From Certainty to Curiosity

20 years ago I turned 19 and thought I had the world figured out. I was certain I knew how to lead people, certain I knew myself, certain there was nothing more to learn. Never mind that I had never led anyone, spent zero time exploring who I was, or had only scratched the surface of most topics. My certainty was my armor.

Today I turn 39, and I am less certain than ever. I have built companies, led teams, invested in startups, and done more self-work than my 19-year-old self could have imagined. Yet with each passing year, it becomes clearer how much I don’t know. And surprisingly, this uncertainty brings more comfort than certainty ever did.

I found freedom when I stopped pretending to have all the answers. Freedom to ask "stupid" questions. Freedom to change my mind. Freedom to learn from anyone, regardless of their title or experience.

Take leadership, for example. At 19, it seemed simple: tell people what to do, they do it, success follows. How hard could it be?

Twenty years and countless mistakes later, I've learned that leadership isn't that simple. Every person brings their own universe of experiences, fears, and ambitions. Just when I think I've mastered communicating with someone, I meet others who process information in completely different ways.

What's helped me most is accepting that I'll never master this. Instead of trying to be the expert, I focus on being present. I shut up and listen to what people are telling me, through both their words and their silences.

This approach mirrors what Zen Buddhists call “beginner's mind” - approaching each situation as if we know nothing about it, regardless of our past experience. This mindset transforms every interaction into an opportunity to learn something new, to be surprised, to grow.

In meetings, I'm often the one who raises their hand to say “I don't quite understand - could you explain it differently?” When leaders come to me for coaching, I start with “I'm not sure what the best approach is. What do you think?” Leading with curiosity makes people feel seen and heard, brings their whole selves forward, and surfaces ideas that might otherwise stay hidden.

These moments of curiosity create space for genuine exploration. Each time I choose uncertainty over false certainty, I rediscover that sense of freedom that comes from letting go.

Looking back at my 19-year-old self, I can see how that certainty was actually a cage of my own making. Now, at 39, I find comfort in approaching each day with a beginner's mind, knowing every interaction holds the possibility of surprise.

And you know what? I can't wait to turn 59! Not because I'll have more answers then, but because I'll have discovered even more beautiful questions to ask. Because true wisdom, I've learned, isn't about accumulating certainty. It's about maintaining the courage to stay curious.