#145: Fall. Get up. Repeat.
What snowboarding taught me about ego and growth.
👋 Hey, Leo here. The Antifragile Leader is where I explore how leaders think, decide, and build in uncertain environments shaped by technology and change.
Each edition is a reflection, a principle, or a field note from the work itself.
Hey Friends,
Welcome to the 145th edition of The Antifragile Leader.
A reminder that tomorrow, Bülent Duagi and I are kicking off a series of AI x Business, in which we invite senior leaders from organizations that successfully deployed AI in their businesses.
Make sure you register here.
Initially, we were aiming for 30 spots, but because of the high demand, we let this one go for unlimited.
This is a shorter edition, and it’s also a couple of days late, but you will have to excuse me.
I just came back from a skiing vacation in Italy.
And while it was a lot of fun (as you can see in the photos below), it also hurt.
Especially my ego.
I first picked up snowboarding three years ago, in Bansko.
It was very hard, so until this year I didn’t practice anymore.
Did a couple of lessons one month ago and went to Italy with some friends who are pros.
And let me tell you, no amount of CrossFit, marathon training, or Hyrox competitions prepared me for the specific humiliation of a bunny slope.
My legs were on fire. My knees and my behind were bruised.
My ego took hits that training data couldn’t even capture.
At one point, a kid, probably eight years old, cut past me with the kind of casual confidence I have only in PowerPoint presentations.
But here is the thing. I kept getting up.
And with each day, I kept falling less.
I kept going longer. And faster.
After five days, I can’t say I mastered the sport.
But I can say I become a lot more confident.
And the experience had me thinking a lot about what it actually means to be antifragile, not in theory, not in a Substack post, but in practice.
The myth of “staying in your lane” is slowly killing your growth.
There is a certain kind of professional advice that sounds wise but is actually just comfortable.
“Double down on your strengths.”
“Focus on what you’re already good at.”
“Master one thing.”
And yes, depth matters. Specialization matters.
But if you never step outside of the domain where you are already competent, you are not building mastery.
Nassim Taleb writes that “wind extinguishes a candle and energizes a fire.”
Stress and discomfort are not the problem. The problem is being a candle and pretending you’re a fire.
Learning something new from absolute zero, where you have no reputation to protect, no expertise to fall back on, and no shortcuts available, is one of the most clarifying experiences you can put yourself through.
The Beginner’s Brain is a Leadership Asset
When you are a beginner, you cannot fake it. The slope does not care about your title. The board does not care about your LinkedIn profile.
You are immediately, uncomfortably accountable to reality.
That’s rare.
Most of us operate in environments where we can mask gaps or rely on patterns we’ve already built. Deliberately putting yourself in a situation where none of that works resets something important in you.
Marcus Aurelius wrote,
“The impediment to action advances action. What stands in the way becomes the way.”
The falls are the lesson. The bruises are the feedback loop.
The frustration is the signal that your brain is actually trying to rewire itself.
Some people see it as failure. I call it adaptation.
The Real Reason Most People Stop Learning New Things
It’s not time. It’s not access.
It’s ego protection.
There is a cost to looking incompetent, especially when you have spent years building credibility in something.
Choosing to be a beginner again feels like going backwards. Like you’re giving something up.
But what you are actually giving up is fragility.
The leader who only operates in familiar territory gets shocked by the unfamiliar. The person who regularly puts themselves in new, uncomfortable environments builds a different kind of nervous system.
They know what it feels like to fail and recover. They know that discomfort is temporary and that frustration usually precedes a breakthrough.
They have skin in the game in the most literal sense.
The Takeaway
By the end of the trip, I was not good. But I was less bad.
And the gap between “completely hopeless” and “somewhat functional” happened entirely through repetition, bruises, and choosing not to quit.
That is exactly how growth works in any domain.
Not through a framework. Not through a course.
Through contact with reality, feedback, and showing up again after the fall.
Here is what I’d want you to take from this.
Pick something you’ve been putting off because you’d be a beginner at it.
A new sport.
A musical instrument.
A new skill that has nothing to do with your current job.
Something where failing is visible and the learning curve is steep.
But don’t do it because it will make you more productive.
Do it because it will remind you that you are capable of growth, and that discomfort is not the same as danger.
The antifragile leader is the one who has fallen enough times to stop being afraid of it.
What is one thing you’ve been waiting until you felt “ready” to start?
Recommendations:
One of the best essays I read lately, on how to adapt to what’s coming. (Especially since the advice included “fostering an anti-fragile identity”)
If you have 4 hours, instead of watching 2 movies on Netflix, I would watch this:
And of course, you need to read the article that caused a scare on the stock exchange:
Thank you for reading.
If this resonated, forward it to someone who might benefit from it.
Stay antifragile.
Leo
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