Leadership Lessons from 29029 Stratton: Pride as a Compass
Before each 29029, we ask ourselves, and each other, often, the same question: How do I want to remember this?
In other words, will we look back on this event with pride or with regret?
That question has become a compass for us, both on the mountain and in leadership. I wrote about it a while back in Will This Make You Proud?. When we pause long enough to ask what will make us proud six months from now, we usually find clarity about what matters today.
For my sons, Jake and Mack, and me, 29029 isn’t just an endurance event. It’s 36 hours of climbing, resting, eating, reflecting and catching up; we love this family ritual and always get something new out of it.
At the base of the first ascent, I thought about how I wanted this one to feel when it was over. The physical challenge is always there, but what I really wanted was to finish proud of how we approached it, how we treated each other, encouraged others, handled the moments that didn’t go as planned and whether we gave it our all.
Pride as Alignment
The pride I’m talking about isn’t about ego; I’m referring to pride that comes from alignment. When what we say, what we value, and what we do are in sync.
On the mountain, that might mean checking in on another climber or slowing down so that one of us could recover a bit. In leadership, it means making decisions that reflect our values, even when they’re not easy or popular. Pride, in that sense, is a compass; it helps us stay oriented toward who we want to be, even when conditions get tough.
The Power of a Framing Question
Somewhere around the sixth climb (of 17!), we started to notice the fatigue. The rain returned. Everyone found their own rhythm. Our conversations slowed a bit, and the only sounds were trekking poles striking gravel, the rain and the occasional word of encouragement. That’s when the pride question came back: How do I want to remember this?
That same question, “How do I want to remember this?” works beyond the mountain. It shifts focus from how things feel right now to how we’ll feel looking back.
When we ask this question, we’re really asking:
Am I acting in alignment with my values?
Will I respect how I handled this, regardless of outcome?
Does this reflect the kind of leader, parent, or person I want to be?
Is this goal big enough to matter?
Choosing the Story
Every climb, like every project or leadership experience, becomes a story we tell later. Pride is the compass that helps us write that story.
After about 32 hours, we finished, together and tired, muddy, and proud. Proud because we gave it everything we could. Proud because we showed up for each other. Proud because we lived it the way we wanted to remember it.
When this is over, this climb, this quarter, this milestone, how do you want to remember it?
With pride or with regret?