The Power of Wonder: Why "I Don't Know" is Your Greatest Leadership Asset
"Can you just notice that you're scared and feel the sensations in your body?" I asked my client during our morning call.
He'd been spiraling for the past ten minutes about his Series B fundraise.
The data room had been live for less than twelve hours, only two investors had accessed it so far, and his mind was already catastrophizing: Maybe I need to talk to my team about what happens if we don't raise money. Maybe I should pivot the strategy. Maybe...
"There's this knot in my stomach," he said, his voice tight. "Like everything's closing in."
"Good. Just be with that for a moment."
I could hear him breathing on the other end of the line.
"You know what's interesting?" I said. "You're trying to solve a problem that doesn't exist yet. The fundraise isn't failing – you just don't know how it's going to unfold."
The shift in his energy was immediate. His breathing deepened. The frantic edge in his voice softened.
"That's... relieving," he said, sounding surprised. "I've been treating this uncertainty like the worst is guaranteed to happen when I actually have no idea."
"Exactly. The fear doesn't come from the uncertainty itself. It comes from your imagination of what could go wrong. You could meet that same uncertainty with wonder instead.”
That conversation revealed the power of wonder – one of the most powerful advantages that leaders throw away every day.
Once you see how uncertainty actually serves you, opportunities will show up everywhere.
Why We Struggle With Uncertainty
Here's the foundational insight:
When you know, you are relating to the current situation from the past.
When you are in the past, you are not in reality. You are in the mind experiencing memory, which no longer exists here in reality.
So the bridge outside of the mind into the present moment, where everything is real, alive, and true... is curiosity.
Or in other words, saying the words "I don't know" and seeing everything for the first time with all its novelty.
But here's what's happened: If we're really honest with ourselves, most of us have atrophied our childlike wonder, our sense of curiosity. We're generally much more oriented toward convergence than divergence – we want to know the right answer and get to it as quickly as possible.
I see this constantly with the founders I coach. They've trained themselves to:
- Always have a plan (even when the situation calls for exploration)
- Appear confident (even when uncertainty would serve them better)
- Solve problems quickly (even when the problem isn't fully understood yet)
- Know their numbers (but ignore their intuition and emotional intelligence)
This is why my client wasn't stuck because he lacked information. He was stuck because he was living in an imagined future based on past patterns. The moment he said "I don't know" and got present, everything shifted.
The Two Ways We Meet Uncertainty
If you really look, there are two primary ways that we humans meet uncertainty: fear and wonder.
And it's the same uncertainty.
Picture this: You're about to walk into a crucial investor meeting. Your mind can go one of two directions:
Fear response: "Oh god, I don't know how this meeting is going to go. What if they ask about our burn rate? What if they've already decided no? I'm not prepared enough."
Wonder response: "I wonder what's going to come out of this conversation. I wonder what insights they'll share. I wonder how our visions might align in ways I haven't imagined yet."
Same meeting. Same uncertainty. Completely different energy in your system.
From my experience, fear and wonder can't coexist. When you choose wonder, you literally can't be afraid at the same time. Whereas fear makes you myopic and stressed, curiosity is enlivening and expansive.
The "I Don't Know" Leadership Framework
Here's how to practice this transformation:
1. Welcome "I Don't Know"
When you feel that familiar anxiety of not knowing what to do, pause and say, "I'm actually confused about this, and that's okay."
Start saying "I don't know" in meetings, with your team, with investors. Follow it immediately with: "Let's figure it out together" or "What do you think?"
Most leaders fight confusion because they think it's a problem to solve. But confusion often signals that you're on the edge of a breakthrough – you're integrating new information that doesn't fit your old mental models.
2. Choose Wonder Over Fear
The next time you catch yourself spiraling with worry, interrupt the pattern with wonder questions:
- "I wonder what this situation is here to teach me?"
- "What would we do if we started all over?"
- "What's one thing we've never tried that just might work?"
Treat these questions as doorways into new possibilities rather than quizzes where you need to get the answer right. Fear and wonder can't coexist – when you choose curiosity, you literally can't be afraid at the same time.
3. Trust the Present Moment
Wonder requires trust – trust in life, in your team, and in yourself.
When you stop trying to control outcomes and start getting curious about what wants to emerge, you often discover solutions that are far better than anything you could have planned.
Remember: you're not living in the past (what you know) or the future (what you fear) – you're creating from the present moment where everything is alive and possible.
The Uncertainty Paradox
Here's something fascinating I share with every founder I work with: We both crave certainty and uncertainty.
Think about it – if you knew exactly how your startup journey was going to unfold, it would be like watching a movie you'd already seen. Boring.
That's partly why we do this entrepreneurial work: because it's our edge, it's risky, it's the excitement of stepping into the unknown and creating something new. The uncertainty isn't a bug – it's a feature.
But then sometimes we're like, "This is so scary! It's so uncertain!"
So I invite you to choose wonder. Let yourself be excited by the mystery rather than threatened by it.
The Transformation
Remember my client with the stalled Series B? Within 48 hours of our call, he stopped trying to figure everything out and instead got curious about what his investors were actually looking for. He reached out with genuine questions rather than desperate pitches.
Two weeks later, he had three term sheets.
"I realized I was so busy trying to have all the answers that I forgot to ask the right questions," he told me. "As soon as I admitted I didn't know everything, everyone started wanting to help me figure it out."
When you lead with curiosity instead of false certainty, you:
- Build stronger relationships
- Resolve conflicts with ease
- Make better decisions
- Inspire your team to think bigger
Because great leadership doesn’t look like knowing all the answers. It's asking the right questions.
The next time you feel that familiar anxiety of uncertainty, try this: take a deep breath and say, "I don't know... and I wonder what's possible here."
You might be surprised by what emerges.
With love,
