What if smaller is better?

On meeting people who built something small enough to belong and wondering why I haven't done the same.

Feb 12, 2026

Welcome to issue #055 of Unsubscribe. Each week, I send one essay to help you step off the default path and build a life you love, supported by work you enjoy.

A few years ago, Jennifer and I were relaxing inside a little wine bar in Lisbon, enjoying a glass of wine together on a sunny late afternoon.

It was a cool little spot called Senhor Uva, opened by a couple from Canada who moved to Portugal in 2019 with the idea of building a community around natural wine.

And it went well.

They created the kind of life you imagine when you daydream about leaving it all behind and starting over somewhere beautiful, affordable, and slower.

While I was sipping on a glass of rosé wine, I watched one of the owners, Marc, head out the front door to grab a case of wine from some other business down the street. And in the one hundred feet or so it took him to walk there, four different people stopped him.

They weren’t customers. They seemed to be neighbors who clearly knew him. From inside the window, I watched him navigate what looked like light and easy conversations. I’d imagine they were asking how he was doing or chatting about something that happened in the community. He wasn’t rushing at all. He was just there, being part of the neighborhood, and part of a place that wasn’t even his home country.

I sat there watching Marc, wine in hand, and felt something I didn’t expect.

Jealousy.

I wasn’t necessarily jealous of Lisbon or the wine bar or the sunny weather we were lucky enough to be blessed with that day. I was jealous of the fact that Marc and his partner Stephanie built something small enough that it let him enjoy his day in that way. That the people around him knew his name and stopped him on the street and wanted to chat. That his work and his community were interwoven.

I mentioned my observation to Jennifer on our stroll home that evening. About how rare that felt nowadays. About how we keep meeting people like this and walking away with the same strange feeling of jealousy.

Back where I live in New York, there’s a guy named Page who used to be the executive chef at Google in Los Angeles. He left that world and moved back to the Hudson Valley to open a little breakfast and lunch spot in Stone Ridge called Hash. It’s relatively small. It’s local. It serves really good, healthy food to people who live nearby. It’s a place where I meet my friends once a week, or stop by for an egg white wrap after I work out at the local gym.

When I talk to him about the community restaurant he’s built, he lights up. Not because the business is some $10M+ enterprise or because he’s got a crazy big expansion plan. He lights up because he loves running it. Because he’s part of something in his community that didn’t exist before he built it.

I think about the sushi chef Jennifer and I met in Sonoma a few weeks ago. A guy from Venezuela who walked into fifteen restaurants in Los Angeles looking for work, got rejected by fourteen of them, and eventually apprenticed under the one chef who gave him a shot. Now he runs a twelve-seat omakase bar in wine country, and he’s one of the happiest (and proudest) people I’ve talked to in a long time.

These people aren’t building massive empires. They’re building what I call “corners.” A little spot in the world that’s unapologetically theirs. Something small enough to care about deeply, and connected enough to actually feel like it matters.

Jennifer and I talk about businesses like these more than I’d like to admit. I’m obsessed with second mountain, small, community-driven places that meet a need and act as a gathering spot.

A bed and breakfast. A small wine bar. Something that would make us a real part of the community we live in, instead of just people who live there and work from home. We talk about it the way people talk about dreams they’re not sure they’re allowed to have.

And then we go back to our laptops and keep building the thing we’re already building.

There’s absolutely nothing wrong with what we’ve built. I love my work. I love writing. I love the people who read what I write, and I love that Jennifer and I get to do this together. I love the fact that I get hundreds of positive emails from people saying I’ve made an impact on their lives. But there’s something about the way Marc walked down that street in Lisbon that sticks in my mind because it makes me feel envy.

He wasn’t optimizing for scale. He wasn’t trying to reach more people or grow his audience or hit some milestone that would make him feel like he’d finally made it. He was just getting a case of wine and saying hi to his neighbors.

I think most of us know that community and connection matter more than revenue or followers or any of the metrics we track or brag about.

We know that the people who seem happiest aren’t usually the ones with the biggest businesses. They’re the ones who built something small enough to actually be present for.

But we often don’t choose it. Or at least, I haven’t, yet.

Part of me wonders if it’s because I don’t actually believe it. Like maybe I think I’m the exception, the one who can scale and still feel connected. Who can build something big without losing all of the small things that make it feel small, private, and intimate.

And part of me wonders if I’m just addicted to the game. The numbers going up, the audience growing, and the feeling of momentum. That stuff is hard to walk away from, even when you know it’s not the thing that actually makes you the happiest.

I don’t have an answer to all of this stuff I’m wondering about. I’m not going to pretend I’ve figured it out, because I haven’t yet. But writing it down, sharing it with folks, and hearing their stories has a way of helping me learn more.

I keep meeting people who chose the “corner” instead of trying to build an empire. And every time I do, I walk away feeling like they know something I don’t.

Or maybe they know something I know too, and I’m just not ready to act on it yet.

So here’s what I’m wondering this week:

Who’s a person in your life that built a “corner” business that makes you think, “Wow. That person knows how to live.”

What did they build, and why did it make you feel that way?

Reply and tell me. I read every response.

Thanks for reading, and I appreciate your time.

Who’s a person in your life that built a “corner” business that makes you think, “Wow. That person knows how to live.” What did they build, and why did it make you feel that way?

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