optimize

May 6, 2026

Why I shaved my head

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A note on speaking before we get into it: I’m doing fewer keynotes this year on purpose. Only four spots are still open for the rest of 2026. If you’d like me at one of your events, details here.

On to the regularly scheduled programming.


I shaved my head last month.

My hair had been thinning for a while. I’d looked into the alternatives: transplant, pills, the whole industry built to keep you exactly as you were.

But each option felt like performing CPR on something that was clearly dying.

So I picked up the clippers.

The next morning, I looked in the mirror and didn’t recognize the man looking back. A little jolt. A flicker of Who is that?

And then—relief.

I’d been managing my hair for years. Adjusting the part. Holding a small, constant negotiation in the back of my mind every time I caught my reflection (What do I do with this?). I hadn’t realized how exhausting it was until it stopped.

Most things in life don’t end. They thin.

Hair thins. Friendships thin. Careers thin. Identities thin. Audiences, beliefs, the version of yourself you used to be proud of—they rarely break. They fade.

Some things that fade are worth fighting for. But some things are just dying.

And we treat it like a problem to solve. We Google. We supplement. We optimize. We learn the language—”Now isn’t the right time,” “I’ll come back to it,” “It’s not too bad.”

What we’re really saying is: I don’t want this to be over, so I’m going to keep performing that it isn’t.

That was me with my hair for years.

In the past, I would say, “I can make this work.”

But then I started to ask, “Do I even want to?”

I used to say, “I’m losing this.”

Now I say, “I’m putting the blade to it myself.”

The “losing” language puts you in the passive seat—something is being taken from you, so you naturally brace and protect.

I didn’t shave my head because I was rejecting loss. I shaved it because I wanted to be the one who decided when this chapter was over.

Someone else might make a different call and get the transplant or try the pills. That can be its own kind of agency—choosing to keep something because you actually want it, not because you’re afraid of what’s underneath.

For me, shaving was a declaration: Bridges aren’t meant to be lived on. They’re meant to be crossed.

The job you finished caring about months ago but still show up to with the right facial expressions. The friendship you keep on low heat because cooling it down feels too final. The conversation you’ve mentally exited but haven’t physically left. The version of yourself you outgrew years ago and still perform when the right people are in the room.

Hold that posture long enough and you forget what aliveness even feels like.

The things that are dying in your life aren’t asking you to save them. They aren’t asking you to optimize them past their natural life.

They’re asking you to let them go and step forward into whatever comes next.

Most things deserve to be ended on purpose, before they decay into something you don’t even recognize.

Because the alternative isn’t keeping it alive.

The alternative is just a longer goodbye.

Bold