The Second Coffee

Since I moved to Orlando in March, I've written people off after one coffee more times than I want to admit.

Nice conversation. Nothing clicked and it wouldn’t turn into anything business wise. Never followed up.

This is the confession, the reason why, and the fix I'm running now.

When you move to a new city in your forties, nobody hands you friends.

There's no dorm. No break room. No twenty-two-year-old world where everybody lives a few miles away and has nothing but time.

You're a grown man with a dog, a laptop, and a business to rebuild. Everybody you meet already has a full calendar and a group text that's been running since 2011.

So 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 group. I go to church. I show up to things. On paper, I'm doing it right.

It's still been harder than I expected.

Meet somebody. Grab a coffee. It's fine.

Pleasant, not electric.

Forty-five minutes later we shake hands and say "we should do this again," and both of us mean it about sixty percent.

Then somewhere between the parking lot and my next call, I file them. "Probably not my person."

And I never book the second one.

An idea from Adam Grant's new book, Vibe, called me on it. Chemistry doesn't always develop quickly. Some of the strongest relationships start lukewarm.

I've been running the wrong test.

First coffees are weird. Two adults trying to decide in forty-five minutes whether to be friends. Both people performing. Highlight reel versus highlight reel. Both a little guarded.

Of course it feels flat. Nobody's actually in the room yet.

Every marketer knows the first email doesn't close. It takes multiple touches to build enough trust for a yes. We all know that about selling. Somehow I expected friendship to close on the first touch.

The second coffee is where there's a thread to pick up. "How did that thing go?" Somebody remembered something. The temperature of the table changes.

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

Most of us never get there, because we've decided chemistry is a lightning strike instead of a slow build.

It's more like training. After three meniscus tears, my first run back was awful. If I'd judged running by that first mile, I'd never have run again. Fitness shows up after you've stacked unremarkable days on top of each other.

So does friendship.

Seneca put it this way almost two thousand years ago: "Ponder for a long time whether you shall admit a given person to your friendship; but when you have decided to admit him, welcome him with all your heart and soul."

Go slow, then go all in. I'd been doing the opposite. Deciding fast, then going nowhere.

I had to ask myself why I don't book the second coffee. It's not a time problem. I schedule harder things than coffee every day.

The honest answer is that it feels like admitting something. That I want the friendship. That I'm still the new guy without his people.

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.

I've said this before and I'll keep saying it. Isolation was the soil every bad decision of my life grew in. I had people around back then. Nobody had the access. Everybody got the highlight reel. Nobody got the second coffee.

"Woe to him that is alone when he falleth; for he hath not another to help him up."

I know that woe. A second coffee isn't networking. It's making sure there's somebody close enough to notice when you fall.

We'll call a guy back about a deal within the hour. We'll chase an invoice three times without blinking. We'll send the "just circling back" email to a prospect seven times and call it persistence.

But following up on a friendship feels needy. So we wait for it to happen on its own, like it did when we were twenty-two.

That world's gone. Nobody's knocking on the door asking if you want to come out and play.

And I lead a men's group. I tell those guys they need people. Then I go home and don't send the text. That's the gap I live in, and this whole show is me reporting from it.

Here's the punchline I love.

The guy across the table is feeling the exact same thing.

He also walked back to his car thinking "probably not my person." He also didn't follow up, because it felt needy. Most of them would love a second coffee. They're waiting for you to ask, carrying the same pride you are.

A whole city of men with their hands in their pockets, waiting for somebody else to go first.

"A man that hath friends must shew himself friendly." That's an action, not a feeling. It's on the guy who wants the friends.

Somebody has to go first. Might as well be the guy with the podcast.

I'm good at networks. I've built them my whole career. A network is built on usefulness. A friend is the guy who'd notice if you went quiet.

When I moved here, I rebuilt the network fast, because I know how. I didn't rebuild the friends.

I think I was grading people on network logic. Is there a fit? An angle? When the answer was probably not, I moved on. Fine way to run a pipeline. Terrible way to find your people.

So the second coffee has one rule. No angle.

I'm going back through every month since March and writing down every person I had one good conversation with and never followed up on.

The list is longer than I'd like. I'll say that much.

Then I'm sending the most unglamorous message in the world:

"Hey, I enjoyed talking last time. Want to grab another coffee?"

No agenda. No pitch. No "I'd love to pick your brain." Just the second coffee.

And it's going in the floor, right next to the touches and the protein. One second coffee a week. Because it'll never happen if I leave it to feelings.

Friendship at this stage of life is a pipeline.

Same physics as everything else. It responds to follow-up. It dies from neglect. It compounds if you work it.

One second coffee this week. That's the floor.

Make your list tonight. Everybody you've had one good conversation with in the last six months and let drift. If they crossed your mind while you read this, they're on it.

Pick one. Send the message. Steal mine.

When you get there, pick up the thread. Ask about the thing they told you last time. Give one true sentence back that isn't the highlight reel. Before you leave, book the next one right there.

If they don't answer, follow up once. You'd do it for a deal.

Somebody has to go first. If you've been waiting for a sign, this is it.

Episode 23 is live now. The Second Coffee. The full story, including the one person I'm texting this week and how long my list actually is. Sunday's Reset is about what a perfect week did to my head.

One step, one day. Grace over guilt.