Sunday, October 11th, 2026

Quick note before we start. If you read yesterday's letter, you know I didn't run the race. I'm not going to rehash it. The short version is that I made the call, I'm at peace with it, and the training still counted.

What surprised me is how much I learned from the week anyway. Getting ready for something strips your days down. You sleep more, you schedule less, and you notice what's actually eating your energy because you can't afford to waste any of it. That stayed true even after the plan changed. All three of these changed something about how I'm working, which is the only test I care about for this letter.

I've been reading The Courage to Be Disliked all week, and the idea from it that's been most useful by a mile is the least poetic one in the book.

The philosopher calls it the separation of tasks. When something's bothering you, you ask one question. Whose task is this? And the way you figure that out is to ask who ultimately lives with the result of the choice.

That's it. It sounds too simple to matter. It isn't.

I started running it on everything that made my chest tighten this week, and the results were embarrassing in a useful way.

A prospect went quiet after a call that I thought went well. My old reflex is to start drafting the follow up in my head. The light one, the funny one, the "just checking in" one, the one that gently reminds them what they're missing. Then I'd spend an hour wondering what I said wrong.

Whose task is that? My task was to run a good call, give them a clear next step, and follow up once like a professional. I did that. Whether they decide to move forward is their task. They're the one who lives with that decision. Me worrying about it doesn't change it. It just costs me an afternoon.

Somebody I respect had an opinion about the way I'm rebuilding. Not a mean one. Just a raised eyebrow. And I felt that old urge to explain. To send a long message laying out my reasoning so they'd understand and approve.

Whose task is their opinion? Theirs. My task is to make good decisions and own them. Whether somebody else is comfortable with those decisions isn't mine to manage.

Here's the practical version I've been using. When something lands in my inbox or my head that I feel a strong urge to react to, I write three quick lines.

What's mine here?

What's theirs?

What's shared?

Then I only act on the first line and the third. The second one I set down.

There's a catch, and the book is clear about it. This isn't permission to stop caring about people. You can still help. You can still offer. You just can't do their task for them, and you definitely can't make yourself responsible for how they feel about the way you did yours.

What surprised me most is how much of my stress lived in the middle column. Probably more than half. All that energy, spent on things I had zero ability to change.

I cut three long emails down to two sentences this week because I realized most of what I was writing was an attempt to manage how somebody would feel when they read it. The short versions were clearer. Nobody was offended. And I got my evening back.

This works in business in a way that's almost unfair. Think about how many hours a month you spend on things in the middle column. Rewriting a proposal because you're worried what the prospect will think of the price. Softening feedback to an employee so much that the feedback disappears. Checking whether a client opened your email. Lying awake wondering if somebody's annoyed with you.

All of that is effort aimed at a target you can't hit. You're trying to do somebody else's task from the outside, and they don't even know you're doing it.

Pricing is the clearest example. Your task is to price your work honestly and explain it clearly. Whether the buyer thinks it's worth it is their task. When owners get those two confused, they start discounting before anyone's even asked.

I listened to Sam Sulek on Modern Wisdom this week, the episode about going hard when you don't want to. And the thing that stuck wasn't anything dramatic. It was how boring his approach is. Show up, do the basics, do them with intensity, do it again tomorrow.

It made me look at how I set goals for myself, and I didn't love what I saw.

I set ceilings. The ideal version of the day. Five mile run, two hours of deep work, ten outreach messages, a long journal entry, the whole thing. On good days I hit most of it and feel great.

On bad days I look at the ceiling, realize I'm not going to get anywhere near it, and do nothing. If I can't do the real version, why bother with any of it?

That's an all or nothing trap, and it's been quietly running my life for a long time. The good days were great. The bad days were zero. And it turns out the bad days are where habits actually live or die.

So this week I set floors instead.

The floor is the smallest version of each thing that still counts. Not the ideal. The minimum I'd be proud to say I did on my worst day.

For running, the floor is fifteen minutes in my shoes outside. Any pace. No race required. That one matters more to me this week than it did last week, because the floor is what keeps a cancelled race from turning into a cancelled habit.

For deep work, the floor is one paragraph of the hard thing. Not the whole thing. One paragraph.

For outreach, the floor is one real message to one real person.

On the days I don't want to do anything, I don't negotiate with the ceiling anymore. I just hit the floor. And here's the part I didn't expect. About half the time, once I'm at the floor, I keep going. Fifteen minutes turns into thirty. One paragraph turns into a page. The hardest part of the whole thing was starting, and the floor made starting cheap.

The other half of the time I just hit the floor and stop. And that's fine too, because the streak isn't the point. The identity is. I'm someone who runs. I'm someone who does the hard work first. The floor protects that on the days the ceiling would have broken it.

If you've got a habit that keeps dying on bad days, the problem probably isn't discipline. It's that the only version you've given yourself is the one that requires a good day.

Set the floor low enough that you'll hit it sick, tired, annoyed, and behind. Then hit it. Every day.

The same idea works for the business, by the way. Most owners have a ceiling version of every important habit. The full weekly pipeline review. The perfectly written newsletter. The hour of prospecting. When the week gets ugly, the ceiling becomes impossible, so the whole habit disappears for a month.

Give each one a floor. The pipeline floor might be looking at your top five deals for ten minutes. The content floor might be one honest paragraph. The prospecting floor might be one conversation. Small enough to survive a bad week. Real enough to keep the muscle from going soft.

This one's going to sound backwards, so let me explain.

There's a section of the book where the philosopher argues against praise. Not criticism. Praise. And the young man in the book, like me, thinks this is insane. Praise is good, right? Encouraging people is good.

The philosopher's point is that praise comes from above. When you tell somebody "good job," you're grading them. You're the judge, they're the one being judged, and the relationship is vertical. It's the way an adult talks to a kid. Even when it's warm, it carries a quiet message: I'm in a position to evaluate you.

And people who grow up on praise, he argues, start living for it. They do things to be graded well instead of because the thing is worth doing. Which, if you've ever managed people, you've seen. Somebody who does great work while you're watching and coasts when you aren't.

His alternative is gratitude. Not "good job." "Thank you, that helped me." It sounds like a small swap. It isn't.

"Good job" says: I evaluated your work and it passed.

"Thank you, that helped me" says: what you did mattered to me. It's two people standing on the same level.

I tried it this week with everybody I work with, and it felt awkward for about a day. Then it felt better than praise ever did, on both sides.

The trick is being specific. Not just "thanks." What did they do, and what did it change for you? "Thanks for catching that error before the client saw it, that saved me a really bad afternoon." No grade in there anywhere. Just a fact about how their work landed in your life.

And there's a mirror version of this that's harder.

I've noticed how often I fish for praise myself. The little "did you see the thing I did" moments. The posts I check too many times. The emails where I mention a win just a little too casually. That's me asking to be graded. It's me handing somebody else the job of deciding whether I'm doing well.

That's not their task. It's mine.

If you lead a team, this one is worth a real experiment. For the next two weeks, every time you're about to say "great job" or "nice work," swap it for a specific thank you. Watch what happens to the conversations. My guess is people start telling you more about what they're working on, because they're not waiting to be graded anymore. They're just sharing what they did with somebody who noticed.

So the lesson cuts both ways. Thank people instead of grading them. And stop asking to be graded yourself.

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That's the week.

Three versions of the same idea, if I'm honest. Stop carrying what isn't yours. Lower the bar so you'll actually clear it. And stand next to people instead of above them, or below them.

Here's the small version for this week. Next time somebody does something that helps you, don't say "good job." Say "thank you, that helped me," and tell them how. See what happens to their face.

And if you had something fall through this week, a launch, a deal, a race, a plan, I hope you'll give yourself the same deal I'm giving myself. The work still counted. Pick up the floor on Monday and keep going.

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