Choosing Curiosity Over Certainty: A Mindset for the Modern Age
I tend to think of my life in two distinct periods: the first, when I didn’t know anything. And the second, when I realized I didn’t know anything.
That shift—from unknowing to knowing I didn’t know—changed everything for me. Not overnight, but over time. It transformed how I approach learning, how I run a business, how I have conversations, and how I show up in the world.
In that first period, I was full of confidence in my beliefs. Whether it was politics, philosophy, spirituality, or whatever big idea was on the table—I had an opinion, and I held it tightly. If you disagreed, well, then it was time to debate. And I didn’t enter debates to exchange ideas. I entered them to win.
That need to be right? It didn’t come from malice. It came from a place I thought was noble: conviction. Passion. Purpose. But the older I got, the more I started to realize that certainty, especially in excess, is a form of blindness.
When the Cracks Started to Show
Somewhere in my late twenties, things started to shift.
I couldn’t help but notice how often I was wrong. How frequently new information came in that challenged the views I’d held tightly. I’d read something, hear a new perspective, or live through a situation that forced me to re-evaluate what I thought I knew.
And each time I changed my mind, I didn’t shrink. I grew.
The more I embraced that, the more liberating it became. I stopped needing to win arguments. I stopped needing to plant a flag on every topic. And I started getting curious. Not curious in a performative way, but deeply, sincerely curious about what I didn’t yet understand.
That was the beginning of the second period of my life: the one where I realized just how much I don’t know—and how powerful that realization really is.
A Lesson from the Startup Trenches
That mindset got put to the test when I built my first company. If there’s ever a crash course in letting go of ego, it’s entrepreneurship.
You go into a startup with ideas—strong ones. Beliefs about what customers want, how the product should look, what pricing should be, how to market. But the market doesn’t care how right you think you are. It only cares about what actually works.
That’s when I discovered a powerful mental framework: strong convictions, loosely held.
It means believing passionately, but not rigidly. Testing boldly, but adapting quickly. Holding your ideas like clay, not concrete.
This mindset saved me—more than once. It helped me pivot when a product wasn’t working, listen more closely to customers, and evolve faster than I ever could have if I’d stayed locked into “being right.”
The Joy of Not Knowing
Something else happened, too. As I became more curious and less certain, I started having better conversations.
Instead of listening just to find an opening for my rebuttal, I started listening to understand. Instead of needing to prove a point, I asked more questions. And guess what? I learned more. Not just facts, but about people. About where they come from. What they’ve lived through. Why they believe what they believe.
And I think—I hope—I became more enjoyable to be around.
Because let’s be honest: nobody likes talking to someone who always needs to be right. It’s exhausting. But talking to someone who’s open, who’s learning in real-time, who’s curious? That’s energizing.
Curiosity makes you lighter. Certainty is heavy.
Why This Mindset Matters (Now More Than Ever)
We live in an age where certainty has become a kind of performance art. Social media rewards the boldest take, the strongest stance, the snappiest takedown. Nuance? Not so much.
But here’s what I’ve found: choosing curiosity over certainty has made me not only happier, but more effective. In business. In relationships. In life.
Here’s why:
- You learn faster. When you’re not defending old ideas, you’re open to better ones.
- You connect more deeply. People feel safe with someone who’s listening, not judging.
- You become more creative. Certainty narrows options. Curiosity expands them.
- You find more peace. There’s no internal tension when you don’t need to be right all the time.
As the Stoics would say, we suffer more in imagination than in reality. And much of that suffering comes from our belief that we’re supposed to know everything. That’s a trap. And it's one you can step out of at any time.
Practicing Curiosity Daily
So how do you start? Here are a few things that help me:
- Adopt the mantra: “I could be wrong.” Say it often. It softens your grip on certainty.
- Ask more questions than you make statements. Especially when someone disagrees with you.
- Listen to understand, not to reply.
- Don’t tie your identity to your ideas. You’re allowed to evolve.
- Consume content that challenges you. Not to argue with it, but to learn from it.
- Celebrate mind-changing moments. They’re signs of growth, not weakness.
The Freedom in Uncertainty
At this point in my life, I don’t want to be the guy with all the answers. I want to be the guy who asks good questions. Who learns out loud. Who changes his mind in public and is better for it.
Because the truth is: I don’t know. And neither do you. Not fully. Not forever. That’s what makes life interesting.
So if you’re stuck in a mindset of always needing to be right, try loosening your grip. You might just find, like I did, that there’s a whole world waiting on the other side of certainty—full of wonder, wisdom, and the quiet joy of not knowing.









