Leadership Lessons from 29029 Stratton: Overview
Every summer, my sons Jake, Mack, and I take on an endurance challenge together; our annual 29029 event. For those who haven’t heard of it, you get 36 hours to climb the vertical equivalent of Mount Everest (29029 feet) by hiking up a mountain again and again (and again). You sleep, eat, and recover within that same 36 hours.
This year, we decided to do this event at Stratton Mountain in Vermont where you have to climb 17 laps of 1750’ to reach the required 29029’. The weather was mostly okay, a mix of cool, foggy, and occasionally rainy. The terrain was steep, the hours were long, and as always, there were parts that just plain sucked.
Parts of 29029 just suck; there’s no better word for it. The steep sections, the cold rain, the fatigue that creeps in around climb six or seven. But the truth is, how much it sucks depends on how much you trained. The less you trained, the longer it lasts. The more you prepared, the quicker you move through it. It’s not unlike other endurance events, or leadership, for that matter. Preparation doesn’t always or totally eliminate the discomfort; it just reduces its intensity and duration.
For us, 29029 is more than an endurance event. It’s an opportunity to reset and reconnect. The 36 hours that we spend together is simple and priceless; we climb, eat, rest, repeat. Each lap, we name something we’re grateful for, no repeats. And during those quiet conversations, the laughter, and the late-night headlamp hikes, I’m reminded what real leadership looks like.
Each event reminds me of something different; at the end of Stratton, here are the five things that stood out most:
Purpose – doing something you’re proud of and choosing how you’ll remember it.
Grit – showing up and staying with it when its uncomfortable.
Presence – the quiet strength of encouragement and consistency.
Service – leading by helping others succeed.
Community – celebrating progress and belonging as much as performance.
Each of these lessons showed up on the mountain, but they apply even more so in leadership.
This week, I’ll share one lesson each day, not as a formula, but as a reminder that leadership, like climbing, isn’t about reaching the top. It’s about how we choose to climb together.