Chip Conley: Why Success Isn't Enough, the Power of Midlife Reinvention & the Art of Not Waiting

He built a boutique hotel empire, helped Airbnb become a global powerhouse, and founded the world's first midlife wisdom school. But Chip Conley's greatest transformation began when he died. Nine times. At 47, Chip flatlined nine times over 90 minutes following a severe allergic reaction to an antibiotic. What he experienced during those terrifying moments would eventually change everything he believed about success, ambition, and what it means to live a meaningful life. In this extraordinary conversation, I sit down with Chip Conley, bestselling author, former Airbnb executive, and founder of the Modern Elder Academy (MEA), to explore a question that haunts so many accomplished people: What happens when the life you've worked so hard to build no longer feels like the life you want to live? Chip shares why so many successful people remain trapped by their own identities, what living with cancer has taught him about holy urgency, and why he's redefined ROI from return on investment to "ripple of impact." We explore the psychology of reinvention, the fear of letting go of who we've been, and why midlife may actually be our greatest opportunity to become who we're meant to be. And we confront a question at the heart of my work with MORE: What are you postponing? Chip also reveals why he once considered himself an "admiration addict," the daily mantra that helps him separate his self-worth from his achievements, and a practical exercise anyone can use to envision and begin creating a more fulfilling future. This isn't just a conversation about getting older. It's about getting wiser, redefining success, and finding the courage to live differently before life forces your hand. Because you don't have to abandon ambition to live a more meaningful life. You might just need to reconsider what you're ambitious for. And you shouldn't have to nearly die to discover that. Learn more about Chip at chipconley.com and the Modern Elder Academy at MEAwisdom.com. Learn more about MORE at bemorealigned.com.