I just got back from a week in Tokyo with a group of guys I’ve been meeting with for years.
We’re part of what’s called an Entrepreneurs’ Organization (EO) forum, a small group of business owners who meet monthly for four hours and do an annual retreat together. I joined because I wanted to grow my business. I wanted to be around other founders who understood the challenges I was facing. Friendship wasn’t really on my radar. I had that covered. Or at least I thought I did.
But somewhere along the way, this group became something I wasn’t expecting. And I didn’t fully realize it until I went through the hardest period of my life a few years ago. Several members showed up for me in ways that few others did. Before EO, my friend network was mostly coworkers and neighborhood friends. Great people. But we’d never built the kind of depth that a crisis demands, and that was on me as much as anyone. I wasn’t sharing my bottom 5% with them either. Those friendships just weren’t structured for it. This group was. And the difference was impossible to ignore.
The structure is simple: everything shared stays in the room. You bring your top 5% and your bottom 5%, the highest highs and the hardest lows, and the group shows up for all of it. They challenge you, celebrate with you, and hold you accountable. No advice unless you ask for it. No judgment. Just presence and honesty.
This organization is built for entrepreneurs. But I don’t think the structure needs to be. The confidentiality, the commitment to showing up, the rhythm of meeting regularly, the expectation of honesty. That framework could work for almost anyone. A group of teachers. Neighbors. Old college friends who’ve scattered. The label doesn’t matter. The infrastructure does. And that’s what I keep coming back to.
A pattern worth noticing
During the retreat, we did a variation of psychologist Arthur Aron’s famous “36 Questions” exercise. In 1997, Aron found that when two people answer a series of increasingly personal questions together, they build closeness fast. The key was gradual, reciprocal self-disclosure. Start light, go deeper, take turns. We paired off one-on-one and worked through our own version, moving from easy questions into more personal territory within the same conversation. By the end, I knew things about people I’d been meeting with for years that I’d never thought to ask about.
But those kinds of exercises were maybe four hours of our week. The rest was go-karts through the streets of Tokyo, ninja training, food tours through unfamiliar neighborhoods. Shoulder-to-shoulder stuff. And the conversations that happened in between, walking from one place to the next, throwing out questions in the back of an Uber, sitting around a table after an experience, those were often the moments that mattered most.
I know how fortunate I am to be able to do something like this. A week in Tokyo is a luxury of both time and money, and I don’t take that for granted. We’ve done retreats domestically that were just as meaningful. The location isn’t what makes it work. What matters is the container: the people, the commitment, and the sustained time together. You could do this at a cabin two hours from home.
Because there’s something that happens when you spend several consecutive days with people that a monthly meeting can’t replicate. You see how someone gets ready in the morning. How they navigate a crowded train station. How they interact with a waiter who doesn’t speak their language. Ordinary human behavior you’d never witness in a structured setting. And it changes how well you know someone.
I became genuinely close with one of our newer members over the course of the week in a way that months of meetings hadn’t accomplished. We’d been cordial in our regular sessions, but this trip is where the friendship actually took shape. Not because of any single conversation but because the sustained proximity gave the relationship room to breathe. That’s hard to manufacture in a four-hour meeting once a month.
And I’ve seen what happens when someone in this group goes through a real crisis and the others show up for them. When the structure you’ve built together becomes the thing that carries you through the hardest chapter of your life.
Those two realities sit side by side in my mind. The friendships still taking shape and the ones that have already been tested. Both of them reinforcing the same thing: this stuff matters, and it rarely happens on its own.
Something to ask yourself
Do you have a space in your life where vulnerability is expected and showing up is non-negotiable?
I’m not talking about a group chat that goes quiet for weeks or a friendship held together by good intentions and “let’s get together soon.” I mean a place where the structure itself creates the conditions for depth. Where confidentiality is assumed, honesty is the norm, and you walk away better for having been there.
Most of us don’t. We have friendships that are real but unstructured. Full of warmth but no rhythm. And without that rhythm, even the best friendships tend to drift.
Engineer a collision this week
I’m not going to pretend you can build something like this overnight. It took years for our forum to become what it is now, and we still check in on how it’s going and set goals for the group together every year. This stuff takes maintenance.
But I do think most people are one conversation away from starting.
Think about two or three people in your life and ask yourself: would they show up if I proposed something regular? Not a one-time hangout. Something with a rhythm. Even just quarterly.
You might be surprised by the answer.
This is something I plan to write a lot more about, both here and in the book I’m working on. How to build these kinds of groups. What makes them work. What makes them fall apart. The exercises, the structure, the ground rules. Because I think this might be one of the most important things we can do for our friendships, and almost nobody is talking about how to actually do it.
More on that soon. For now, maybe just sit with the question:
Who would you want in the room?
