Sunday, October 18th, 2026

This was a quieter week. No race on the calendar, no big launch, nothing dramatic to report. Just work, walks, and a lot of time in my own head.

A slow week has a way of showing you what you were too busy to notice. When there's no big deadline to hide behind, you find out which habits were real and which ones were just riding the adrenaline. That's useful information, even when it's a little uncomfortable to look at.

All three of these came out of that kind of noticing. None of them are complicated. All three changed something about how I'm running next week, which is still the only test I care about for this letter.

I listened to Spencer Greenberg on Modern Wisdom this week. He's the guy behind ClearerThinking.org, and he's read more self help books than anyone should have to. The episode is basically him sorting the advice that holds up from the advice that doesn't.

One idea from it has been stuck in my teeth all week. He talks about what he calls "glad you did it" activities.

The simple version, at least the way I understood it, is this. There are things that are fun while you're doing them. And there are things you're glad you did once they're over. Sometimes those overlap. A lot of the time they don't.

Scrolling is fun while you're doing it. Nobody has ever closed an app after forty minutes and thought, I'm so glad I did that.

A hard workout is usually not fun while you're doing it. Almost nobody finishes one and regrets it.

The call you've been dreading. The honest conversation. Cleaning out the inbox. Writing the first ugly page of something. Walking the dog when it's still dark out. Not fun. Glad I did it, every time.

Once I heard it framed that way, I couldn't stop seeing it.

I tried running my week through that filter in my head. Things I enjoyed in the moment on one side, things I was glad I'd done by the end of the day on the other. The overlap was smaller than I'd like. And the "fun but not glad" column was doing real damage. Nothing dramatic. Just an extra half hour here, a rabbit hole there, adding up to a day that felt busy but left me with nothing to point at.

Here's what I'm changing.

The "glad I did it" stuff goes first. Before the inbox, before the phone, before anyone else's priorities get a vote. Not because I'm some productivity monk, but because those are the things my evening self will thank me for, and my morning self is usually the only one with enough willpower to do them.

And I'm using a new question when I'm deciding what to do next. Not "what do I feel like doing?" That one's easy to rationalize. Instead, "at nine o'clock tonight, will I be glad I did this?"

That question is annoyingly hard to argue with.

It works in business, too. Most owners know exactly which tasks fall into the glad I did it column. The follow up with the prospect who went quiet. Updating the numbers so you actually know where you stand. Recording the process so somebody else can do it. Nobody enjoys those. Everybody's relieved once they're done.

Put them first. Let the fun stuff be the reward, not the warm up.

If you want to make this practical, try a short list. Write down five things that reliably land in your glad I did it column. Mine look something like a morning walk with Sheldon before the phone comes on, an hour of real writing, one honest outreach message, a workout, and ten minutes looking at the actual numbers in the business. None of them are glamorous. Every one of them makes the rest of the day better.

Then write down the three things that most often eat time without paying it back. Be honest. For most of us it's some mix of feeds, news, and email checking that pretends to be work.

You don't have to delete the second list. You just have to stop letting it go first. Fun isn't the enemy. It's just a terrible manager.

The second thing from that same episode was a section on intrinsic values. Things you care about for their own sake, not because they get you something else.

That sounds abstract, so here's how it landed for me.

I have a lot of goals right now. Business goals, fitness goals, writing goals, the whole stack. So I started asking one question about each of them. If nobody ever knew I'd done this, would I still want it?

Some goals passed easily. I want to be in shape because I like how I feel and I want to be around for a long time. Nobody needs to see that. I want to write well because I love the work itself, even on days nobody reads it.

Some goals got quiet when I asked the question.

There are a few numbers I've been chasing that I'm not sure I want for their own sake at all. I want them because of what they'd say about me. Because they'd prove something. Because they'd look good on a scoreboard I'm keeping for an audience that probably isn't even watching.

That's the difference. A compass goal points you toward something you'd want regardless. A scoreboard goal is about being seen getting there.

Scoreboard goals aren't evil. Sometimes a number is a useful way to measure progress toward something you actually value. But when the scoreboard becomes the whole point, two things happen. You hit the number and feel strangely empty, because there was nothing underneath it. Or you miss the number and feel like a failure, even if the thing you actually cared about was going fine.

ClearerThinking has a free intrinsic values test on their site if you want to go deeper. It's on my list for this week. In the meantime, here's the quick version you can do on the back of a napkin.

Write down your three biggest goals for the rest of this year. Next to each one, answer one question honestly. If I got this and couldn't tell a single person, would I still want it?

Keep the yeses. Look hard at the noes. Some of them might need to be rewritten. Some might need to be let go. A few might just need a better reason underneath them.

Here's what a rewrite can look like. Say one of your goals is to hit a certain follower count by December. Ask the question and the honest answer might be no, you don't care about followers for their own sake. But underneath it there might be something you do care about. Maybe it's having a real conversation every week with someone who needs what you know. Maybe it's building something your kids could be proud of. Write that down instead, and then ask what number would actually tell you you're getting closer to it. Sometimes it's the same number. Often it isn't.

I'm not saying ditch the ambition. Just make sure it's aimed at something you'll still want when you get there.

This one came from a few different places at once, which is usually how I know it's real.

Adam Grant's new book, the one I wrote about on Friday, pushes back on the idea that closeness requires a lot of time. That you can't really be close to someone unless you see them all the time.

Then I read the research piece in Friday's roundup about loneliness at work. The finding that stuck was that general invitations, the team happy hour in the group chat, don't reach the most isolated people. The personal invite does.

And then I looked at my own relationships and realized I'd been doing it backwards.

My instinct with people I care about is to save up for something big. A long dinner. A weekend visit. A real catch up call when we both have an hour. Those are great when they happen. The problem is they don't happen very often, because life is busy and an hour is a lot to find. So in between, there's nothing. Weeks of nothing. And then the big thing feels a little stiff, because we're catching up on a month instead of continuing a conversation.

What actually seems to keep people close is smaller and more frequent. A thirty second text that says "saw this and thought of you." A voice memo on a walk. Remembering the thing they were nervous about last week and asking how it went.

None of that takes an hour. It just tells them you're paying attention.

So I'm flipping it. Instead of waiting for the hour, I'm sending the small, specific check in to the people I keep meaning to call "when I have time." It costs almost nothing. And it keeps the thread alive, so when the long dinner does happen, we're picking up a conversation instead of starting one from scratch.

If you're wondering what that looks like in practice, here's the short menu I'm working from. None of it takes more than two minutes.

Send a photo of something that reminded you of them, with one sentence about why.

Ask a follow up on something they told you last time. "How did the meeting with your landlord go?" beats "how've you been?" every single time.

Leave a voice memo instead of a text. Hearing someone's actual voice does something a text can't.

Pass along an introduction or an article that's useful to them specifically, not to everyone.

And when something good happens to them, say so. Out loud. Most people's wins go by without a single person noticing.

The lesson I'm taking into next week is simple. Stop saving connection for when you have time. Spend it in small amounts, often, and make every one specific enough that it couldn't have been sent to anybody else.

The same thing goes for anyone who leads a team, runs a group, or hosts anything. The group invite is easy and it misses the people who need it most. The personal one takes thirty extra seconds and reaches them. Send the personal one.

Nothing earth shattering this week. Just a better filter for my mornings, a harder look at a few goals, and a reminder that the people I care about don't need an hour from me. They need me to show up more than once a quarter.

Here's the small version for this week. Pick one person you've been meaning to "really catch up with" for months. Don't schedule the big call. Send them something small and specific today, and let the conversation start where it starts.

If that sounds too simple, good. Most of what actually works is. The hard part was never knowing what to do. It's doing it on a Tuesday when nobody's watching and nothing's on fire.

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