I’m a professional repeater.
Ask me why I left rocket science to go to law school, and I have an answer for that. Why I gave up tenure. How I decided to write books. What the hardest part was.
After enough stages and enough podcasts, there isn’t a question I haven’t been asked, and every answer has hardened into a script—sanded down, timed, with a pause before the line that always gets the laugh.
The scripts work. And that’s the whole problem. The rehearsed answer is dead the moment it leaves my mouth.
At a dinner recently, someone asked me So what do you do?, and somewhere in the second sentence of my answer, I noticed I wasn’t there. The mouth kept going. The beats landed where they always land. And I stood off to the side of my own body waiting politely for it to finish.
What struck me wasn’t that I was boring them. I was boring myself. There was no room in that answer for anything to happen. No surprise, no wrong turn, nowhere for the conversation to go that it hadn’t already gone. It was a performance of a conversation. All score, no jazz.
I’m sure you’ve felt some version of this. Tell the story of a trip enough times and the story eats the trip. The retellings wear a groove where the memory used to be. You go looking for the afternoon in Lisbon and you find the story about the afternoon in Lisbon—smooth, rehearsed, and somehow no longer the thing that actually happened.
Here’s what makes it so seductive: The rehearsed answer is genuinely good. It’s polished, it lands, it makes you look smart.
But you lose the thing that’s actually alive. The unformed thought. The thread you don’t know the end of. The conversation that could only have happened this once, with this person, in this room.
Saying the unformed thing means tolerating not knowing where it’s going. You open your mouth into open space with no landing built, and you have to let the sentence construct its own runway on the way down. And every so often it lands somewhere you’ve never been and you get surprised by your own mouth.
Now, when I notice myself reaching for a polished answer, I try to pause and share the unformed one instead.
Sometimes I say Let me think about that out loud, which lets me stay open for a half-second longer and gives the live answer a chance to show up. It also tells the other person the polished version isn’t coming, that what follows might wander, and that they’re welcome to interrupt it. People often relax when they hear it.
Sometimes I change the question. Onstage once, someone asked what advice I’d give my 17-year-old self—a question I’d answered many times before. I said, The more interesting version is the reverse: what advice would that 17-year-old give me?
And with a question like What do you do?, I’ve made it a game not to answer the same way twice. Some days I’m a storyteller. Some days I’m a rocket artist. Some days I’m a professional quitter.
Half of these go nowhere. But every so often one opens sideways, and we end up somewhere neither of us planned.
The polished answer is something I already know.
The unfinished one is how I find out what else is in me.
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