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“One conversation could change your life, and you just never know when it’s going to happen.”
That line was offered over coffee by a peer I admire. It landed. Quietly, but with weight. In business, let’s be honest, real breakthroughs rarely come from a spreadsheet or strategy deck. They come from a sentence, a story, a conversation that shifts your perspective and opens a door you didn’t know existed.
But those moments only happen if you’re paying attention — if you’re open. And above all, if you’re willing to say yes.
The sharpest leaders I know treat success like a syllabus — never complete. They stay curious. They listen well. And they build careers not just on instinct, but on integrity. That’s been my own playbook, though it was never planned. My career has jumped industries from Formula 1 to private aviation, to superyachts, and now a Membership Club rooted in community.
Not one of these chapters began with a cold pitch. They came from conversations — warm, uncalculated — human.
More often than not, these conversations didn’t happen in boardrooms or scheduled Zoom calls. They happened at the edge of a dinner party, once the name tags came off and the real conversation began. That’s when people stop pitching and start revealing. That’s when doors open.
Related: The Risky, Messy and Unstoppable Power of Saying ‘Yes’
When we’re young, saying yes isn’t brave — it’s instinctive. Think back to being the first to raise your hand, or the quiet pride of being chosen to write on the chalkboard. That instinct to step forward doesn’t fade in the people who go on to lead. They just keep leaning in. My advice: don’t grow out of that habit. It has served me well.
At some point, adulthood teaches us to calculate. We learn to hedge, to pause, to wait for the perfect set of conditions. But the truth is, the most formative moments often arrive dressed in ambiguity. They’re unscheduled, under-the-radar, sometimes inconvenient. That’s why saying yes — particularly when it’s easier to say no — still matters.
Not long ago, I was invited to the PathNorth Annual Gathering, a smart, unpretentious event curated by my friend Doug Holladay, author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life. The room was full of high-achieving, reflective people. One member, 90 years old and sharper than most CEOs, offered her secret: “Just say yes!” That simple phrase stuck with me and became my mantra.
So, I tried it.
That year, I said yes even more. To the Kentucky Derby, where I discovered the elegance and athleticism of horse racing. To the Arctic, where a polar bear stared me down and reminded me how small we are. To a village in Africa, where I was reminded that gratitude always outpaces privilege. I met people who challenged me, surprised me, and shifted my thinking. They made me a student again.
Related: What’s it Like to Have It All? Here’s What I Gained When I Stopped Trying to Be Perfect
I also found that saying yes didn’t always lead somewhere dramatic. Sometimes it led to a slower dinner, a longer conversation, or a change in pace. But the compound interest of those small yeses — the people they brought into my orbit, the ideas they unlocked—was impossible to ignore.
And occasionally, the yes wasn’t to someone else — it was to myself. To taking the risk. To revising an old idea. To stepping into the unknown just because it felt right.
Those memories, sharp, vivid and unexpected, exist because I said yes. So, when our marketing team pitched a podcast, I didn’t hesitate.
On A Life Well-Lived, I sit down with accomplished Exclusive Resorts Members, people like CAPT Jim “Guido” DiMatteo, Gray Malin, Tish Squillaro and Chef Thomas Keller, and unpack the choices behind the lives they’ve built. The through-line? They said yes when it counted. They kept showing up. They built reputations not on flash, but on follow-through.
And while their stories vary wildly — fighter pilot to photographer, entrepreneur to chef — what unites them is a quiet conviction: they don’t wait for permission. They pursue lives of meaning with an almost editorial precision, editing as they go.
Here’s what I’ve learned: curiosity doesn’t knock, it wedges doors open. The more you engage, the more the world seems to respond. If you take one thing from this, make it this: be the one to start the conversation. Ask better questions. Stay interested. Get comfortable being uncomfortable; that’s where growth lives.
And if you need a rule of thumb, here’s mine: Say yes to the invite. Say yes to the person who isn’t like you. Say yes to the thing that makes you a little nervous. That’s where all the good stories start — and all the best ones end up.
Because when you say yes — earnestly, openly, decisively — the right conversation really can change everything.
“One conversation could change your life, and you just never know when it’s going to happen.”
That line was offered over coffee by a peer I admire. It landed. Quietly, but with weight. In business, let’s be honest, real breakthroughs rarely come from a spreadsheet or strategy deck. They come from a sentence, a story, a conversation that shifts your perspective and opens a door you didn’t know existed.
But those moments only happen if you’re paying attention — if you’re open. And above all, if you’re willing to say yes.
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