Go Play Hooky
The most important meeting on your calendar has no agenda, one attendee, and no wifi.
I was talking to a ski industry executive not long ago. Asked him how the skiing was in his valley this winter. He laughed and said he didn’t know - he never has time to get on the mountain anymore. He meant it as a joke. I’ve heard that joke too many times for it to be funny. The cobbler’s children have no shoes. And apparently, the ski exec doesn’t ski.
I’ve been that guy. More than once.
There’s a version of you that existed before all of this.
That version woke up on a Tuesday and drove to the trailhead before anyone else was up. Fished a stretch of water that required a hike to reach. Skinned up a mountain in the dark to be first on the powder. Walked the dog so far that the dog gave out before you did.
Nobody put it on a calendar. It was just life.
Then you started a company. Or got named line manager. Or got the promotion you always thought you wanted. And the calendar filled in from the outside — someone else’s needs, someone else’s timeline, someone else’s urgency stacked on top of yours. Tuesday became a standing call. The trailhead became a someday. The dog walk became a loop around the block.
This is the slow leak that nobody warns you about. Not burnout exactly. More like drift. You’re still working on something you believe in, still moving fast, still useful to people — but you’ve gradually stopped doing the things that made you the person who could do any of this in the first place.
Here’s what I’ve learned, and what I now tell the founders and executives I work with:
Your calendar doesn’t lie. If it’s not on there, it doesn’t happen.
Not because you’re lazy or don’t care. Because the world has infinite legitimate claims on your time and exactly zero of them will voluntarily make space for you. That’s not a character flaw in the people around you. It’s just how it works. The only person who will schedule you is you.
So schedule yourself. Not a vague intention — a specific event, with a specific time, in a specific place:
Thursday, 6:15am. Emerald Mountain trail system. Two hours on the bike. Tires on dirt by 6:20, back at the office by 8:30.
Wednesday. First chair at Steamboat. No phone, no Slack until you’ve got 5,000 vert in your legs.
Tuesday evening, 4pm. Sarvis Creek Wilderness. Waders on, rod rigged, on the water by 5. Not a webinar. Not a quick call first. On the water by 5.
Friday morning, 7am. Mad Creek trailhead with the dog. Four miles minimum. Not a dog walk. An actual hike.
Schedule it like a meeting with a VIP — because it is. The VIP is you. Give it a title, a duration, a location. Protect it the way you’d protect time with your most important investor. Because the person who shows up rested, grounded, and still connected to why they built this thing? That person is worth protecting.
You’re allowed to cheat. Kid has a soccer game — go. Friend needs help — go. The pipes burst, the flight got moved, life showed up uninvited — go deal with it. The point isn’t perfect attendance. The point is that when a supplier wants to meet Monday morning at 10, you’re looking at a calendar that already has something on it. Something that matters. That gives you a moment to actually weigh it — is this meeting worth moving? Can it wait until afternoon? Does it need to happen at all? Without the block, there’s nothing to weigh. The default is always yes, and yes always means the outdoor thing loses. If you do cancel it, put it back. Not someday. That week.
I wrote this originally for the founders and executives I work with — but the drift doesn’t care what your title is. You don’t have to live in the mountains for this to work. You don’t have to live somewhere with a trailhead out the back door. And you don’t need a flexible schedule — if you can’t find the time in your 9-to-5, find it in your 5-to-9. You just have to remember where you used to find joy — and make it part of your job to get back there. Once a week, at the very least. The specifics are yours. The discipline is universal.
When you do keep the appointment — and you will, more often than you think — keep it fully. Don’t show up with your phone in your hand. Don’t cut it short for a quick sync that isn’t. Don’t half-ass it with one eye on your messages. Nobody can Zoom into a tailwater. The powder doesn’t wait.
That boundary isn’t selfishness. It’s maintenance. You are the asset. Whatever you’re running — the business, the shop, the family operation, the team — it runs on your judgment, your energy, your pattern recognition, your relationships. All of those things degrade without input. The input, for people like us, is time outside doing hard and beautiful things.
The best investment decisions I’ve made, the clearest writing, the sharpest founder conversations — they almost all happened after time on the water or on the mountain. Not after another hour at the desk. This Substack exists because of those hours. The ideas don’t come to me at my desk.
A lot of people I know in the outdoor industry — founders, brand managers, sales reps, buyers, athletes turned executives — got into this because they were, first and foremost, people who lived outside. The work came later, as a way to stay close to that world, to build something that mattered in it.
The irony is that success can pull you indoors. The more the operation grows, the more it needs from you, and the easier it is to let the thing that started all of this quietly fall away.
Don’t let that happen. The founder who fishes is a better investor in fishing companies. The entrepreneur who rides trails understands trail culture in a way no market research can replicate. The skiing CEO shows up to the buyer meeting with something you can’t fake — they can tell you actually live this life.
That’s your edge. Protect it.
Before you close this tab, open your calendar and put the thing in. Whatever your thing is. The ride, the run, the river, the ridge. A specific day. A specific time. A specific place.
Keep the appointment. The version of you that shows up will remind you why you built any of this in the first place.
I’m Andrew Luter, founder of Rio Chato Investments. We back early-stage outdoor recreation and lifestyle brands — the kind of companies building gear and experiences for people who’d rather be outside. I’m based in Steamboat Springs, Colorado, which is basically a full-time reminder of why this space matters.