The Poker Face That Won Gold and Nearly Destroyed My Business Career

For the better part of fifteen years I trained myself to be unreadable. No flinching, no hesitation visible on my face, no tells of any kind. In short track speed skating, your competitors are right next to you -- sometimes shoulder to shoulder at 35 mph on a sheet of ice the size of a bball court -- and they are studying every micro-expression for any hint of doubt or fatigue or fear.

Show nothing, give them nothing, be a wall.

This wasn't vague mental strategy. It was deliberate practice, refined over thousands of races until it became automatic. I could be in searing pain from lactic acid buildup, afraid of the contact about to happen in the next turn, and my face would show nothing. Competitors couldn't tell if I was coasting or about to attack, and that uncertainty was a real weapon.

It helped win eight Olympic medals.

Then I retired & tried to build a business career and that same skill nearly wrecked everything.

My first real meeting as a retired athlete trying to break into business -- I remember sitting across from three partners at an investment firm in LA and realizing I had no idea how to behave. I'd prepared obsessively (that part carried over fine) but the social mechanics of the room were foreign.

In skating, preparation meant knowing every competitor's tendencies, their weaknesses. Information was leverage and you kept it close. In business, information was supposed to flow -- you were supposed to share what you knew & what you didn't know & build something together.

So I sat there projecting the same calm, unreadable confidence that had won gold medals, and the partners read it as disinterest or arrogance or both. Unlike on the ice where ambiguity worked in my favor, in a conference room it was poison.

Meeting went nowhere.

But the poker face was only the surface issue. The deeper problem was what was happening behind it.

I didn't know anything about finance, about deal structure, about real estate, about the thousand details the people in those rooms had spent decades building expertise around. And the terror of being exposed as someone who didn't belong -- a guy who went in circles on ice for a living now pretending to understand cap tables -- was so intense I doubled down on the only protection I knew.

Show nothing, give them nothing.

I studied their industries w/ the same obsessiveness I'd brought to skating. Hours reading about markets & valuations & portfolio theory, trying to catch up to a lifetime of experience in a few months. Probably worked harder at understanding business than I'd worked at anything on the ice, which is saying something.

But the studying wasn't what changed things.

When did the mask come off?

What moved the needle -- and I remember the specific conversation even though I can't tell you exactly when it happened -- was the first time I dropped the mask in a room full of people I was trying to impress.

Someone asked me a question about a market I didn't understand & instead of deflecting or giving a polished non-answer (the athlete move, the politician move, the move I'd perfected over two decades) I just said the truth. "I don't know enough about that yet. But I promise you I'm going to learn it faster than anyone you've worked with."

Energy in the room shifted immediately. Not the way I'd feared -- people pulling back, losing respect, mentally crossing me off the list. The opposite. They leaned in, started explaining things w/ more patience, opened up about their own gaps & uncertainties. Conversation went from performance to partnership in about thirty seconds.

And I realized, standing there feeling exposed, that the armor I'd spent fifteen years building was suffocating me in every room that wasn't a skating oval.

The pattern is almost universal. Not the skating-to-business transition specifically, but the broader dynamic -- something that made you exceptional in one context becoming the exact thing that holds you back in the next one.

I've sat across from executives who built careers on being the smartest person in the room, and now lead teams that won't speak up bc the boss always has the answer. Founders who survived startup chaos by controlling every decision, and now their companies can't scale bc nothing moves without approval.

The skill isn't the problem. The skill is real & earned. The problem is we keep deploying it automatically in contexts where it no longer fits, wired so deep we don't notice we're doing it.

Showing nothing on the ice meant power. Showing nothing across a boardroom table meant disconnection.

I want to be honest about where I am w/ this bc I'm not going to pretend I've got it figured out. The poker face still shows up -- in high-pressure conversations, in moments where I feel out of my depth, old wiring kicks in & I go blank. My face smooths out, voice goes neutral, and the people across from me can't tell what I'm thinking.

Difference now is I usually catch it. And I've gotten better at the small corrections -- naming what I'm feeling instead of hiding it, asking a question instead of projecting certainty, admitting when I'm lost instead of pretending I'm tracking.

Fifteen years of deliberate practice in one direction is a lot of neural real estate to rewire.

But what I keep coming back to: the thing that got you here is not always the thing that gets you there. And the hardest version of that realization is when the thing that got you here was great -- it wasn't a bad habit you need to break, it was your superpower. And you have to learn, somehow, to set down the weapon that won your biggest battles bc the next arena doesn't have enemies, it has partners.

That's harder than any race I ever skated. But I'm working on it.

The question I ask myself regularly is simple: what's the thing you're best at that might be costing you the most right now?

Not your weakness. Your strength. The thing you'd never think to question bc it's always worked.

People don't trust perfect. They trust real. And "real" sometimes means letting them see the parts you spent your whole career learning to hide.

--AAO

Subscribe to Hard Pivot