Saturday, October 17th, 2026

Saturday mornings have a different pace around here. Sheldon gets a longer walk. I don't open the laptop until I've had a second cup of coffee. And somewhere on that walk, whatever I've been chewing on all week usually floats to the surface.

This week it was three things. All of them, it turns out, are about the same question. Who's in the room with you, and who did you leave outside?

I moved to Orlando in March.

When you move to a new city in your forties, nobody hands you friends. There's no dorm. No new job with a break room full of people your age. You're a grown man with a small dog, a laptop, and a business to rebuild, and you have to go find your people on purpose.

I've done a fair amount of that. I host a marketing meetup here. I lead a men's accountability group that meets every Sunday night. I show up to things. On paper, I'm doing it right.

And still, a lot of the time, it's been harder than I expected.

Adam Grant's new book came out on Tuesday, and one idea from it has been rattling around my head all week. He says chemistry doesn't always develop quickly. Some of the strongest relationships start out lukewarm.

I read that and immediately thought about how many people I've written off after one conversation.

You know the move. You meet somebody, grab a coffee, and it's fine. Pleasant. Not electric. Nobody's finishing anybody's sentences. You walk away thinking, nice guy, probably not my person. And you never set up the second coffee.

I've done that more times than I want to count since March. And I'm starting to think I've been using the wrong test.

First coffees are weird. Both people are performing a little. You're giving your highlight reel. They're giving theirs. You're both a bit guarded, because you're strangers and that's normal. Of course it feels flat. Nobody's actually in the room yet.

The second coffee is different. You've got a thread to pick up. "How did that thing go that you were telling me about?" Now there's history, even if it's only three weeks old. Somebody remembered something. That's where it starts.

The third coffee is where you find out if there's anything there.

And most of us never get there, because we've decided chemistry is supposed to happen on the first try. Like friendship is a lightning strike instead of a slow build.

I don't think it is. I think it's more like training. The first run back is awful. Nothing about it feels like progress. If you judged running by the first mile you'd never run again. The fitness shows up later, after you've stacked a bunch of unremarkable days on top of each other.

There's one more piece I'm noticing in myself. Part of why I don't book the second coffee is that it feels like admitting something. That I want the friendship. That I'm the new guy who doesn't have his people yet. There's a version of pride that would rather look busy and self sufficient than look like it needs anybody.

That pride is expensive. It keeps you safe and alone at the same time.

And I think men in particular are bad at this. We'll call a guy back about a deal within the hour. We'll follow up on an invoice three times without blinking. But following up on a friendship feels needy, so we don't. We wait for it to happen on its own, the way it did when we were twenty two and everybody we knew lived within a few miles of each other and had nothing but time.

That world's gone. Nobody's coming to knock on the door and ask if you want to come out and play. If you want friends at this stage of life, you have to treat it with at least as much intention as you treat your pipeline. Which sounds unromantic. It's also true.

The irony is that the guys on the other side of that first coffee are usually feeling the exact same thing. Most of them would love a second coffee. They're just waiting for you to ask, because they've got the same pride you do.

Somebody has to go first. It might as well be the guy writing about it.

So here's what I'm doing. I'm going back through the last few months and writing down every person I had one good conversation with and never followed up. I already know the list is longer than I'd like. Then I'm sending a few of them the most unglamorous message in the world. "Hey, I enjoyed talking last time. Want to grab another coffee?"

That's it. No agenda. No pitch. Just the second coffee.

I'll let you know how it goes. Or I won't, and you'll know it went fine and boring, which is exactly how most good things start.

There's a Post Malone song I mentioned in yesterday's roundup called Wow. It's two and a half minutes of a guy looking around at his life and being openly pleased about it.

I've been playing it on repeat, and somewhere around the tenth listen it started to bug me. Not the song. The reason I needed the song.

I don't know how to enjoy a win.

I've gotten very, very good at surviving hard seasons. Give me a bad month and I'll grind through it. Give me a problem and I'll stay up with it. I know how to keep going when things are falling apart. That's a skill the last few years taught me the expensive way, and I'm grateful for it.

But when something actually goes right? I flinch.

A good week shows up and the first thing I do is look for what's about to go wrong. A client says yes and I'm already thinking about whether they'll renew. Something lands, and before I've even let it register, I'm onto the next thing. No pause. No moment. Just "okay, what's next."

For a long time I told myself this was discipline. Stay hungry. Don't get comfortable. Never celebrate too early.

I'm starting to think it's something else.

I think part of me believes I haven't earned the good stuff yet. That I'm still paying off something. That if I let myself enjoy a win in the middle of a rebuild, it'll get taken away. Like the universe is keeping score and I'm still behind.

Turns out it's fear wearing discipline's jacket.

And it has a cost I didn't see for a long time. When you never let yourself feel the wins, the whole rebuild starts to feel like nothing but hard. Every day is just another day of grinding. You lose the evidence that it's working. And then on the bad days, you've got nothing to stand on, because you never stored up any of the good ones.

The people who love you notice it too. They watch you hit something you've been working toward for months and react like you got a parking ticket. It's hard to celebrate with someone who won't celebrate with himself.

I don't have this figured out. But I'm trying something small. When something goes right, I stop for a minute. I say it out loud, even if it's just to Sheldon, who is a very supportive audience. "That went well." And I let it be true for a minute before I go find the next problem.

Grace covers the good days too. Took me longer than I'd like to admit to figure that out.

I've been watching the new season of Marshals, the Yellowstone spinoff where Kayce Dutton leaves the family ranch and becomes a US Marshal.

The whole premise is a fresh start. New job, new badge, a chance to be something other than John Dutton's son. And the season opens with the old life right back in the room. His son's in danger. His old loyalties are pulling on him. The ranch and the reservation and everything he's tried to step away from keep finding their way back in.

He changed the job. He didn't change who he is.

That landed harder than I expected, because I've done my own version of the fresh start this year.

New city. New place. A business I'm rebuilding from a different foundation than the last one. When I moved, there was a part of me that hoped the change of scenery would do some of the work. That I'd be a slightly different guy in a different zip code. More patient. More disciplined. Less of whatever I didn't like about myself back there.

That's not how it works.

The habits came with me. Some good, some not. The way I overcommit when I'm anxious. The way I go quiet when I should reach out. The tendency to measure my worth by how much I got done on a given day. None of that stayed behind at the old address.

But here's the part the show gets right, and it's the part I needed to hear.

The skills came too. Kayce isn't good at being a marshal in spite of his past. He's good at it because of it. The tracking, the instincts, the way he reads people. All of it came from the life he's trying to leave.

Same for me. Twenty five years of figuring out why people buy, how to say the thing clearly, how to build something from nothing. That came with me too. I'm not starting from zero. I'm starting with a whole lot of scar tissue, and the scars are the useful part.

And then there's the part about people.

The new life in that show only works because of who comes along. His son. His friends from the reservation. The old ranch hand who keeps showing up. Kayce was never built to do this alone, and the show knows it.

That's the one I keep coming back to. You don't start over alone. You start over with the people who were already in your corner, plus the ones you're willing to go find. The men in my Sunday night group. My daughters. The folks I'm still getting to know here. And I met someone not long after I got here, which has been part of this chapter too.

You can move cities. You can change careers. But the fresh start is still the same you, with the same skills and the same rough edges, choosing a new place to aim them. And if you're smart, choosing the people you'll aim them alongside.

Three versions of the same idea, really. Book the second coffee. Let the good days count. And stop pretending you have to start over by yourself.

If there's someone you had one good conversation with this year and never followed up, send them a message today. Nothing clever. Just the second coffee.

I'll be back tomorrow with three things I actually learned.

One step, one day. Grace over guilt. — Dan Kaufman