Saturday, October 31st, 2026

Happy Halloween.

Tonight the neighborhood will be full of tiny superheroes and princesses and at least one kid in an inflatable dinosaur suit who can't fit through a door. Sheldon will bark at every single one of them like they're a home invasion. He's seven pounds of security system and he takes the job very seriously.

I took him out early this morning before the street filled up with decorations and candy wrappers. Quiet loop, cool air, nobody else around. And the three things that had been rattling around my head all week finally sat still long enough for me to look at them.

All three are about the same thing, more or less. What we put on for other people, what drives us when nobody's watching, and who we're actually living for.

Halloween is the one night a year when everyone admits they're wearing a costume.

The rest of the year we just pretend we're not.

I've been noticing my own costume this week. It's not a cape or a mask. It's a sentence. "I'm good." Somebody asks how I'm doing, and before I've even checked, the answer's already out of my mouth. "I'm good, man. Busy. Good busy."

Sometimes it's true. A lot of the time it's a costume.

I was reading Shane Parrish's book Clear Thinking this week, which is in yesterday's roundup, and he names something he calls the ego default. It's the habit of protecting how you look instead of finding out what's true. When I read that, I thought about every time I've said "I'm good" because the real answer would have made me look like I didn't have it together.

The problem with the costume isn't that it's dishonest, although it is. The problem is that it works. People believe it. They stop asking. And then you've got a whole crowd of people who'd gladly help you, standing three feet away, with no idea you need anything.

I learned this the hard way when my life came apart. For a long stretch I was the most "good" guy you ever met. Totally fine. Handling it. And the whole time I was drowning in a way almost nobody around me knew about, because I'd put on such a convincing costume that they believed it.

What finally cracked it open was a small group of men who refused to accept the costume. The guys on my Sunday night calls don't let "I'm good" slide. They'll say, "Okay. Now tell me the real version." And the first few times that felt like getting caught. Now it feels like getting to breathe.

So I'm trying something this week, and I'll admit I'm not great at it yet. When someone I trust asks how I'm doing, I'm going to give them the real answer. Not a dramatic one. Just the true one. "Honestly, it's a heavy week, but I'm handling it." Or, "Better than last month. Still tired." Two extra seconds of truth.

There's a reason this matters beyond feeling better. When you wear the costume long enough, you start believing it yourself. You stop checking. You tell everyone you're good so many times that you forget to ask whether it's true, and then one day the gap between the costume and the guy inside it is so big you can't close it in a single conversation. Small honest answers keep the gap small.

You don't have to rip the mask off in front of everyone. Most people haven't earned that, and that's fine. But somebody in your life has. Give them the real answer.

Tonight the kids get to take their masks off when they get home. We should get that too.

The new season of The Terminal List dropped last week, and I've been chewing on the question it's built around.

What do you do after the list?

If you haven't seen it, the first season is about a Navy SEAL who loses everything and goes after every person responsible. Every scene runs on one fuel. Get the next name. Finish the list. And then he finishes it. And the thing that kept him moving is just gone.

I'm not a Navy SEAL. Nobody needs to worry about me going after anybody with a sniper rifle. But I recognized something in that setup that I didn't love.

When I started rebuilding, a lot of my fuel was anger and proof. Anger at what happened. A burning need to prove to people that I wasn't finished. That I could build something again. That they were wrong about me, or that I was wrong about me.

That fuel is powerful. I'm not going to pretend it's not. It got me out of bed on mornings when nothing else would. It got me through months where the work felt pointless.

But it burns dirty. And it runs out.

The thing about proving people wrong is that eventually you either do it or you realize they stopped paying attention a long time ago. Either way, the fuel's gone. And if that's the only thing in the tank, you're going to stall right in the middle of the road.

I can feel it starting to happen. Some days this fall, the anger just isn't there anymore. Which is good, honestly. I don't want to be angry forever. But it also left me with a quiet, slightly uncomfortable question. If I'm not doing this to prove something, what am I doing it for?

I've been sitting with that for a couple of weeks, and this is where I've landed for now.

The new fuel has to be something that doesn't run out when you win. Proving people wrong runs out. Money runs out the moment you hit the number, because then there's a new number. Applause definitely runs out.

What doesn't run out is the stuff that keeps going after you get there. Serving the people in front of you. Building something that makes someone's life a little easier. Being the kind of father my daughters are proud to talk about. Getting a little better at the work every month just because I love the work.

That fuel is slower. It doesn't give you the same rush at 5am. But it burns clean and it doesn't quit on you when the mission's done.

I've been running a little test on myself. Three questions, and you can do them on a walk.

If nobody ever found out I did this, would I still want to do it?

If I hit the goal tomorrow, would I keep going the day after?

If the people I'm trying to prove wrong disappeared, would the work still matter?

When I ran my own week through those, it got uncomfortable fast. A few things I'm doing passed easily. The book I'm writing passes every time. So does the client work, most days, because I genuinely like solving the problem in front of me. But a couple of things I've been grinding on this fall failed all three. They were proof projects wearing a business costume. I'm not dropping them overnight, but I'm not pretending about them anymore either.

If you've been running on anger or proof for a while, I'm not going to tell you to stop. It might be what's keeping you alive right now. Just know it's a booster rocket, not the engine. At some point it falls away. Make sure there's something underneath it.

The song on repeat this week is Love Letters to God by Nahko and Medicine for the People. It's ten years old now. They just put out an anniversary version, and I've played it more times this week than I'd like to admit.

The idea behind it is the one I can't shake. That a life can be a love letter. The work you do, the way you treat people, the way you spend an ordinary Tuesday. All of it addressed to somebody.

So I started asking a question that turned out to be harder than it sounds. If every day is a letter, who are mine actually addressed to?

I wanted the answer to be God. I wanted it to be my daughters, and the people I serve, and the guys in my group. And some days it is.

But if I'm being honest about a regular weekday, a lot of my letters are addressed to people who aren't even reading. The algorithm. Somebody who doubted me years ago. Some imaginary judge who's keeping score on whether I'm successful yet. A lot of what I do is written to an audience that doesn't exist.

That's a strange thing to admit in a newsletter, but I think it's true for a lot of us.

We spend our days writing to the wrong address, and then we wonder why it feels like nobody's writing back.

Faith, for me, has never been about getting the rules perfect. I've broken plenty of them. It's been about remembering who I'm actually talking to. When I remember, the whole day changes. I'm more patient on calls. I'm less worried about how a post performs. I'm kinder to myself when something goes sideways, because I know the one I'm writing to already knows the whole story and stayed anyway.

When I forget, everything gets louder and smaller at the same time.

I notice it most at night. On the days I've been writing to the wrong address, I lie there replaying how something landed, who saw it, whether it was enough. On the days I remembered who I was talking to, I just go to sleep. Same bed, same guy, same amount of work. Completely different night.

So this weekend I'm going to try something simple. I'm going to sit down with a pen and write an actual letter. Not a prayer I memorized. Not a polished journal entry. Just a plain letter, the kind you'd write to someone you love who you haven't talked to in a while. What I'm grateful for. What I'm scared of. What I'm sorry about. What I'm hoping for.

I don't know what's going to come out. That's sort of the point.

If faith isn't your thing, the exercise still works. Write it to the person you most want to be proud of you. Your kid. Your grandmother. Your future self in ten years. Just pick a real address.

Then look at your week and ask whether your days are going to the same place.

Three versions of the same question, really. Take the mask off for the people who've earned the real answer. Find a fuel that doesn't run out when you win. And make sure your days are addressed to someone who's actually reading.

This is week twelve of the forty seven I started on my birthday. Some weeks I feel like I'm making real progress. This one felt more like taking inventory. That counts too.

If you want a small version for the weekend, try this. Pick one of the three. Give one honest answer to someone who asks how you're doing. Or write down what's really fueling you right now, and whether it'll still be there in a year. Or write one letter, by hand, to a real address.

You don't need to do all three. One is plenty.

Tomorrow morning the clocks fall back and you'll get an extra hour. I'll be back then with three things I actually learned this week.

Enjoy the candy. Watch out for the inflatable dinosaurs.

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