Last week, sitting on a Lisbon terrace as the evening light painted everything gold, my son said something that stopped time. We’d been talking about his final year of college this upcoming year, about choices ahead, about all the ways life was pulling him forward. And then, quietly, Henry said: “I think I’m finally willing to not know what comes next and just say yes.”
That word. Willingness. It hung in the air between us.
Yesterday he left, and I’m still hearing it echo. Not just what he said, but what he meant. Because willingness is about saying yes even when you don’t know where it leads.
We live in a world obsessed with certainty. Five-year plans. Strategic roadmaps. Clear metrics and measurable outcomes. We’re taught to grip the wheel, control the variables, force the result.
But every breakthrough I’ve witnessed began with a moment of willingness. Not willpower. Not determination. Willingness.
The difference is profound. Willpower fights. Willingness flows. Willpower exhausts itself against resistance. Willingness finds the opening.
My son’s words keep returning to me because they point to something we’ve forgotten. That not knowing isn’t failure. It’s the soil where new possibilities take root.
In our hyperconnected, always-on world, not knowing feels dangerous. Like falling behind. Like losing control. So we fill every space with plans, predictions, and protective measures. We arm ourselves with knowledge until we can’t feel what’s actually happening.
This isn’t passive. It’s intensely active. Like an improv musician listening so deeply to the other players that they can improvise perfectly in real time. They’re not following a script. They’re following the music as it unfolds.
That’s what willingness does. It attunes us to what’s actually happening instead of what we think should happen.
Three months with my son in Lisbon wasn’t planned. He was only supposed to be here for two months but stayed longer. It gave us time for more conversations, his long walks through the cobblestone streets of Chiado, and such incredible moments together that I’ll never forget.
None of that would have happened without willingness.
What Henry understood in that moment is something most adults forget:
Uncertainty isn’t the opposite of security. It’s the birthplace of possibility.
As his plane lifted off yesterday, I felt something I hadn’t expected. Not sadness (although I was sporting some pretty leaky eyes), it was really gratitude.
And now he’s willing to step into his final year without a predetermined script. He’s learned to trust the current instead of fighting it.
That’s the gift that willingness gives us. Not certainty about where we’re going, but confidence in our ability to navigate wherever we find ourselves.
The question isn’t whether you are ready, it’s whether you are willing.
And if you are, if you can say yes to not knowing how it ends, everything becomes possible.
Are you willing?
Stay human
- Bryan
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You are reading BEing Human, a weekly newsletter about an honest exploration of trust and leadership from the bestselling author of Human-to-Human and Shareology, 3x CEO of Silicon Valley companies, and TEDTalker. Written by Bryan Kramer, an executive coach, mentor, and board advisor. Bryan walks with leaders and teams who have lost the plot and want it back.
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Beautifully said. By both of you.
“Uncertainty is the birthplace of possibility.” Wise words. I’m saving that.