Letting Go of the Need to Be the Smartest in the Room

Somewhere along the line, we were taught that leadership meant having all the answers. To be taken seriously, you had to speak with authority, never show doubt, and definitely never say, “I don’t know.”

But here’s what I’ve learned after years of building things—from newspapers to music festivals to film careers: pretending to be the smartest person in the room is often the fastest way to stop learning.

The most powerful moments in my career didn’t come from my brilliance, they came from my willingness to ask dumb questions, to listen harder than I talked, and to be okay with not knowing.

That’s what I mean by being stupid: not ignorant, but open. Not arrogant, but honest.

“Stupid” Opens Doors Ego Slams Shut

The truth is, ego is a door closer. It walks into a room and blocks out possibility.

But the minute you let go of needing to impress people, when you stop trying to be the hero and start being a collaborator, real connection happens. Ideas flow. Walls come down. People show up with their full, messy brilliance.

I’ve had interns say something that changed an entire project’s direction, volunteers make calls no one else had the guts to, and unexpected voices speak the truth we didn’t want to hear, but desperately needed to.

If I’d been too full of myself to listen, we’d have missed all of that.

Being “stupid” enough to listen, to really listen has served me better than any resumé ever could.

Honesty Is a Creative Superpower

People love to talk about creativity as this sparkly, mystical thing. And yes, there’s magic in it, but there’s also something very raw and grounded about it, too.

The best creative work doesn’t come from ego. It comes from honesty. From being brave enough to say, “This isn’t working.” Or, “I have no idea where this is going, but let’s find out.”

Some of the best moments in SXSW’s history started with something uncertain, unpolished, or even kind of dumb-sounding. But when you give those imperfect ideas space, when you treat them with curiosity instead of judgment, sometimes they grow into something brilliant.

That only happens when ego isn’t choking the room.

People Can Feel When You’re Full of It

Let’s be real, people can feel when you’re performing leadership instead of practicing it.

They can tell when you’re protecting your image instead of participating in the work. They can sense when you’re bluffing your way through a conversation instead of asking the question you’re too proud to say out loud.

And the flip side is also true: they notice when you’re being real.

When you say, “I don’t know, but I’ll find out.”
When you admit a mistake before anyone points it out.
When you give credit away freely and take the blame with grace.

That kind of honesty is magnetic. It builds trust faster than any presentation or title ever could.

The Best Leaders Don’t Take Themselves Too Seriously

I’ve never trusted leaders who can’t laugh at themselves. If you’re too busy maintaining your image to laugh at a bad call or a ridiculous moment, how are you supposed to create a culture of risk-taking and growth?

I’ve made plenty of mistakes: loud ones, expensive ones, embarrassing ones. But I also never tried to pretend otherwise.

Self-deprecation, when it’s sincere, can be the most humanizing form of strength. It tells your team: I’m not above you. I’m in this with you.

And when people feel that, they don’t just follow you, they build with you.

Curiosity Over Certainty

There’s a temptation, especially in leadership, to chase certainty. We want clear answers, clean strategies, guaranteed results.

But what I’ve learned is that curiosity is far more powerful than certainty.

Certainty closes the loop. Curiosity keeps it open.
Certainty says, “I’ve got this.” Curiosity says, “Let’s see what we can learn.”

When I lead from curiosity, when I’m okay with not knowing, with being the person in the room asking the so-called dumb question, I give permission for everyone else to show up with their own questions.

And that’s when real breakthroughs happen.

Drop the Act, Do the Work

There’s something deeply liberating about giving up the performance of having it all together. About trading the appearance of control for the practice of presence.

Being stupid is not about lowering your standards, it’s about lowering your defenses.
It’s about trusting that your value doesn’t come from having all the answers, but from creating space for truth to emerge.

So here’s what I try to remember, especially when I’m tempted to armor up and act like I’ve got it all figured out:

• Stay curious.
  
• Admit what you don’t know.
  
• Laugh at your mistakes.
  
• Give other people room to shine.
  

And above all: Be stupid. Stay honest.

It just might be the smartest thing you ever do.