
"I Don't Know" Changed Everything
Feb 15, 2026
We had @DannPetty on the podcast this week.
If you don't know Dann, he's designed for Google, Airbnb, Nike, Activision. Created Epicurrence. Been freelancing for over twenty years. So he has done a lot.
With all that, there were three words that made the most impact.
Early in his career, Dann was working on what would become Medium. Tiny team with a massive ambition. And leading the whole thing was Ev Williams, the co-founder of Twitter (!!) creator of Blogger. One of the people who literally shaped how we use the internet.
Dann kept going to Ev when he was stuck. Looking for direction. Hoping the guy with the biggest stamp in the room would just... tell him what to do.
And every time, Ev said the same thing:
"I don't know. Let's go figure it out."
He'd skip meetings. Go for walks. Just sit in the problem with Dann instead of pretending he had it solved.
And that wrecked Dann in the best way possible.
Because everyone else around him was doing the exact opposite. Posturing. Performing. Trying to be the smartest person in the room. You know the energy. You've been in those rooms.
And here's the guy who actually built the things… just being honest about what he didn't know.
Let that sit for a min now.
Because I've been the other guy. The one ove -explaining a design direction I wasn't even sure about. Adding more words because silence felt like I was losing the room. Talking past the point instead of just saying, "I'm not sure yet. Give me a minute."
We've all done it.
And then every once in a while, you're in a room where someone senior just goes, "Yeah, I don't know." And everything relaxes. It stops being a presentation and starts being a conversation.
There's a version of confidence that looks like having all the answers thats fast, loud and certain.
And there's another version that sounds more like, "I don't know, but I'll figure it out with you."
That second one is rarer and it builds more trust than any polished rationale ever could.
Dann said something else I keep thinking about and it's the fact that the people who can admit they don't know and are genuinely willing to sit in it with you? Those are the ones you want to work with. And there aren't many of them.
He's right. "I don't know" feels like you're giving something up. Like you're exposing yourself.
But you're not. You're just making room for something better than a performance.
I still catch myself reaching for the impressive answer instead of the honest one. Probably always will.
But the best work I've ever been part of didn't start with someone having it figured out.
It started with someone being okay with not having it figured out.
And saying so out loud.