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 builds 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 drop into a 55-degree pitch above a 40-foot cliff band.
I won the Tuckerman Inferno, a pentathlon that ends on that headwall. Five legs: an 8-mile run, a 6-mile kayak, a 16-mile bike up to Pinkham Notch, then you grab your skis and race to the top of the ravine, and finish with a ski race back down it. The race doesn't care about your title, your fund, your exit multiple, or your corner office. It cares about one thing: can you stand at the top of something terrifying, hours deep into a race, and go.
That race shaped how I think about risk more than anything I've read in a business book.
The Difference Between Fear and Danger
Most people confuse fear with danger. They feel fear and decide the thing in front of them is dangerous. Sometimes they're right. But often, especially for people who've succeeded 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, the danger is real. A mistake has serious consequences. But the racers who win aren't the ones who feel no fear. They're the ones who learned to read fear accurately. To tell the difference between "this is 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
Most people don't get this about expert skiers, climbers, and adventure racers: they are not reckless. They're the opposite. They've built extremely refined risk assessment. They read conditions, evaluate their own ability honestly, and make go/no-go calls fast and accurately.
That skill doesn't develop in the office. It develops where the feedback is immediate and the consequences are real. The mountain tells you right away when you've miscalculated. The board meeting tells you three quarters later, if you're lucky.
Leaders with athletic backgrounds, especially in high-consequence sports, are better calibrated risk takers. Not because they're braver. Because they trained their judgment in places where bad judgment hurts.
Full Commitment as Strategy
There's a rule in skiing that applies directly to leadership: half-committed turns are more dangerous than fully committed ones. Hesitate mid-line on a steep pitch and you lose your edge. You fall. The commitment 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 doubt to the team, fails more often than the leader who makes a call, commits, and adjusts with 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. Because the mountain reminds me of things the office can't. 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. 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.