Old Friends in New Places: What Skiing in Japan Reminded Me About What Actually Matters

The five of us have known each other for most of our lives. For some of us, 45+ years. We grew up together in Seattle — the kind of friendships that were formed before anyone had a career, a title, or a reason to impress anybody. We're all in our forties and fifties now, all still married, all fathers, all professionally established. Between the five of us we cover venture capital, real estate development, capital markets, scientific research, and entrepreneurship. We are, on paper, exactly the kind of peer group looks like they have it all figured out.

But that's not what we talk about when we're together. Not really.

Who These Men Are

When you've known someone since before they graduated elementary school, you know things about them that their colleagues never will. You know about the crazy ideas they had.  You know about the ex-girlfriends.  The angsty John Hughes like moments that made us who we are.  You know the version of them that existed before the roles they now occupy with such apparent ease.

Relationships like these are a rare thing to have in your forties and fifties. Most of the relationships you form after a certain point are contextual — business, neighborhood, kids' school. Those friendships are real, but they're built around a shared present. These friendships are built around a shared past and, because we keep showing up for each other, a shared future too.

Japan was the first time the five of us had traveled internationally together as a group, and the first time we had been all together in at least 20 years. We had skied together domestically, had dinners, zoom calls, and partial group reunions over the years, but this was different. Ten days, two islands, planes, trains, and automobiles — the kind of trip that tests whether people can actually be in close quarters without it becoming work.

The answer was yes, effortlessly. And I think it's worth pausing to think about how to nurture that.

A Shock on Day 4

On the fourth day of the trip, one of our group got news from home. His mother, back in Seattle where we all grew up, was seriously ill. He needed to go back.

He left that day.  

There wasn't much to say about it at the moment. We helped him through a few decisions, waited with him while he figured out logistics, then he was off.  The mountains were there, the snow was there, and he was leaving.

After he was gone the four of us skied that day, but it was quieter. Not sad exactly — but certainly somber. The trip continued, as trips do, but there was a shape to the rest of it that hadn't been there before. We talked about our parents more than we had in years. We talked about Seattle. We talked about what it means to be in your forties and fifties and watching the generation above you get older.

None of that would have happened on a zoom call or over a stopover in each of our respective cities. It happened because we were there — in person, in the mountains, with nowhere else to be.

On Career and Transition

The five of us are at different places professionally, and part of what made this trip interesting was the honesty about that. One of the group is navigating a significant transition in his work — the kind of in-between period where what you used to do has ended and what comes next isn't fully formed yet. Another is running faster than ever, building something at a pace that leaves almost no room to think. Another has found a kind of stability that looks easy from the outside but costs a lot to build.

We talked about all of it. On chairlifts, over dinner, walking back from a temple in Tokyo on a cold morning. The kind of conversation that can happen when people aren't performing for each other — when you're just talking because you trust the people in the room.

I've been in a lot of peer groups and advisory relationships over the years. I've done the structured forums, the peer circles, the facilitated retreats. They have value. But there's something that happens between old friends on a trip that no facilitated process fully replicates. The time together, the shared physical experience, the absence of any agenda — these create conditions for something more honest.

What I'm Taking With Me

I came home from Japan thinking about the difference between the relationships we maintain and the ones we actually invest in. Maintaining a friendship looks like responding to texts and making it to the occasional gathering. Investing in it looks like going to Japan together for ten days and making room for the real stuff. And making sure that each person contributes to the plan - choosing a hotel, a ski resort, a restaurant, an outing.

These men are people I want to keep investing in. Not because of their professional networks or what they can offer me — but because they've seen me at my worst and my best, because they tell me the truth, and because standing at the base of a mountain in Hokkaido with them felt like exactly where I was supposed to be.

One of them had to leave early to be with his mother. That was hard. But it was also a reminder that showing up — really showing up — is the whole thing. In friendship, in family, in business.

The mountains will always be there. The people, less so.