How Leaders Stay Grounded in Uncertainty

There’s a strange trend in business right now. We’ve started to idolize certainty. We hand out gold stars to the boldest plans, the loudest LinkedIn posts, the people who declare with full confidence that they know exactly what’s coming next.

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Everyone’s building frameworks. Spinning up five-step plans that promise clean progress and calm. There’s something comforting about it. But lately I’ve been asking myself, when did certainty become the prize?

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Because when I look back at the moments that shaped me most as a leader, none of them came wrapped in clean forecasts or tidy OKRs. They came as gut checks. Late-night realizations. Tense conversations I didn’t want to have. Uncharted turns I couldn’t logic my way through.

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And as uncomfortable as those moments were, they sharpened me. They woke me up.

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The Danger of Clinging to the Plan

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Certainty feels good. It makes you feel like you’re the smartest person in the room. That you’ve cracked the code that everyone else is still fumbling through. But here’s the thing about certainty. It’s a trap.

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It narrows your view. It tricks you into thinking you’ve arrived. That you don’t need to listen as closely. That you’ve already got it handled.

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And when you stop listening, you start missing. You miss the signals. The shifts. The very stuff you’re supposed to notice as a leader.

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Curiosity Is Not Indecision

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There’s this pressure in leadership to move fast and speak with confidence. To be sure. To act like you already know. But the best leaders I’ve ever worked with? They’re not afraid to sit in the uncertainty.

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They’re grounded enough to say, “I don’t know yet.” They stay open. They ask more than they answer.

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Because they’re not performing. They’re paying attention.

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Certainty wants applause. Curiosity wants understanding.

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One makes you louder. The other makes you better.

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Where I Am Now

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I’m not here to pretend I have everything figured out. I’m here to stay awake. To my team. To our clients. To the weird tension in a meeting that no one names but everyone feels.

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I want to ask sharper questions. Do not chase the perfect answer. I want to respond with thought, not just react with speed.

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It might not make me the fastest voice in the room. But I hope it makes me the one people trust when the path forward isn’t obvious.

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Stop Rewarding the Wrong Thing

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Here’s the truth. There’s no trophy for sounding the most sure. There’s only the work. The messy, honest, evolving work of leadership.

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And the leaders who do that work well? They’re the ones willing to question themselves. To pause. To keep showing up with curiosity, not ego.

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If you ask me, we need more of that.

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At StringCan, we help leadership teams step back from the noise, reframe the big picture, and move forward with purpose. If you’re ready to lead from clarity instead of control, let’s talk.

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