Chart Your Own Path: Hiking Lessons From Vail
“Comparison Is the Thief of Joy.” - Theodore Roosevelt
A few weeks ago, I tackled two of the hardest hikes of my life - at least since the epic climb I once did at Mount Aspiring in New Zealand.
After attending the Bridging the Gap Conference (which I absolutely loved, by the way - you should go!), I headed up to Vail, CO, for a couple of days of solo downtime.
I’ve been going to Vail for nearly 40 years—but always in the winter for skiing. This was my first time seeing it in the summer, and it was magical. I stayed in a little cabin on the river, cooked great meals, and soaked up the nature. But the real adventure was waiting on the trails.
The Hikes
I pushed myself on two of them. Hard.
Berry Picker Trail – About eight miles, much of it straight uphill, starting above 9,000 feet in elevation. I tacked on a couple of extra trails for good measure, making it a real lung-burner.
Booth Lake Trail – Around ten miles, with the kind of long, sustained climb that tests not just your legs but your grit.
Gore Valley Path – My “rest day” hike. Seven miles, mostly flat, winding, scenic, weaving through Vail Village and along the cascades. Lovely in its own way, a nice breather between the big climbs.
Each trail challenged me differently, but I kept going. And by the end of those three days, I felt both exhausted and exhilarated.
For me, these were hard hikes. For some of my friends, those hikes might have been “no big deal.” Eight or ten miles at altitude? Just another day. For others, these hikes might be unimaginable right now.
That’s the lesson I carried home:
Don’t compare yourself to others
What’s hard for you might be easy for someone else
Celebrate what’s hard for you
What’s impossible for someone else might be your victory
Keep pushing yourself to grow, without diminishing your wins
Maybe someday I’ll hike as easily as more seasoned mountaineers. Maybe not. But I’m proud of what I did, and that pride is enough.
Don’t let comparison steal your joy
My single hardest hike ever (it was a run, actually) was one where an Ironman friend of mine challenged me (a full Ironman competitor, which is just effing crazy). The Grouse Grind in Vancouver, on the face of it, didn’t seem like a big deal. About two miles long, at sea level, it seemed like no big deal in my mind. I’m a trail runner and I can easily knock off a 7.5K in the hilly area where I live. So I’m game, and no matter what, I’m gunna keep up with Dave (who lives at the base of The Grind and does it almost every day btw…).
We have been lifelong friends and have challenged each other since we were teens on trail runs, backcountry skiing and waterskiing; taunting and pushing each other. The short version is I wasn’t far behind him, but I was barfing (yes, really) and wheezing, and my legs were burning. I was super proud of myself, but it was a lesson for me that I was done trying to prove my mettle to someone so far ahead of me in skills.
Chart your own path. Be proud of what you can do today. Keep pushing yourself to grow - but celebrate the hard things you’ve already achieved, no matter how they stack up against someone else’s.
Whether in hiking, business, or life, you’re not running someone else’s race. You’re walking your own trail. And that’s where the magic happens.
