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On Optimizing Yourself Into a Corner

A better way to think about flourishing and leadership

"I don't want to do this anymore."

A friend told me that recently. The thing he doesn't want to do anymore is the thing he spent twenty years building. The company works, the family is intact, the reputation is real. He wasn't being dramatic when he said it. He said it the way you'd read a lab result.

I couldn't make his life add up to his sentence. Then I stopped looking at his life and looked at his Tuesday.

By nine he has answered a board member, signed a school form, put out a hiring fire, skimmed a feed full of strangers' opinions, and left a friend's text sitting unanswered for the fourth day, the one he keeps meaning to answer well and therefore doesn't answer at all. That's five worlds and it isn't nine a.m. By dinner he'll have visited a dozen. None of them touch. The board member doesn't know his kid's name. The school doesn't care about the board. The feed doesn't know him at all. Every world wants more of him than it gets, so he ends each day owing something to someone, and starts the next one behind.

Ask how he's doing and he says busy, which is true and tells you nothing. Nothing gets enough of him to be satisfied. Not the company, the family, the friend, or him. He is failing every sphere by a little while being told from every direction that he's killing it.

The fixes

He didn't get there by neglect. The volume went up, and our answer was optimization.

We optimized the day first. Time blocking, inbox zero, the calendar audit, and when the systems weren't enough, the guilt genre: no email in bed, no email at dinner, no email in the meeting about email. We read those books. We bought them for our teams, which is what you do with a book that's about you. Some of it helped. But the tighter the schedule got, the more worlds fit inside it.

We optimized what we take in. The feed learned what holds us, and the answer began arriving before the question had finished forming. Curiosity used to cost a walk, a conversation, a book you had to find. Now we can be interested in everything for about eleven seconds. Because it feels like learning, we barely notice how rarely it adds up to knowing.

We optimized relationships too. Network wider. Treat each connection as an investment. Prune the ones that don't return. That misunderstands what relationships are for. The ones that give us security and honesty are usually the ones Lewis called unnecessary, the ones that return nothing you could enter in a ledger. A circle also does something a portfolio cannot: every time it gathers, several bonds grow stronger.

The logical end of optimizing people is removing them. The humans are the friction; the model doesn't complain or quit or need context twice. We spent a century trying to optimize people out of work. The tools finally got good enough to aim the old premise at ourselves: the company of one, building everything alone with a mirror that charges by the token.

Line up the calendar, the feed, and the network. Each assumes the broken unit is you, alone, and the repair is you, alone: the day into slices, the mind into feeds, the people into transactions.

Our answer to the volume was optimization. Optimization is how we got divided.

What the fixes can't touch

The fixes were aimed at capacity, and capacity was never the shortage. You can execute a perfectly engineered week and reach Friday unable to say what it was for.

A farmer three hundred years ago spent every drop of attention he had, same as us. But the weather decided the crop, the crop fed the family, and the family belonged to a place he would die in. His life was hard in ways we've forgotten, but one thing bore on the next. He was one man in one world.

My friend is a dozen men in a dozen worlds, and not one of them is the room he's standing in. So are most of us, give or take a world.

Not overloaded. Divided. And stay divided long enough and it reaches who you take yourself to be: you can perform in every world and be known in none of them.

This is not a new problem

Three thousand years ago, a man with a king's resources ran the experiment. Solomon tried every pleasure, project, and kind of mastery available to him. The word he kept returning to gets translated from Hebrew as vanity, though it sits closer to vapor. He wasn't preaching. He was reporting.

We keep running the same experiment with better tools.

The way back

Three disciplines help with the slow work of getting undivided.

Attention comes first, because that's where the dividing starts.

For most of human history, what we could attend to was mostly what was near. Reaching farther took effort. Now the phone can keep us alarmed all day about things we cannot touch. Some walls help, but attention is more than walling the world out. It is choosing what deserves you and turning toward it. For leaders, that choice spreads; people learn what matters by watching what gets their attention.

Curiosity is second, and it dies in a way most people miss, because what kills it feels like competence.

Constructive curiosity holds two things together: I don't know, and I can learn. Success can turn the second into "I already know," which feels almost identical from the inside. Confidence feels the same whether you're seeing clearly or living inside a distorted picture of reality. Someone else has to check your vision.

Curiosity also needs security. It is hard to explore when your worth is on the line every time you're wrong. Pressure doesn't make people less intelligent. It makes them less curious.

Friendship is third, and it's the one optimization can't survive.

We drift toward wide, shallow networks because deep friendship asks more of us. Stay long enough and the impressive version disappears. Your friend becomes the person who talks too much or still forgets your kids' names after meeting them a dozen times. Quick vulnerability can create the feeling of being known without the years in which someone actually knows you, including the unimpressive version.

What you want is small and hard to fake: a handful of people who run alongside you for decades, who need nothing from you, who would think the same of you if the whole thing folded tomorrow. That is where curiosity gets its security, because your worth is no longer riding on the answer. Lewis put friendship among the things that have no survival value, like philosophy and art, and then said they are what make survival worth having.

Whatever the good life turns out to be, you're not going to get there alone.

Curt speaks about this. → Keynotes