There is a moment on every climb when you stop looking up; a point in every race where you stop searching for the finish line. Not because the end is unimportant, and not because you are not tired, but you finally understand to the core of your being that the mountain, the race, is not ahead of you. It is underneath you, inside you, moving through you with every step.
That was the feeling I carried after my conversation with John Winsor.
Here is a man with a life scattered across continents and disciplines: athlete, writer, publisher, surfer, founder, survivor, widower, researcher, advisor to companies that shape the modern world. But when you listen closely, the through-line is not an achievement. It is not ambition. It is the quiet, persistent work of becoming.
John speaks about his life the way a seasoned climber speaks about a long route: the hard sections are never where you expect them to be. You can train for thin air and cold nights, but nothing prepares you for the day the mountain steals a partner, or the moment illness arrives without warning, or the season when every identity you’ve built falls away. Which rings so true with my experience of climbing, and of life. The expected highs were sometimes revealed to be the lowest lows. And the most important victories born of effort, of grinding, of grit.
Success on some days is simply surviving. Risk, John described it, is not the cliff’s edge. Risk is allowing yourself to stay open to all of it: the joy and the grief. The awe and the terror. The ending and the renewal. To remain open to all of this, and more, and still keep moving with the next honest step.
As I listened to John and contemplated his great successes and his lowest lows, I came to see a man who has stopped trying to outrun his own past. A man who has begun to understand that mastery and surrender are siblings, not opposites. Brother and sister born of the same deep yearning to feel fully alive. I found myself returning to something he said almost in passing: that the only true reality is the present moment, and everything else—our accolades, our failures, our stories about who we think we are—is just scaffolding around a single breath.
The mountains taught me that same lesson, though I learned it the hard way, clinging to identities long after they stopped serving me.
John learned it through heartbreak and reinvention, through being the “dumbest person in the room” and finding joy in it, through watching waves rearrange the shoreline and realizing that he, too, was allowed to be remade.
There was something oddly comforting in hearing a lifelong builder of companies who says he longs to be anonymous, to be the ghost in the machine, a bowl placed quietly at the threshold of the world. Not out of resignation, but out of equanimity.
The relief that comes when you stop needing to be seen to know you matter.
What strikes me most is this: we are all, in the end, explorers of the unseen. Some of us climb mountains. Some of us build systems. Some of us survive avalanches of grief or illness or change. John is leading us by example by learning to live with the truth that brilliance is abundant and opportunity is scarce, while the deepest opportunities, to love, to listen, to repair, to begin again, are available to us at every turn.
“Brilliance is abundant. Opportunity is scarce.” -John Winsor
John reminds us that a beginner’s mind is not a phase. It is a practice. A way of walking through the world as though everything can still surprise you, especially yourself.
He reminded me that courage is not momentum. It is attention.
It is the willingness to ask “why not?” when the rest of the world is busy defending the familiar.
He reminded me that being an elder is not about standing above younger generations, but kneeling beside them and offering whatever light you found along the way. And he reminded me, perhaps without knowing it, that the summit is never the point. The point is how we carry what we’ve learned back down to the valley and into the lives that need us. And when we look closely, we see that the valley and the summit are not opposites but simply points along the same continuum of life lived well.
The mountains tell us the truth: everything you are seeking is already here, in the breath you are taking, in the step beneath your feet, in the quiet courage it takes to let your old stories fall away so something new can rise.
And still, he believes the gap can be bridged. He’s building toward that now. Creating new pathways for ideas to meet opportunity. For talent, no matter where it’s born, to find the work it was meant for. For organizations to stop fearing AI and start using it to enable empathy, creativity, and shared success.
But beneath all of this—the research, the ventures, the tools—John is still the kid running ahead. He’s still chasing that feeling of a clean edge, a flat ski, a perfect glide. He’s still asking the same question:
Why not?
LISTEN TO THE EPISODE:
Exploring the poetic soul of the mountains.
Voice of the Mountains explores the mental and emotional adventures found in discovering who we are and what we’re capable of. Here we engage in self-reflection and humility, and embrace the beauty and struggle of the alpine experience equally.