Standing at the lip of Tuckerman's headwall, you don't think about the board meeting. You think about the line. That kind of clarity is what executives need more of.
Tuckerman Ravine is a glacial cirque on the southeast face of Mount Washington, the highest peak in the Northeast. Every spring, when the snowpack has built to depth and the headwall opens, skiers hike up from Pinkham Notch — 2.4 miles and 2,200 vertical feet with skis on their backs — and launch themselves down a 55-degree pitch above a 40-foot cliff band.
I won the Tuckerman Inferno. That race — one of the oldest ski races in the United States — doesn't care about your title, your fund, your exit multiple, or your corner office. It cares about one thing: whether you can stand at the top of something terrifying and go.
That experience shaped how I think about risk more than anything I've read in a business book.
The Difference Between Fear and Danger
Most people conflate fear with danger. They feel fear and conclude that the thing in front of them is dangerous. Sometimes that's correct. But often — especially for people who have been successful in controlled, predictable environments — fear is just the signal that something is unfamiliar and the outcome is uncertain.
At the top of Tuckerman's headwall, there is real danger. The consequences of a mistake are serious. But the racers who win aren't the ones who feel no fear — they're the ones who have learned to read fear accurately. To distinguish between "this is genuinely dangerous and I should stop" and "this is hard and unfamiliar and I need to commit."
The best business decisions I've ever made felt exactly like standing at the top of Tuckerman's. The stakes were real. The outcome was uncertain. And the only way through was full commitment.
Calculated Risk Is a Trainable Skill
Here's what most people don't understand about expert skiers, climbers, adventure racers, or any high-consequence athlete: they are not reckless. They are the opposite of reckless. They have developed extraordinarily refined risk assessment — the ability to read conditions, evaluate their own capability honestly, and make go/no-go decisions with speed and accuracy.
That skill doesn't develop in the office. It develops in environments where the feedback is immediate and the consequences are real. The mountain tells you immediately when you've miscalculated. The board meeting tells you three quarters later, if you're lucky.
Leaders who have athletic backgrounds — particularly in high-consequence sports — are better calibrated risk takers. Not because they're braver, but because they've trained their judgment in conditions where bad judgment hurts.
Full Commitment as Strategy
There's a principle in skiing that applies directly to leadership: half-committed turns are more dangerous than fully committed turns. When you hesitate mid-line on a steep pitch, you lose your edge. You fall. The commitment itself is what creates the stability.
I've watched this play out in executive decisions more times than I can count. The leader who half-commits to a strategy, hedging constantly, signaling uncertainty to their team — they fail more often than the leader who makes a call, commits fully, and adjusts from a position of momentum. You can always change direction. You can't recover from paralysis.
The Mountain as Board Room
Every spring I go back to Tuckerman. Not to race anymore — though I still might — but because the mountain reminds me of things the office cannot. That my body is capable. That real risk is clarifying, not paralyzing. That the best decisions get made when you're fully present, fully committed, and not overthinking.
If you've never stood at the top of something that scared you and gone anyway — find that experience. It doesn't have to be a 55-degree ski slope. It can be a ridge line, a climb, an open water swim, an adventure race. Find the thing that requires you to be completely present and fully committed.
Then bring that back to the office. Your decisions will be better. Your team will feel it. And you'll stop confusing discomfort with danger.