Maybe you built something remarkable. Maybe you sold your company, stepped away from a role that defined you for years, or simply reached an inflection point you’ve been climbing toward your entire career.
And now comes the question no one warned you about: What now?
During my 25-year career coaching Fortune 500 CEOs, startup founders, and heads of state through more high-stakes moments than I can count, I’ve navigated some tough conversations. But some of the toughest ones I’ve had haven’t been about crisis management, bankruptcies, or lost elections. They’ve been with the people who won what they most wanted and later felt strangely lost because of it.
The pattern is remarkably consistent. When a leader who’s spent decades in relentless pursuit of a goal finally achieves it, the champagne gets popped, and the congratulations roll in. “You did it!” everyone exclaims. But then, sometimes within weeks, an eerie feeling sets in. It’s not depression, exactly. It’s more like a low-grade existential hum. The phone has stopped buzzing, and the calendar is suddenly empty in a way that feels less like freedom and more like freefall.
This is the irony of success no one talks about. When your work once provided your purpose, your community, your daily structure, and your sense of self—what happens when that’s gone?
Most people in this position do one of two things. They either immediately jump into the next thing, chasing the dopamine of achievement they know so well. Or they drift, saying yes to opportunities that look impressive but feel hollow.
But neither path leads to fulfillment.
What’s really needed is something most high achievers have never practiced: sitting in the uncertainty long enough to discover what genuinely matters to them. Not what should matter, not what would impress others, but what actually stirs something alive in them.
That’s why I partnered with Chip Conley to create a workshop called “What Now? Finding Passion and Purpose After a Big Success.” We’re hosting it for the second time at MEA’s stunning oceanfront campus in Todos Santos, Mexico on March 9-14, 2026.
When I came up with the concept for this retreat in 2023, I took it right to Chip for a host of reasons. He built Joie de Vivre Hospitality into the second-largest boutique hotel company in America, sold it, then reinvented himself at Airbnb before founding the Modern Elder Academy at 52. He’s not theorizing about post-success reinvention; he’s living it, publicly and vulnerably.
Together, Chip and I have designed a five day curriculum that combine MEA’s proven core material with a number of deep coaching frameworks I typically reserve for my one-on-one engagements with global leaders. The goal isn’t to hand you a new business plan or a tidy five-year roadmap. It’s to help you cut through the noise, the expectations, the “shoulds,” the pressure to keep performing, and reconnect with what actually energizes you.
Throughout the week, you’ll work in small groups with other accomplished peers who understand this particular moment as deeply as you do. No surface-level networking. No new startup pitches. Just honest conversations with people who’ve been where you are and are ready to figure out what’s next.
By the end of our time together, we hope you’ll have clarity about your “second mountain.” That next chapter defined not by ambition alone, but by purpose, depth, and meaningful connection. And even if you don’t have perfect clarity, you’ll be armed with tools and frameworks to get you there as our work together integrates in the months that follow.
If you’ve been circling the same questions for months or years, “What Now” might be just the catalyst you need. You’ve earned the right to choose something that feels genuinely fulfilling.
Let’s figure out what that is…together. I hope you’ll join us!