Saturday, October 24th, 2026

Sheldon and I took the long loop this morning. He weighs about seven pounds and he walks like he owns the neighborhood, which in his mind he does. Cool air for once, which in Orlando in late October feels like a gift. And somewhere around the halfway point, the three things I'd been chewing on all week lined up in a way I didn't expect.

All three are about the same guy. The one I used to be, and what I'm supposed to do with him now.

There's a song I mentioned in yesterday's roundup called WHO I WAS, by NF and mgk. It's been on repeat for two weeks. Two men, a stripped down beat, and a whole lot of honesty about the people they were before.

What struck me is that neither of them is trashing his old self. They're not doing the thing where you look back at your past and spit on it. They're just looking at it. Naming it. Sitting with it. The anger, the grief, the choices that cost them. They don't pretend it didn't happen and they don't pretend it defines them either.

I've been doing the spitting thing for a while.

When your life comes apart, and mine did, there's a strong pull to draw a hard line. The old me over there, the new me over here. Everything before the line was a mistake. Everything after is the real version. It feels clean. It feels like progress.

It's actually a trap.

Because when you disown the guy you used to be, you disown everything he built too. The skills. The instincts. The twenty five years of learning why people buy and how to say things clearly. The relationships he started that are still alive. All of that came from him. If he's the enemy, then half of what I'm rebuilding with is contaminated, and I'm walking around ashamed of my own toolbox.

And here's the other cost. If I can't look at him with any grace, I can't learn from him either. You can't study something you refuse to look at. So the mistakes stay blurry. And blurry mistakes have a way of repeating.

So here's where I've landed, at least for this week.

The man I used to be doesn't get the keys. He doesn't get to drive. Some of his habits were expensive and I'm not going back to them. But he's not a stranger and he's not a villain. He's the guy who got me here, scars and all. He made some bad calls with the information and the wounds he had. He also did a lot of things right that I've been too proud to give him credit for.

I tried something on Wednesday night that I'd recommend if you've been at war with your past. I took a legal pad and drew three columns.

What he got right. What he got wrong. What I'm keeping.

The first column was longer than I expected. That surprised me. The second column was about what I thought it would be. The third one was the most useful thing I've written in a month, because it turns out I'd been throwing out good stuff along with the bad just to feel like I'd changed.

You can be done with who you were without hating him. In fact, I'm starting to think you have to. Grace isn't only for the man you're becoming. It's for the one you're leaving behind, too.

I listened to an Ed Mylett episode this week where he breaks down the stages of getting good at anything. His version is that every pursuit starts out ugly, then gets awkward, and then eventually starts to mesh. And he says the awkward stage is where most dreams quietly die.

I laughed out loud when I heard that, because I took inventory on the walk this morning and I'm in the awkward stage of basically everything.

The book I'm writing is in the awkward stage. I'm aiming for a finished first draft by the end of the year, and right now it's past the fun part, where every idea felt electric, and nowhere near the part where it reads like a book. It's a pile of chapters that each make sense on their own and don't quite talk to each other yet. Some mornings I sit down and it flows. Other mornings I write four hundred words and delete three hundred and eighty of them.

My running is in the awkward stage. I've been back at it since September, after the knee sidelined me for a stretch this summer. It's not ugly anymore. The first few weeks were ugly. Now it's just awkward. Some days I feel like a runner. Some days I feel like a guy who bought shoes.

The new workout routine I started a few weeks ago is awkward too. I know the movements now. I don't need the notes on my phone. But it isn't automatic yet, and every morning there's still a small negotiation in my head about whether today's the day I skip.

And the business, the real one, the rebuild, is in the awkward stage in a bigger way. It's not starting from scratch anymore. Things are working. But it doesn't have the smooth, quiet hum of something that runs on its own. I still feel every gear.

Here's what I'm realizing about the awkward stage. It's harder than the ugly stage in one specific way.

In the ugly stage, you expect to be bad. Nobody's embarrassed by their first week of anything. Being lost is just part of the deal. You've got a built in excuse.

In the awkward stage, the excuse is gone. You've been at it long enough that you feel like you should be better by now. You can see what good looks like. You can almost touch it. And you're not there. That gap between what you can see and what you can do is the most frustrating place on the whole map.

That's where people quit. Not at the start. In the middle, when it's not new anymore and it's not good yet.

And I think there's a sneaky reason for it that ties back to the first thing. In the awkward stage, the old version of you starts to look really attractive. At least he was competent at the old stuff. At least he knew what he was doing. The awkward stage makes you homesick for a guy you already decided not to be.

I'm not going back. But I'm also done pretending the middle should feel better than it does. Awkward is the price of the next level. It's not a sign you're doing it wrong. It's a sign you're doing it.

So my plan for the middle is boring. Keep showing up. Keep the bar low enough to clear on a bad day. Five hundred words on the book, even if I delete four hundred of them. One run, even if it's slow. The workout, even if it's half the weight. And stop checking the mirror every morning to see if I've arrived yet.

Ed's line was that you're making more progress than you think. I don't know if that's true for me. But I know the only way to find out is to stay in the awkward stage long enough to come out the other side.

The new season of The Diplomat dropped last week, and there's a line in the teaser that I haven't been able to shake. Kate Wyler tells her husband she's not trying to get out of the marriage. She's trying to get back in.

I want to be careful here, because this isn't a column about anybody's marriage. But that sentence applies to a lot more than marriage, and it's been working on me all week.

When something we committed to gets hard, the easy move is to find the exit. Quit the group. Drop the habit. Let the friendship go quiet. Stop going to church because you missed three weeks and walking back in feels awkward. Abandon the project because it's in the awkward stage and something new looks shinier.

Getting out has a script. Everybody knows how to leave. You just stop showing up and let silence do the work.

Getting back in doesn't have a script. You have to walk back into the room. You have to face whatever happened while you were gone. You have to admit you drifted. And you have to choose the thing again on purpose, which is a lot harder than choosing it the first time, because now you know exactly what it costs.

That's the same idea mgk raps about on the song from the first thing, from a different angle. He hid from God for more than twenty years, and when he came back, nobody made him explain himself. He wasn't asked to prove he still qualified. He was just welcomed home.

I know that story. It's the prodigal son. The kid takes his inheritance, blows all of it, and hits bottom. He writes himself a whole speech on the way home about how he's not worthy and how he'll work as a hired hand. And the father doesn't even let him finish. He sees him coming from a long way off and he runs.

The thing about that story is that the hardest part isn't the coming home. It's deciding to start walking.

I've drifted from some things in the last few years. Some people. Some habits. If I'm being honest, some of my faith. Not all at once and not on purpose. It's the slow kind of drift, where you look up one day and you're further from shore than you remember swimming.

Some of it I'm walking back toward now. The men's group on Sunday nights is part of that. Being in church is part of that. A couple of phone calls I've finally made to people I let go quiet are part of it too. Every one of those walks back in felt more awkward on the way there than it did once I arrived. Nobody asked me for the speech. Most people were just glad I came back.

So that's the one I'm sitting with this weekend. Is there something you've been drifting away from that you actually want back? Not something you should want. Something you do want.

If there is, you don't need a big announcement or a perfect reentry. You don't need the speech. You just need to start walking.

Three versions of the same idea, really. Stop trying to bury the guy you used to be. Stay in the awkward stage long enough to get through it. And when you've drifted, choose getting back in over getting out.

This is week eleven of the forty seven I started on my birthday. I'm not where I want to be. I'm also not where I was. On most days, that's enough.

Here's your small version for the weekend. Pick one thing you've drifted from that you actually want back. A person, a practice, a place. Make one move toward it before Monday. A text. A visit. Ten minutes.

You don't have to finish the walk this weekend. You just have to start it.

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

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