Notes on Coffee Shops

I want to be upfront about something.

Most coaching philosophies make me uncomfortable. Not because the ideas are wrong, but because they're incomplete. They optimize for performance without asking what the performance is costing you. They talk about growth without being honest about what you have to give up to get it.

I've spent years trying to construct a philosophy I actually believed in. One that could hold the real questions: how do we build genuine stress tolerance, how do we have harder conversations, and maybe most importantly, does the work matter at all, or is it just about who you're doing it with along the way?

I couldn't find that version of this work anywhere else. So I built it.

After a decade in tech and several more years training as a clinical therapist, I kept arriving at the same conclusion: the gap between good leaders and exceptional ones isn't strategic. It's internal. And closing it requires a different kind of conversation than most organizations know how to have.

What follows is my attempt to write down what I actually believe: about leadership, about pressure, about the things that matter and the things we've convinced ourselves matter when they don't. I've organized it around coffee shops, because they have always been my sanctuary from the chaos of the world. The place I go to slow down, create distance, and see things clearly.

That, it turns out, is also the work.

There is a coffee shop in Kyoto called Sunny George.

I walked in not knowing anything about it. It was early, I was jet-lagged, and I needed somewhere quiet to sit with an espresso and let the city come into focus slowly. Behind the counter was a man I'll call Kenji, and on a small shelf near the register was a brewing device I had never seen before. I'm a coffee nerd, so I asked about it.

What followed was one of the more remarkable conversations I've had with a stranger.

Kenji had designed and built the device himself. He'd spent a career as an industrial designer, living across three continents, making objects that balanced utility with beauty. The coffee bar I was leaning on, he made it. The espresso machine behind him, he'd modified it. The light fixtures overhead, the stools, the handles on the cabinet doors. Every inch of that shop had passed through his hands. He had built the place the way a person builds something when they believe the details are important.

We talked for an hour. About design, about craft, about his family, about the specific kind of loneliness that comes with spending your life making things most people will never notice. By the time I finished my coffee I knew things about this man that his colleagues probably didn't.

None of that happens if I don't slow down. If I don't notice the device on the shelf. If I don't ask the question.

This is, I've come to understand, the thing I do. I slow down in rooms where everyone else is moving fast. I notice what's sitting quietly on the shelf. I ask the question that isn't being asked. And I've found, consistently, that when someone feels genuinely seen, not evaluated or managed but actually seen, something opens up that makes the real work possible.

That's what coffee shops taught me. And it's what I try to bring into every engagement.

There's a particular kind of crisis I see often in high-performing leaders.

It doesn't announce itself as a crisis. It shows up as a short fuse in a Tuesday afternoon meeting, or a compulsive need to be in every decision, or an inability to sleep through the night before a board review. From the outside it looks like intensity. From the inside, it feels like the walls are closer than they used to be.

What's almost always underneath it is this: somewhere along the way, the work became the self. Not consciously. Nobody decides to do this. But the hours compound, the stakes get higher, the identity gets built, and eventually your self-worth and your quarterly results are residing in the same place. Which means every piece of critical feedback is an existential event. Every missed target is a referendum on your value as a person.

This is a fragile way to operate. And it gets more fragile the higher you go.

When I sit in a coffee shop, I am practicing something deliberate. I am creating distance between myself and whatever I was just inside of. The warmth of the cup, the smell of the espresso, the low hum of other people living their lives. It pulls me out of the tunnel and back into the broader fact of being alive. My problems don't disappear. They just get appropriately sized.

That's what I help leaders do. Not abandon their ambition or care less about the work. But build enough distance to see it clearly. To hold it in one hand rather than letting it hold them. To understand that who you are is larger than what you produce, and that operating from that understanding builds resilience.

I almost didn't ask about the device on the shelf.

I noticed it. I was curious about it. And then, for a half-second, I did the thing most of us do in unfamiliar situations: I thought, interesting, and moved on.

The habit of skipping past our own curiosity is so ingrained we barely notice we're doing it. And in leaders, this habit gets reinforced by every incentive structure around them. You are paid to have answers. You are evaluated on certainty. You are promoted because you project confidence. And somewhere in that process, the admission of not knowing starts to feel like a liability.

It isn't. It's the most powerful thing you can model.

"I don't know," said plainly, without apology, without immediately filling the silence with a pivot to what you do know, signals something most organizations are starving for. It signals that the people around you are allowed to not know either. That uncertainty is information, not weakness. That the goal is to figure it out together rather than perform competence until someone cracks.

The leaders I work with who are most stuck are almost always the ones most invested in being right. Not because they're arrogant, but because the pressure to be excellent has made them afraid of what the alternative looks like. Sharing uncertainty feels like exposure. So they stay certain, and the people around them stay silent, and the problems that needed a real conversation keep not having one.

Most organizations say they value feedback. Almost none of them mean it.

What they value is feedback that arrives at the right moment, in the right packaging, with the right amount of diplomatic cushioning so that nobody has to feel genuinely uncomfortable. Which means the feedback that would actually change something, the direct and specific and slightly uncomfortable kind, either never gets said, or gets said so softly it doesn't land.

This is not a kindness to the people it's meant to protect. It's a slow tax on their development.

In coffee shops, I watch people have hard conversations all the time. A couple negotiating something real. A parent and an adult child sitting with old tension. Two friends trying to get back to something they lost. What strikes me, every time, is how rarely these conversations end badly. More often they end with something visibly loosening in both people. The thing that felt dangerous to say turns out to be the thing that needed saying. The discomfort was the doorway.

Part of my job is to help leaders have those conversations: with their teams, with their peers, with themselves. And part of it is helping organizations build the conditions where those conversations can actually happen. Where vulnerability isn't punished, where not knowing is safe, where someone can say "I'm struggling with this" without it becoming a career event.

That's not softness. That's the structural requirement for building a team that doesn't have a ceiling.

This one is harder to say, so I want to say it plainly.

Your work is not the most important thing in your life. The meetings, the metrics, the org design debates, the quarterly planning cycles. None of it, in the long run, is what you will care about most. This is not an argument for caring less or performing worse. It's an argument for understanding what the work is actually for.

In my experience, the answer almost always comes back to people. You work hard because you want to provide something for someone. Because you want to build something that matters to the people using it. Because you are trying to become a version of yourself that you can be proud of in front of your family, your mentors, the people who believed in you early.

The work is a mechanism. It is not the destination.

When I watch the man in Kyoto sit down with a stranger and spend an hour talking about design and family and the texture of a well-made life, he is not talking about his KPIs. He is not talking about market share or competitive positioning. He built every inch of that coffee shop because he believed beauty was worth the effort. And the most meaningful part of his day was the conversation.

The leaders who figure this out, who locate their work inside a larger context of meaning rather than letting the work be the context, are the ones who last. They make better decisions under pressure because their self-worth isn't on the table in every negotiation. They build better teams because they're genuinely interested in the people, not just the output. They lead with a kind of groundedness that can't be manufactured by a framework.

I'm not here to help you care less about winning. I'm here to help you understand why you want to win, and whether the version of winning you're chasing is actually the one that matters to you.

Because at the end of it, what you'll remember isn't the quarter you hit your numbers. It's the people you built something with. The conversations you were brave enough to have. The moments where you slowed down long enough to notice what was actually there.

Everything else is just the shelf. What matters is whether you asked about the device on it.