in his stores, who cannot end up like him.

In 2008, during a crisis, the share price was down 42%, stores were closing, and the board was demanding cuts. Schultz returned as CEO and, on day one, canceled a $20 billion stock buyback to reinvest in employees instead, a very tough decision at the time. Analysts called it reckless, but it was the single most important factor in turning the company around.

He didn’t calculate it. When nothing else was working, he returned to the one thought that outranked everything else.

That’s the success cheat. You don’t eliminate the hard thing. You use it to have something truly worth bleeding for.

Lesson Learned:

When willpower runs out, motivation takes over. But motivation only works when you have something worth fighting for.

Worth Your Time

The Comfort Crisis by Michael Easter. Easter’s argument is simple and uncomfortable: modern life has systematically removed the conditions under which mental strength is built. He documents what happens physiologically and psychologically when people deliberately seek discomfort — and why that exposure produces exactly the kind of resilience Power Thoughts tap into. Directly relevant to anyone who wants to build the mental infrastructure before they need it.

Have a great week.

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4:55am. The alarm on my watch vibrates against the nightstand.

The room is still dark. My eyes don’t open right away. As I pull the blanket back, I feel the cold morning air touch my skin.

Then I hear it.

Subtle, but clear. Drops against the window.

And the dialogue starts: It’s raining. I shouldn’t run in the rain. What if I slip? What if I catch a cold? I’ll make it up tomorrow.

The blanket is right there. Warm. Forgiving.

Most runners pull it back up. Relieved. But somewhere deep down, we all know we could’ve gone out.

Deep in my 2019 Boston Marathon prep, I trained at a track in the heart of Mexico City. On normal mornings, the place was buzzing — sixty, eighty runners grinding intervals, watches beeping, music speakers, everyone talking.

On rainy days, I’d arrive at the track at 5:15 am to total silence.

In the dark of the morning, only a couple of maniacs would be at it. You could see the splash of each step from afar. No music. No small talk. Just rain, and two people who had decided that this morning (like any other) was not optional.

Something became instantly clear that had been impossible to see on dry days: who was completely committed. Not enjoying themselves but, irreversibly, dangerously focused to reaching their goal.

These were the runners to watch out for. Not the ones with the cool Instagram Stories in Spring. The ones who showed up in the rain of August.

Rainy days revealed what dry weather made impossible to see.

The Business Version

In business, rainy days are a gift, not because it’s pouring on you, but because you finally get to see who is truly self-motivated and who was just waiting for a good excuse.

The problem is that business doesn’t hand you the filter as cleanly as running does. People have polished resumes, sharp answers, and a story for every room. On a dry day, almost everyone looks capable.

Then the storm hits. The funding round collapses. The key customer is about to walk. The product breaks at the worst moment. And that’s when the line gets drawn. The rainmakers, the ones who refuse to pull the blanket back up, come into the light. The rest, the rain avoiders, seek shelter and vanish.

Lesson Learned: Anyone can perform on a dry track. The filter only works when the weather turns.

Worth Your Time

In April 2018, Yuki Kawauchi — a Japanese office clerk who ran marathons on weekends with no sponsor and no coach — won the Boston Marathon in the worst conditions in decades. Driving rain, strong headwinds, temperatures just above freezing. The favorites, built for perfect days, collapsed one by one. When asked about the weather, he said: "For me, these are the best conditions possible." Some people only perform when everything is right. A few others only reveal themselves when nothing is. Watch here →

I still don't have a perfect system for spotting rainmakers before the storm. I've been fooled more than once. But I've started paying less attention to what people do in the good weeks and pay very close attention to what happens on faul weather.

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Last year, I was sleeping in the middle of the Sahara Desert when an unexpected sandstorm blew our tent away.

Ours and about 200 others.

We were running the Marathon Des Sables, a 250km race across the Sahara, famously dubbed the toughest foot race on earth.

Our team, along with roughly 100 others, had to scramble in the middle of the night to retrieve the tents, drag them back, and re-anchor them against the howling north winds.

By the time everything was secured, we had maybe three hours of sleep before the next morning’s 100km stage.

An authentic nightmare.

But what stayed with me wasn’t the ferocity of the storm.

It wasn’t waking up in a sleeping bag full of sand.

It was something subtler:

The near-total absence of complaining the next morning.

That night reminded me of something I’d read in The Rise of Ultra Runners, one of the best running books I’ve come across since Born to Run.

Adharanand Finn, the author, describes arriving at his very first ultra race, only to be blindsided by a logistics delay that forced the entire group to sleep in the airport.

He was furious.

“What kind of organization is this? Is this what we paid for?”

He vented loudly.

Meanwhile, the dozen seasoned ultra runners around him quietly grabbed a patch of floor, closed their eyes, and went to sleep.

Later in the book, after dozens of ultras under his belt, he looks back on that airport night with embarrassment.

He finally understood what the others already knew:

Play the cards you’re dealt, keep moving, and don’t waste energy on complaining.

The Business Version

A colleague asked me recently what single trait I look for most when hiring.

I didn’t hesitate.

People who don’t complain.

But the best ones go even further than that.

They’re not just indifferent to adversity.

They’re genuinely grateful for it.

When the sandstorm hit at 2am in the Sahara, the veterans in the camp weren’t just tolerating it.

Some of them were almost smiling.

Because they already knew what the rest of us were still learning:

That’s the race. The hardship isn’t a detour from the experience. It IS the experience.

The best founders carry that same mentality.

When a deal collapses, when a key hire walks out, when the product breaks in front of a customer, there’s no victim story. No “why does this always happen to us.”

Just: what do we do in the next five minutes?

And here’s why it matters beyond mindset:

If your instinct in hard moments is to complain, to your team, to yourself, even just inside your own head, you are burning the one resource you cannot replenish:

Energy.

Because while you’re explaining why the storm wasn’t your fault, someone else is already re-anchoring their tent.

Why Complaining Is So Expensive

Most people underestimate the cost of complaining.

It’s not just the time spent venting.

It’s what happens to the room.

One complainer drains the energy of an entire team. They introduce doubt. They slow decisions. They make hard moments feel harder than they already are.

The best operators compress the reaction time between “something went wrong” and “here’s what we’re doing about it.”

That compression is one of the most valuable skills a founder or operator can have.

Charlie Munger put it better than anyone:

“I have a theory that the dumbest thing you can do in life is feel like a victim. Even if you are a victim, I think it’s a mistake.”

Lesson Learned:

The real test isn’t how someone performs when everything goes to plan.

It’s what they do when the sandstorm hits at 2am.

3-2-1 Sprint

3 Ideas

1. Compress the reaction gap. The time between “something went wrong” and “here’s what we’re doing” is a skill you can train.

2. Audit your energy leaks. Look in the mirror and identify when you are complaining.

3. Play the cards you’re dealt. The storm doesn’t care about your plan. Neither does the market.

2 Quotes I

“I have a theory that the dumbest thing you can do in life is feel like a victim. Even if you are a victim, I think it’s a mistake.” Charlie Munger

“It is not the strongest or most intelligent who survive, but those most adaptable to change.” Charles Darwin

Final Thoughts

Most people think resilience is about toughness.

It’s not.

It’s about how fast you can accept what happened, stop explaining why it’s unfair, and get back to work.

The runners in the Sahara weren’t tougher than everyone else.

They just knew the faster they dealt with the soprano, the sooner they would be sleeping.

That’s the real skill.

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A Harvard professor once wrote something that sounds completely ridiculous:

100% is easier than 98%.

How could doing something all the time possibly be easier than doing it almost all the time?

Yet the more I think about it, the more I realize this rule quietly explains discipline, entrepreneurship, and marathon running.

I discovered this lesson the hard way while trying to break the 3-hour marathon barrier.

And strangely enough, it had nothing to do with running and everything to do with human weakness.

In marathon running, every runner usually has a unique edge.

Some are built stronger.
Some have better speed.
Some have superior endurance.

For me, my competitive edge has always been something much simpler:

Getting extremely lean before races.

In a marathon, carrying less weight over 26.2 miles pays off big time.

When I’m training seriously, I’ll drop my body fat from around 15% to the 3% range.

For many years, I could never break below 10% body fat.

Until I came across a concept from Clayton Christensen’s book How Will You Measure Your Life.

In the book he writes:

“It’s easier to hold your principles 100% of the time than 98% of the time.”

It sounds counterintuitive.

But it’s true.

So one day, while preparing for my second attempt at breaking the 3-hour marathon at the Marine Corps Washington Marathon, I decided to apply the rule to my diet.

I cut out alcohol, processed sugar, and low-quality carbs.

Not 98%.

100%.

At the beginning it was brutal.

Especially the alcohol part.

Every time I went out with friends someone would offer a beer or a glass of wine.

“Come on, just one. How bad can it be?”

But I stuck to the rule.

And something strange happened.

After a few weeks the temptation disappeared.

No debate.
No negotiation.

Just a habit.

Suddenly it was easy.

No joke: 100% became easier than 98%.

When people see that level of discipline, they assume it must take enormous willpower.

The truth is the opposite.

I do it precisely because I don’t trust my willpower.

Once the rule is absolute, the decision disappears.

The Business Version

This rule shows up everywhere in business.

Founders often try to operate at 98% commitment.

They launch a startup… but keep the safe job.

They say they want to build a great company… but still optimize for comfort.

That silent negotiation slowly kills the dream.

The most effective founders I know operate in absolutes.

They remove ambiguity.

No backup plan.
No hedging.
No “let’s see how this goes.”

Just:

We’re doing this.

Ironically, that level of commitment simplifies everything.

Decisions become clearer.
Priorities sharpen.
Energy concentrates.

Once the boats are burned, the path forward becomes obvious.

In a 60 Minutes interview Elon Musk gave perhaps the simplest founder philosophy ever:

“I don´t ever give up.”

That’s the 100% rule.

Why 98% Is So Dangerous

The real problem with 98% is the constant negotiation.

Should I have one drink?
Just tonight?

Should we pivot?
Should we keep going?

Every decision drains energy.

100% eliminates the conversation.

No debate.
No bargaining.
No exceptions.

The rule becomes the system.

And systems beat motivation every time.

Lesson Learned:

If something matters enough, make the rule simple.

100% is easier than 98%.

3-2-1 Sprint

3 Ideas

1. Remove the negotiation.
If you’re debating every decision, your system is broken.

2. Use binary rules.
No sugar. No alcohol. No quitting. Clear rules free mental energy.

3. Design your environment.
Discipline isn’t about strength. It’s about removing temptation.

2 Quotes

“It’s easier to hold your principles 100 percent of the time than it is 98 percent of the time.”
— Clayton Christensen

“If something is important enough, you do it even if the odds are not in your favor.”
— Elon Musk

Contrarian Corner

Most people don’t fail because the goal is too hard.
They fail because they operate at 98%.

Last year I got tired of eating so much refined sugar.

All year I tried moderation.

“Just a little.”

It never worked.

So this year I made a rule:

365 days with ZERO refined sugar.

The first two weeks were hell.

But now it’s been about 2.5 months.

And surprisingly…

it already feels easy.

All thanks to the 100% rule.

Sometimes the hardest rules make life the simplest.

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In an old NFL interview, Peyton Manning said something that stuck with me:

“I may not be the best, but no one can out-prepare me.”

He knew he was not the most physically gifted quarterback in the NFL.

What Manning Actually Did

While other quarterbacks were natural athletes, Manning was something else entirely.

He watched more film than anyone. He memorized defensive schemes. He showed up to training camp already knowing the playbook cold, then spent camp learning the opponent’s playbook.

His preparation wasn’t a habit.

It was an obsession he turned into a system.

And that system won him two Super Bowls, five MVPs, and the respect of every defensive coordinator who ever had to prepare for him.

He wasn’t the fastest. Wasn’t the strongest arm.

But nobody walked into Sunday more ready.

The Gap Between Talent and Preparation

Here’s what Manning understood that most of us miss.

Talent may get you in the room, but preparation is what actually determines your long-term outcome.

We romanticize the gifted athlete. But the less sexy truth is that what looks like instinct is usually just rehearsal nobody saw.

Edison’s genius when inventing the light bulb → “I’ve just found 10,000 ways that won’t work.”

On The Running Track

Running taught me the same lesson.

The runners who plateau early are, ironically, often the most gifted. They rely on what came easily, and when the field catches up, they don’t know how to respond.

The ones who keep improving are boring. They track splits obsessively. They study their form. They do the drills nobody posts on Instagram.

They out-prepare, eventually outperform.

In Business, Same Game

The best founders I’ve met are the ones who’ve already practiced the sales pitch a million times before talking to the customer. They know every objection before the client raises it.

Preparation is the one advantage that’s always available.

Manning-level preparation means preparing until you can’t be surprised.

3–2–1 Sprint

3 Shifts to Make

1. Before Monday, find a Manning habit that you uniquely have; the one rep nobody sees but you.

2. Stop preparing to feel confident. Prepare to feel inevitable.

3. Acknowledge that the person you're competing with is preparing right now.

3 Quotes I like

• “I may not be the best, but no one can out-prepare me.” — Peyton Manning

• “Luck is what happens when preparation meets opportunity.” — Seneca

• “I have not failed, but found 1000 ways to not make a light bulb". — Edison

1 Question to Ask Yourself

Where are you secretly relying on talent to will do the work that preparation should?

Counterintuitive Corner

The one who looks effortless worked the hardest before you arrived.

End Note

Manning retired as one of the greatest ever. Not because he was born that way.

Because he decided that no one would out-prepare him, and then spent two decades proving it.

That’s a decision any of us can make.

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Last week, I climbed Volcán de Acatenango to witness the breathtaking eruptions of Volcán de Fuego — an active volcano standing over 3,800 meters. I did this with my whole family, including my three kids: ages nine, seven, and six.

Before embarking, most people told me the same things.

“Kids can’t do that. Only adults are able.”

“They’ll get altitude sickness. It’ll be a nightmare.”

“They’ll get bored. They’ll be miserable. You’re going to ruin the experience for them. ”

Everyone had a reason it wouldn’t work. Everyone was certain. And nearly everyone, it turned out, was completely wrong.

I had climbed with them on a few less demanding ascents, and based on those experiences, I assessed that they were more likely to make it than not. So I paid the deposit.

The Climb

Volcán de Fuego is not a casual hike. The ascent takes six hours with over 1,000 meters of vertical gain. The terrain shifts from dense jungle to loose volcanic rock and to open ridge.

We started early. The kids — a nine-year-old girl leading the charge, a seven-year-old boy in the middle, and his six-year-old brother at the back doing his own thing at his own pace. We set off up the trail without ceremony, without complaint, and without any apparent awareness that what they were doing was supposed to be beyond them.

I’ll be honest: inside my head, I was nervous. Not at all certain they would summit. As we climbed, I kept a quiet eye on their pace and mood, ready to make the call to turn back.

The first few hours were steady. Other adult groups passed us on the way up with polite smiles—the kind that said they admired our ambition even if they doubted the outcome.

Then something shifted.

Around the halfway point, the altitude began to wear people down. Pace slowed. Stops became more frequent. Conversations shortened. The mountain was collecting its toll — and that’s when we started passing people.

As we moved through groups, you could hear it:

“Don’t complain — look at those kids.”

Adults coming down after a night at camp would spot my kids and nudge each other. Adults we were overtaking would fall quiet as my six-year-old moved past them at a pace they could no longer match. Almost all of them laughed — not mockingly, but with genuine disbelief. One man shook his head and smiled at me. I replied with a face that said: I have no explanation for this either.

It wasn’t all smooth going. They struggled at times, like anyone else. But they recovered, forgot about it, and kept moving. That part, I noticed, was distinctly un-adult of them.

The Last Mile

The final stretch is a different kind of suffering. The trail flattens slightly before the last push, but by that point, most adults are running on empty. People who had been confident at the base were now shuffling. Nobody was talking. The mountain had stripped everyone down to something very basic: one foot, then the other.

That’s when my kids started running.

Not jogging. Running.

They had sensed the end was near, and I stopped holding back their urge to sprint to the finish. They bolted. Our mountain guide — a man with a rugged face from decades of alpine sun, who had climbed this volcano more times than he could count — looked at me and burst out laughing.

“The energy kids have,” he said, shaking his head. “It’s mind-blowing.”

He wasn’t wrong. But standing there watching them go, I had a different thought entirely.

It wasn’t their energy that was mind-blowing. It was their absence of doubt.

“It always seems impossible until it’s done.” — Nelson Mandela

What Kids Know That We’ve Forgotten

Adults carry invisible weight up a mountain. We know how hard it’s supposed to be. We’ve heard the warnings. We’ve calculated the distance, read the elevation, and prepared ourselves for failure before we’ve even begun. By the time we take the first step, we’re already negotiating — with ourselves, with the mountain, with our limits.

Children don’t do this. They haven’t yet learned that certain things are supposed to be out of reach. They haven’t accumulated the library of limitations that adults carry around like a second backpack. Ignorance is bliss.

My six-year-old didn’t know he was too young for this. My seven-year-old hadn’t logged enough experience to know he should be worried. My nine-year-old had no idea that the adults struggling behind her were thinking she wouldn’t make it. They just hiked — playfully, stubbornly, without a script.

The ceiling isn’t the volcano. The ceiling is the story we tell ourselves before we even get there.

The warnings people gave me were not based on my children’s actual capabilities. They were based on assumptions, their own fears, and limitations.

I’m not saying take your kids to unreasonable extremes. Assess the risks. Do the homework. But I will never stop asking myself: am I seeing my children’s limits clearly, or am I projecting my own? How much of what I believe about what they can’t do is real — and how much is a ceiling I accepted before they ever had the chance to test it?

Looking back, I’m still in awe. Not because my kids are superhumans, but because they didn’t just do it — they plowed past most of the adults on the mountain. I couldn’t have been more wrong to doubt them. They weren’t just capable. They were beyond anything I had expected.

Questions to Ask Yourself

• Where in your life have you accepted a limit that was handed to you, rather than one you discovered yourself?

• Is there something you’ve told yourself — or someone around you — is “too hard” or “not realistic”? What would actually happen if you tested that assumption?

• When was the last time you attempted something you weren’t sure you could do?

Burn the Playbook

Don’t ask or give out ‘easy.’

We think protecting people from hard experiences is kindness. It isn’t. Most of the time, it’s a limitation with better PR. The most damaging thing you can do to someone is deprive them of a difficult experience. Or even worse, it’s defining a ceiling they didn’t build and were never asked to question.

End Note

“Whether you think you can, or you think you can’t — you’re right.” — Henry Ford

Most of us aren’t held back by our own conclusions. We’re held back by conclusions we inherited. My kids didn’t summit that volcano because they were extraordinary. They summited because nobody had convinced them yet that they shouldn’t be able to.

Worth asking what you’ve accepted as impossible that you’ve simply never tried.

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Last week I wrote that talent is overrated.

An unexpected number of you replied.

Some agreed immediately. Some pushed back hard.

The Comfort of Calling Someone Talented

When someone builds a unicorn at 27, runs a 2:05 marathon, or sells like a machine, we reach for the same word:

Talent.

It sounds like admiration.

But often it’s self-defense.

If they’re gifted… then I’m not accountable. If they’re wired differently… then my mediocre results are justified. If they were born that way… then I’m off the hook.

Talent is the most elegant excuse we’ve ever created. And the cruelest part? It masquerades as humility.

The Story I Used to Tell Myself

When I was building Alameda — our first real company — I watched a competitor grow faster than us. Better product instincts and much better at raising capital. It felt like they were always 6 months ahead of us.

“He’s a natural,” I told myself.

It felt true. It also felt good. Because if the gap was innate, I didn’t have to close it.

Years later, we became friends, and I was surprised to find out about their crazy work ethic. Rewriting his pitch every Friday. Working tirelessly 80 to 100 hours per week. He wasn’t a natural at anything. He was a machine who’d disguised his reps as instinct.

The gap wasn’t genetic. It was behavioral.

And that was so much harder to accept.

The Part That Stings

Here’s what I didn’t want to see then, and what I think most people still don’t want to see now:

If discipline matters more than talent, the gap between you and where you want to be is mostly behavior.

Not destiny. Not wiring. Not circumstance.

Behavior.

Sit with that for a second.

Because when you accept it, something dies. The story you’ve told yourself — and maybe your family, your friends, your younger self — that you just weren’t built for this thing. That some people have it and some people don’t. That you’re being realistic, not afraid.

Behavior is controllable. And controllable means responsible.

It’s easier to applaud prodigies. It’s harder to ask yourself what 500 disciplined reps would actually look like — and then not do them anyway.

The Reframe

I’m not saying talent doesn’t exist. It does.

But talent without discipline is nothing. Average ability with obsession is lethal.

The founders who win aren’t usually the most gifted. They’re the ones who stay.

The runners who improve aren’t magical. They just out on Rainy Days.

3–2–1 Sprint

3 Micro Shifts

1. For one week, replace “talented” with “trained” when you describe someone — out loud, in meetings, in your own head. Notice what changes.

2. Identify one area where you’ve said “I’m not wired for that.” Write down what 10 disciplined, boring, specific reps would actually look like. Not a mindset shift. A rep.

3. Pick one metric that measures showing up, not outcomes. Track only that for 30 days. Protect it like it’s the result.

2 Quotes

• “We are what we repeatedly do.” — Aristotle

• “A big talent is just someone else’s tolerance for boredom.” — JC

1 Question

Where have you labeled something “not for me” when what you really meant was “I don’t want to commit to finding out”?

Contrarian Corner

Calling someone talented is often just a polite way of ignoring their work — and a quiet way of excusing your own.

End Note

I still catch myself doing it.

The talent excuse doesn’t go away once you name it, but it does get quieter. You learn to notice it faster and trust it less.

The aha moment is when you choose not to play the victim.

Thanks for reading.

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I used to think some runners were just built differently.

Effortless stride.
Natural speed.

Early on, I’d get dropped in workouts by guys who looked like they weren’t even trying.

They had talent.

For a while, that story puzzled me.

Until something interesting happened.

A few years later, most of them plateaued.

Some quit.

The ones who kept improving weren’t the flashy ones.

They were the boring ones.

The ones who tracked splits obsessively.
Adjusted cadence by 1–2%.
Reviewed form.
Sought feedback.
Did drills nobody posts on Instagram.

The Myth We Love

I absolutely recommend reading Talent Is Overrated by Geoff Colvin. He dismantles the myth that top performers are born special.

His core thesis is simple:

The best aren’t gifted.
They practice differently.

Not more reps. Better reps.

Deliberate practice.
Focused on weakness.
Uncomfortable.
With feedback.

Talent feels magical.

Deliberate practice is mechanical.

And mechanical wins.

Business Is the Same Game

We romanticize the “brilliant founder.”

The natural salesperson.
The visionary product mind.
The born leader.

But the companies that win aren’t led by superhumans.

They’re led by operators who:

Break down sales calls like game film.
Rewrite positioning weekly.
Study churn patterns obsessively.
Run postmortems without ego.

They treat performance as trainable.

That’s it.

It’s less sexy.

Talent gives you early validation. Deliberate practice gives you long-term dominance.

3–2–1 Sprint

3 Shifts to Make

• Focus: One weakness you’ll attack.

• Constraint: How you’ll make it uncomfortable.

• Feedback Loop: How you’ll measure real improvement.

• Non-Negotiable: What you’ll do even when motivation drops.

2 Quotes I like

• “It’s not that I’m so smart, it’s just that I stay with problems longer.” — Albert Einstein

• “Hard work beats talent when talent doesn’t work hard.” — Tim Notke

1 Question to Ask Yourself

Where am I secretly hoping talent will save me from disciplined practice?

Contrarian Corner

Calling someone “talented” is often just a polite way of ignoring their work.

Takeaway

For years, I thought I lacked something as a runner.

Turns out, I just needed better practice.

The comforting lie is: “Maybe I’m not built for this.”

The empowering truth is:
You haven’t trained hard and long enough.

Thanks for reading.

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I was training for the 2019 Boston Marathon.
Everything was going according to plan.

One morning, out of nowhere, I decided to do box jumps on a steel bench in the park to train my quads.
Bad idea.

Mid-air, my toes clipped the edge.
I went forward.
Both shins split open, leaving my shin bone exposed, and I went directly to the ER.

Just like that, my Boston plan evaporated.

The Moment After the Plan Dies

Lying there, I wasn’t thinking about pain.
I was thinking: Now what?

That’s the moment most people freeze — in running, in business, in life.

Because we don’t train for the plan breaking.
We train for the plan working.

What Actually Saved the Race

I couldn’t run for weeks.
So I trained everything else.

Pool running. Strength work. Mobility. Form.
Twice as hard.

To my surprise, when I came back, I wasn’t behind; I was better and ran my fastest marathon time ever.

The plan didn’t save me.
Adaptation did.

Business Is the Same Game

At its peak, BlackBerry controlled over 50% of the mobile phone market.

The plan worked — incredibly well — until it didn’t.

When the smartphone era arrived, BlackBerry clung to what had made them successful: keyboards, security, enterprise users. By the time they tried to adapt, the market had already moved on.

By 2016, their market share collapsed to 0.1%.

Most founders and managers respond to change by tightening their grip on the plan.
That’s how companies die.

The good ones do what runners do mid-race:
adjust pace, change strategy, and keep moving forward.

3–2–1 Sprint

3 Shifts to Make

• Measure progress by learning speed, not forecast accuracy.

• Optimize for recovery when things break, not for perfection when they don’t.

• Make adaptability the core value, not perfection.

2 Quotes

“Everyone has a plan until they get punched in the face.” — Mike Tyson

“It is not the strongest of the species that survives… but the one most responsive to change.” — Charles Darwin

1 Question to Ask Yourself

• Am I mentally and structurally ready to change paths if things don´t work out?

Contrarian Corner

Sticking to the plan is often just a more comfortable way to fail.

Takeaway

That injury hurt — physically and mentally.
But in hindsight, it removed the illusion that control was ever real.

What replaced it was better:
The realization that embracing change isn’t a weakness — it’s the actual winning muscle.

Thanks for reading.

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I’ve never met a serious marathon coach who didn’t hand over a detailed 9–12 week training plan on day one.

Mileage. Pace ranges. Long runs. Recovery days.
A blueprint of where to start, how to progress, and where this is supposed to end.

Later in my running career, when I started coaching both first-timers and sub-3-hour marathoners, one thing kept showing up: how uncomfortable runners felt until they had the 12-week plan in their hands.

Before the plan: anxiety.
After the plan: calm.

Nothing had changed physically.
But mentally, everything had.

That’s when I understood what the plan was really doing.

It wasn’t guaranteeing an outcome.
It was making starting feel real.

What a Marathon Plan Is Actually For

When you sign up for a marathon, the plan does a few important things:

• It forces commitment. Writing it down makes it real.

• It gives structure to your weeks.

• It creates a sense of progress before results exist.

Planning feels productive.
And that’s not wrong.

But planning is still not the work.

Business Works the Same Way

As entrepreneurs, most of us obsess over plans:

• Business plans

• Go-to-market plans

• Hiring plans

• Revenue forecasts

That’s not a flaw. It’s a feature.

In business, plans do what training plans do in running:

• They force clarity.

• Plan for the unforeseen.

• They create momentum before certainty exists.

The mistake is believing the plan defines outcomes.

It doesn’t.

Plans don’t eliminate uncertainty.
They just make uncertainty less paralyzing.

Takeaway

Have a plan so you can begin. Let go of it so you can continue.

3–2–1 Sprint

3 Micro Ideas

• Use plans to visualize direction. Don’t hope for it to guarantee results.

• Treat planning as preparation, not progress.

• If planning feels productive, ask what action it’s delaying.

2 Quotes that I like

• “Plans are nothing; planning is everything.” Dwight D. Eisenhower

• “I may not be the best, but no one can out-prepare me.” Payton Manning

Contrarian Corner

Overplanning isn’t discipline. It’s fear to face the unknown or the uncomfortable.

End Note

Every meaningful marathon cycle I’ve had started with a plan. None of them was made by it. The plan just helped me lace up when motivation wasn’t there. Business has been exactly the same.

Thank you for reading.

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Early in my career, I learned this lesson the hard way.

I started my first company, Alameda, with a friend from Business School.

As we began building the company, we were also recruiting for corporate jobs—just in case.

He received an offer from McKinsey, the world's top-ranked consulting firm.
I got one from Redfin, a shiny Silicon Valley unicorn.

Then, Alameda took off.

It stopped being a school project and became a real company.

So we agreed to go all in.

I dropped my offer.

McKinsey, however, told my co-founder something different—very astutely:

“You don’t need to reject the offer. Defer it for six months. If the project doesn’t work out, your seat is waiting.”

It sounded perfect.
A golden parachute.

The first three months were all growth.
Then, in month four, we hit a wall. Revenue stalled.

One morning, my co-founder walked into the office without his backpack and asked to talk.

“I don’t think I can continue.”

That was it.

I was left alone, trying to rescue what would later become the largest furniture and home décor marketplace in Latin America.

When things got hard, he didn’t face uncertainty.
He faced the seductive comfort of McKinsey.

And that’s when I learned:

If you have a Plan B, that is your Plan A.

Takeaway

Plan B doesn’t make you safer.
It makes quitting easier.

3-2-1 Sprint

3 Micro Ideas

1. If something worthwhile feels too safe, you’re probably hedging.

2. Remove optionality in public. Tell people what you’re doing so backing out costs reputation.

3. Write down your Plan B—and make choosing it painful.

2 Quotes

• “If you have a Plan B, that is your Plan A.” — Learned the hard way

• “Necessity is the mother of invention.” — Plato

1 Question
Where in your life is Plan B quietly running the show?

If you’ve ever debated whether having a Plan B is a good idea, forward this to that person.
And if you’re in it yourself—hit reply. I read everyone.

Share

Then I refreshed my inbox. Nothing impressive happened. A few subscribers trickled in, but no swarm of new readers—like anyone would secretly hope.

Just the quiet realization that now I actually have to do this again.
And again.
And again.

It feels familiar.

Like when I sign up for a big race.

Excitement is everywhere. I screenshot my registration email and share it with friends and family. Everyone congratulates me.

Then day two comes along.

No more congratulatory messages.
The euphoria vanishes.
Silence takes over.

Even worse, it turns into doubt.

I’ve felt this in startups as well—right after the excitement of “we’re doing this” fades and you’re left with questions like: What do we do now? or Why isn’t anyone buying our product?

There’s no feedback that things are working.

Starting is a moment.
Continuing is the real challenge.

In 2018, I was watching an interview on Instagram with Desiree Linden. She had just won the Boston Marathon—breaking a 33-year drought of American winners.

As she was being interviewed, the interviewer asked her:
“What’s your number one tip for runners out there?”

I was on the edge of my seat, pen and paper in hand, craving some secret insight—training methods, recovery dynamics, a race-day trick.

Her answer?

“Just show up.”

What?!

That was it?

No silver bullet? No hack to become a faster runner?

At the time, I was a novice runner looking for a miracle. I was disappointed—almost angry—at what felt like a useless piece of advice.

Many years later, after becoming a professional marathon runner, I realized how much wisdom that small phrase carried.

Just show up.

In marathon training, this is where most people drift. Not at the wall. Way before that.

They skip one run this week.
Then maybe another the next.
And eventually they don’t quit—they just quietly stop training.

Startups die the same way.

Not with a dramatic failure.
But with silence.

Ouch.

Here’s the uncomfortable truth I keep relearning:

The hardest part isn’t starting.
It’s showing up when nobody is watching.

No pitch-deck applause.
No race-day crowds.
No external signal that says, yes, this matters.

Just you… and the dull work.

Takeaway

If what you started already feels a little flat, a little lonely, a little pointless—congratulations.
You’re exactly where it starts to count.

3-2-1 Sprint

3 Micro Ideas

1. Decide the cadence once. Never renegotiate it.

2. Measure reps, not reactions.

3. When it feels boring, zoom out—boredom is a sign you’re early, not wrong.

2 Quotes that I like

“Most people stop not because it’s hard, but because it’s quiet.” — Anonymous

“Just show up.” — Desiree Linden

A Question to ask yourself

What did you start recently that now feels… awkwardly unexciting—and what would happen if you kept going anyway?

So, if you know someone in the quiet middle, forward this to them.
And if you’re in it yourself, hit reply. I read everyone.

Share

Every excuse was there:
Who cares?
Who am I to write about anything?
What if I sound pedantic?

Then I remembered that I always preach signing up for a marathon, even if you are not ready.

So instead of waiting to feel ready, I am deciding to start.

Screw it. Let’s go.

The Uncomfortable Truth

Most of us wait our whole lives for the perfect time to begin.

But that time doesn’t exist.

Starting is never logical. It’s emotional.
You’re either scared — or you’re lying.

That unease you feel? It’s not a warning sign. It’s the entry fee.

In 2015, I needed $200K to launch my second tech company, Alameda.

We had no product.
No customers.
Just conviction — and fear.

I asked my brother for $40K.

Secretly, I was hoping he’d say no.

He didn’t.

He wired the money the next day.

That was the point of no return. The ships were burned. There was no turning back.

And that’s when the real work began. Not because I suddenly believed more, but because escape was no longer an option.

The Lesson

You can’t think (or overthink) your way into momentum.

You have to commit.

In marathoning, it’s paying the entry fee.
In startups, it’s spending real money — or raising it from people who believe in you.

Waiting for confidence is a trap.

Confidence comes after action — through exposure to risk, uncertainty, and the unknown.

If you want to do, you have to start.

3 Micro Ideas

• Public commitment beats private motivation. If no one can see it, it’s optional.

• Pay something you’ll regret losing. Free plans don’t change behavior.

• Borrow pressure. Money from someone you respect sharpens commitment like nothing else.

If you have a Plan B, that’s your real Plan A.

Forget the MBA Spotlight

🧠 Founder Fail
I once asked my brother for $40K to launch a startup — secretly hoping he’d say no.

He said yes.

That yes cost me sleep for 18 months.
It also made me a founder.

End Note

I’ve seen the same pattern again and again.

The people who do extraordinary things never feel ready — they just start anyway.

My challenge to you: make your first move today.

Sign up.
Invest the money.
Call them.
Lace up.

Reflective Question

What’s the uncomfortable action you’ve been avoiding because you’re waiting to feel ready?

My Commitment

I’m publishing this newsletter every week for Q1 2026 — even if no one reads it.

If I miss a week, I owe an explanation in the next issue.

If you’re reading this, you’re now part of the deal, and you can hold me accountable.

Thanks for reading. Have a great week.

If you want the next one, subscribe. One email a week. Zero fluff. No MBA required.

Last year, I was having tea with a group of entrepreneurs and adventure seekers somewhere deep in the Sahara Desert. We were about to embark on a 250-kilometer ultramarathon across the dunes.

One of them mentioned a podcast he’d heard about a man who had done a “darkness experience.”

You are placed in a room buried inside the hills of Oregon - alone in absolute

darkness for four days with no light, no sound, no phones, no clocks, no stimulation of any kind.

The idea instantly grabbed me. Mysterious. Primitive. Raw.

I emailed Scott, the owner. The earliest opening was in 2027, three years away— it sounded safely far. I paid the deposit.

A few months later, out of nowhere and without much thought, I sent him another email:

“Any chance you’ve had cancellations? I’d love to come sooner.”

“You’re in luck,” he replied. “A cancellation just opened for next month. Do you want it?”

A cold shiver ran through my spine as I read those words.

One month? That’s too soon.

But I had already taken the step. I couldn’t back down.

“Amazing!” I emailed, pretending to sound excited.

The timing couldn’t have been worse. Our company had just acquired a competitor, and things were going through a rough patch. I was asked to step in as interim CEO—a rescue mission of sorts.

Overwhelmed with work and family commitments, I couldn’t prepare for the dark. I boarded the plane and put the audiobook Scott had recommended on at double speed.

As soon as the plane took off, I fell asleep, not to remember a single word.

Just as skipping marathon training, I’d soon pay the price for my lack of preparation.

Scott picked me up at a small airport in southern Oregon. He was barefoot, driving a dusty Toyota pickup.

We left the highway and climbed into the mountains. A herd of deer crossed in front of us. That’s when I realized I’d forgotten to tell my family I was about to lose cell coverage. Too late.

Scott kept driving up the Oregon hills. The scenery was beautiful, but my thoughts began to twist as I acknowledged how unreachable I was.

Eventually, we arrived. Scott parked and dropped me at the entrance of my “cave”—a small room built into the side of a hill. He invited me to walk in.

As soon as we crossed the doorway, the air shifted—from fresh mountain breeze to a still, confined atmosphere. A second chill ran through my neck.

Scott showed me the basics: how to use the tub, where the toilet paper was—the essentials. I noticed there was no mirror above the sink. Then he showed me how the light switches were protected by a plastic cover that had to be popped open to use.

“I didn’t know I’d be able to turn the light on if I wanted to,” I said.

He laughed. “Of course, this isn’t a prison. If you want to leave the dark, that’s your choice. The cover just keeps you from flipping it accidentally.”

He then walked me to the corner and pointed to an odd-looking object—something like a miniature reading lamp. He clicked it. A red light glowed.

“If at some point you feel the need to gently get out of the dark, this is your escape mechanism,” he said.

“Not me,” I thought. “I’d never cave.” My ego whispered.

Test Day

Scott explained that the first night was a kind of test run—to see what complete darkness felt like, to then come out sometime the next day.

“See you on the other side.“ He said, climbed into his pickup, and disappeared, leaving behind a cloud of dust.

“What? That’s it?” I thought. “What am I supposed to do now?”

The first thing I did was step back into the cave and shut the door. Completely alone, the third chill ran through my spine. Slowly, I approached the light switch. I stared at it for a long time. It felt like facing a nemesis. I lifted the plastic cover and, for the first time, tested complete darkness.

The moment I flipped the switch, a primal fear flooded every cell of my body. Instinct won—I turned the light back on.

In ordinary darkness, your eyes begin to adjust. Not here. This was black beyond adaptation—where even your own hands vanish inches from your face to never return.

Years earlier, on another adventure sailing across the North Atlantic, I remember thinking,

What are you doing? Why are you here?

For the first time since then, that question resurfaced.

It felt strange to be inside, so I walked outside. The air, the trees, the sounds—everything was easier than what awaited behind that door. I spent the afternoon outside, sitting in a wooden Adirondack chair overlooking the hills, eating warm vegetable soup from a camping can that Scott had left me.

My last meal in the light.

As the sun began to set, anxiety crept in. I glanced behind me at the door buried in the hillside. I took a deep breath, stood up, and walked toward it.

Scott’s words echoed: Try to be in the darkness, and see how you feel.

I’m a good student, so I followed the instructions. I walked in and shut the door behind me. I unpacked slowly, placing things logically where I could find them in the dark. I lit a candle and filled the tub for a warm bath.

Lying in the water, I watched the flickering flame. One thought filled my mind: That candle won’t burn forever.

There was no turning back.

When I got out, I stood in front of the candle, ready to blow it out—but I hesitated. I walked back to my bag, arranging things I didn’t need to arrange. I was procrastinating.

Finally, I faced the candle again and blew it out. In an instant, darkness swallowed me whole.

What are you doing? Why are you here?

I found the bed, and before my mind could spiral too far, I fell into a deep sleep.

At some point, I started dreaming—shapes, whispers, sounds. But then, I woke up abruptly. The sounds weren’t dreams; they were real. Someone was trying to force the door handle open. My eyes shot open into total darkness.

My body froze. Complete silence followed. My senses screamed to see, but there was nothing. Just black.

The sound came again—metal against metal, deliberate and slow. I was paralyzed. Freeze, fight, or flight? My system chose freeze.

I tried to yell, but my throat sealed shut. I lay frozen—like a deer sensing the faintest twitch of its hunter.

Finally, with effort, I forced out a few words.

“Scott? Is that you?”

Silence.

“Who’s there!?” I yelled, louder this time.

Then came the worst feeling of all: I sense someone is already inside, but I can’t see them.

That thought pulled me into another dimension of fear. Freeze turned into a cautious fight. Heart racing, I slowly pulled my legs off the bed, stretched my hands out in front of me, and walked forward, ready for whatever waited.

I remembered counting four steps from the bed to the door.

One. Two. Three. BAM!

On the fourth, my palms met the closed wooden door.

I shuffled my hand over the knob—still locked. Relief poured through me like a wave. No one was inside. No one was behind me.

I took a long breath, turned, and walked back. One. Two. Three. Four.

Back in bed, my heart began to slow. Then—click, clack! The sound again.

I jumped up, hurried to the door, but the noise had stopped. Fear evolved into frustration. What’s going on?

Then I heard it again—from above this time, softer, more organic.

Scott’s voice echoed in my memory: “Remember, the cave is built into the ground, so animals may walk over it.”

I exhaled, still uneasy but calmer. I grabbed my aluminum water bottle and set it by the door. If anyone opened it, I might not see them—but I’d hear the clatter of metal on stone.

Lying back on the bed, that bottle became my new sense of security.

And then, as I stared into the abyss, I realized something: It had never been a door handle, but an undeniably convincing story constructed by the mind.

That’s how fear works—it starts with an outside stimulus, but the real noise is the one your mind makes inside.

Fool me once.

I reached for my earplugs, slipped them in, and drifted into one of the deepest sleeps of my life.

I woke late the next morning, drained from the night before. All I wanted in that moment was to flick the light back on—but I resisted an early exit.

“Not on test day,” I told myself.

I moved through the dark, stretching, feeling for balance. Breakfast became an odyssey of its own.

Simple things became absurd puzzles in complete darkness. I misplaced and lost my towel for two days. When I tried to journal, I had to feel the tiny indentations my pen left on the paper, tracing them with my fingertips to avoid writing over my own words. Even adding the Tabasco I had brought to a meal was a gamble—sometimes nothing, sometimes a firestorm.

In a small compartment that connected to the outside, Scott had left ten Tupperware containers for the day’s meals.

The first challenge was to figure out what was in each one. I shook each one beside my ear, hoping the sound would tell me something. One rattled—nuts, maybe. The others, silence. I opened them one by one, touching, smelling, guessing.

Boiled eggs, I discovered—no doubt. I smiled at the small victory, then frowned as I hated boiled eggs.

I kept going and shaking, sniffing, exploring until I touched something that felt like a human finger. My body jolted; I dropped it instantly.

My mind again.

I reached back in, slower this time, and pulled out the “finger.” A chopped carrot.

I chuckled in the dark. Breakfast: boiled eggs and apples feel like a triumph.

By around one in the afternoon, I decided I’d done enough for the test day. I opened the door and let light flood the room—eighteen hours in darkness.

As I stepped outside, I couldn’t help thinking: If this was just the test, what’s the real thing going to be like?

Day One

Later, Scott drove me down to a small cabin deep in the forest—a lonely hut with a piano and a MacBook Pro on a wooden table. I had a Zoom call scheduled with a guide who would talk me through what to expect.

I told her about my horror-movie night. She smiled.

“Well, you had quite the adventurous first night,” she said.

“Doesn’t everyone?” I asked.

“Not really. Yours was pretty extreme with too much noise. Why didn’t you just turn the light on?”

I didn’t answer. She´s right. It was only the test night, why didn’t I?

Then she explained something that changed everything.

“Imagine you and I are walking through a dense forest in the middle of the day,” she said. “We hear a branch crack behind us. We turn and see it’s just a squirrel. We keep walking. If someone asked us later, we probably wouldn’t even remember the sound—it registered, but only subconsciously.”

“Now picture the same thing at night—pitch dark. No flashlight. We hear the same crack. We turn but see nothing. Our brain goes wild—cougar, bear, murderer. We crave visual confirmation to calm the alarm, but when sight gives us nothing, the imagination fills the void. That’s what happened to you in the cave. Your mind needed to protect you, so it created that horror story.”

I nodded slowly. So that’s what happened.

It struck me how often the same thing happens in entrepreneurship—when the path ahead isn’t clear, we fill the void with fear.

“Oh man,” I said. “I should’ve prepared.”

But that lesson—the medicine of the first night—was precisely what the patient needed for what was coming.

Before going fully offline for the next four days, I used Scott’s Starlink connection to call my family. They asked about the test night. “It was actually pretty good,” I lied.

I hiked back toward the cave, anxiety rising with every step.

As dusk fell, it was time to return to the unknown for the start of day 1.

Inside, I set up my bed and clothes, lit a candle, and turned off the lights. Sitting cross-legged on the floor, I stared at the flickering flame. I remembered my kids asking, “What are you most afraid of, Daddy?”

“I’m not sure,” I’d said. “But blowing out the candle seems pretty chilling.”

Now the moment had come. The feeling was identical to the seconds before a big marathon race—a collision of nerves, excitement, and trapped energy.

I looked at the candle. “Here we go,” I whispered, and blew softly. The flame danced, refused. I took a deeper breath and blew harder.

It went out.

For a few seconds, I could still see the red ember of the burning wick, but then even that vanished. Darkness—complete and alive—wrapped around me. It felt like the starting gun of an ultramarathon, except this time there was no release, no forward motion, just a plunge into a dark void.

I brushed my teeth, checked that the door was locked, placed the aluminum bottle in front of it, and crawled into bed.

I guessed it was around 8 p.m.

When I woke again, I thought it was 10 a.m. I felt restless, like I should get up and do something. Then I remembered what the guide had said:

“You might sleep a lot on your first day. Let your body rest—the following days won´t be as sleep-generous.”

So I did. I rolled over and surrendered. I think I slept eighteen hours in total, collecting twenty years of lost sleep.

Day One: hibernation.

Day Two

The next morning, I woke earlier—maybe seven? Scott had said he’d check on me in the morning, but Scott never arrived.

Perhaps I’d misheard him.

Around two p.m., he finally arrived.

“What time is it?” I asked.

“Eight a.m.,” he replied from outside the door.

Wait—what? That meant I’d woken at two a.m.

He asked where I was in the room. “On the bed,” I said, suddenly realizing something the guide had mentioned: Some people never leave their beds; it becomes their safe zone.

As if it weren’t embarrassing enough to admit I was still curled in the bed, he asks whether my eyes are open or closed. Only then do I realize — I’m on the bed, eyes shut. Fear had been sitting with me all morning, and I hadn’t even noticed.

Scott led me through an exercise.

“With your eyes closed, touch your fingertips together. Focus on that feeling. Now, without losing focus on your fingers, slowly open your eyes.”

I did. The fear was still there, but I felt in control.

After lunch, I sat on the floor. On the west corner of the room lay a meditation mat, but for some reason, I felt repelled by that corner. It felt… wrong. Creepy.

I heard the guide´s voice again: If there’s an area in the cave that scares you, go there.

Against every cell in my body’s will, I walked over and sat down. My stomach twisted. I tried to breathe.

Then something strange began to happen.

In the dark, with nothing to distract me, my mind started to play a movie from childhood. I was nine, playing ice hockey. My dad watched from the stands. I was part of the first line of my team—the strong line. I was a pretty good player.

I skated around the opponent’s goal. I could hear the scrape of blades on ice, as well as the tapping of sticks. A teammate passed me the puck. I moved forward, saw the opening, and… froze. I didn’t shoot.

The scene looped. Over and over, my nine-year-old self choking.

And then something unexpected happened.

The scene split. There were now two of me—the boy and the man.

I stepped toward my younger self. “Why don’t you shoot?” I asked softly.

“Are you afraid you’ll miss? Are you afraid of your coach or your dad?”

The boy looked down at his skates.

Silence.

Then, quietly: “I’m just afraid.”

My heart broke for him—so small, so alone.

I sat beside him, arm around his shoulders. The words that came out of me surprised me.

I’d grown up in a family of hypercompetitors. Typically, I would have said something like, Winners shoot, my boy.

But instead, I heard myself say,

“It’s ok to be afraid.”

The sentence hung in the air—simple, weightless, true.

I got close to his ear and whispered, “Let me tell you a secret. Close your eyes and press your fingertips together. Feel the texture, the warmth, the pressure. Stay focused on that feeling. Now, slowly open your eyes, but keep your attention on your fingertips.”

He did. And as he did, I saw relief spread across his small face.

For a moment, I forgot where I was.

Then I snapped back into the dark room.

“Wow,” I whispered out loud.

That afternoon, I told Scott what had happened.

“Have you seen Interstellar?” I asked.

“I have,” he responded without losing a beat, as if he knew where this was going.

I explained how I’d just lived my own Interstellar moment—the way the father in the movie speaks to his daughter across time. I felt like I’d reached back to my younger self to give him something priceless.

As I spoke, tears ran down my cheeks. It startled me; I had never cried in my adult life.

Scott listened quietly, then said, “You just reminded me of a poem.”

He drew a breath and recited, voice deep and clear:

We shall not cease from exploration

And the end of all our exploring

Will be to arrive where we started

And know the place for the first time.

When he finished, I said softly, “T. S. Eliot,” with what was surely a face of stupefaction.

Inside, I thought, This can’t be.

I’m not exactly a poetry person; Eliot might be the only poet I know by name. I’d come across his words only weeks before in a random post that hit me hard enough to Google him.

Coincidence or not, it left me still as a fox, sitting there in the dark, I thought, Maybe this is why I came.

When Scott left, unease and fear crept back. I became frustrated. I’d seen more than I’d asked for, but all of a sudden I was back at it. “Darkness is more like a rollercoaster than a steady line.” The guide had said. One moment you’re a serene Samurai, the next, a terrified child.

I sat on the low desk and scribbled in my notebook:

Two more days. #embracethestruggle.

Day Three

An unusual calm settled in. I spent most of the day lying on the floor, staring into nothing. Time dissolved.

“Nothing happened today,” I wrote later. “I feel like a still lake.”

I always hurried away from the small desk after jotting notes; that corner felt uneasy, too. But that night I forced myself to stay. Resting my forehead on my folded arm, I started to hum—ommm… ommm…— that meditation sound you see performed by monks. I didn’t mean to, I just started doing it. The vibration pulled me deeper and deeper until I slipped into the most profound meditation I’d ever experienced.

Once again, a new insight arose where fear was waiting. I was starting to see a pattern.

Day Four

The next morning, eager to return to that state of mind, I went straight to the meditation mat—the same one that had once felt haunted. It no longer did. I sat down and began chanting aloud again. Soon, I was outside myself, watching the person who was meditating. At times, I was in the cave; at others, somewhere high in the Himalayas. My mind was still, like glass water.

A knock brought me back.

“Juanca,” Scott called. “It’s time. Are you ready to walk into the light?”

A strange conflict rose in me. Part of me wanted out—desperately. Another part wanted to stay, to slip back into that other world.

I stood, found the eye mask, and tightened the Velcro behind my head.

“Let me know when you’re ready,” he said.

“Ready.”

I removed the lock and pulled the door open—BANG! - the noise from the aluminum bottle tipping over.

I’d forgotten the aluminum bottle I’d left there on day one. I couldn’t help but laugh at my paranoid earlier self.

Barefoot, I stepped outside.

A rush of cool air hit my face—pure, wild, divine. I’d been craving light, but I hadn’t realized how heavenly a breeze could feel after four days underground.

My foot landed on a large flat stone. It was cold and smooth, and the texture under my skin felt alive.

Scott took my arm and guided me slowly toward the same chair where I’d eaten my last meal in the light. Each step was its own adventure—the crunch of gravel, the brush of wind, the sound of forest life waking up around me.

A flock of geese passed overhead. I stopped, listening.

When we reached the chair, Scott helped me find the armrests. “Whenever you’re ready,” he said.

I sat still for a long time, just listening—the birds, the rustle of leaves, the deep quiet between sounds.

Finally, I reached back and undid the Velcro. I lifted the mask but kept my eyes closed. My eyelids glowed orange; the first color I’d seen in days.

Slowly, I opened them. The flood of light felt overwhelming, like drinking from a fire hose. My eyes adjusted by tiny increments until I could focus on the mountains in front of me.

Then, unexpectedly, disappointment hit. My chest tightened; my breath turned shallow.

Scott must have noticed. “What’s wrong?” he asked.

I hesitated. I didn’t want to sound shallow or ungrateful.

“For some reason, I feel… disappointed,” I said finally.

He stayed silent.

“I thought this would feel like a rebirth,” I continued. “I tried not to watch too many videos about dark retreats, but the few I saw—people were sobbing when they came out, saying they were seeing God. I don’t feel that. I feel like the same guy. Like I was sitting here eating vegetable soup from a camping can a few hours ago.”

Scott smiled—not pity, but understanding.

“You had a less common journey,” he said. “For reasons I don’t fully understand, some people begin to feel at ease in the dark. The more serene you become, the smaller the contrast when you take the facemask off.”

“I was definitely not ‘at ease’ but… yes, somehow it all felt like it happened in an instant.” I thought.

That Friday afternoon, as we drove out, Scott stopped by another cave to deliver food to someone still inside. He took a long time. When he returned, I asked, “Everything ok with my neighbor?”

He nodded. “Yeah. He was here last year, too, and has come back to continue the work.”

“What? People come back?”

I laughed. “What a lunatic.”

But a few weeks later, back in the noise of regular life, I understood why people go back to the dark—the silence, the solitude, the no-hurry. It feels nourishing to disappear into the mountains - you feel like Musashi.

Return

When friends asked if I’d recommend it, my answer was always the same:

A hard no—unless you really feel called. If you do, follow that instinct.

When they asked what it was like, I’d pause and say:

“It’s part nightmare, part enlightenment.”

In the dark, I didn’t beat fear. I just stopped running from it.

I sat with it. I stared into it. It stared back.

And after a while, I realized fear wasn’t trying to stop me—it was trying to show me something.

Coming out, I expected to cry and feel reborn. I didn’t. I was the same guy in the same chair overlooking the same hill—but something had shifted.”

That’s what Eliot meant. You go far, you struggle, you face the dark… and somehow you come back to where you started—and see it for the first time.

I saw something in the dark that cannot be unseen.

I’ll tell you a little secret.

September, 18th 2025

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