Episode 183: The Midlife Awakening You Didn’t Know You Needed

WITH CHIP CONLEY

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What if midlife wasn’t a crisis… but a chrysalis?

This week, we’re talking with the legendary Chip Conley — New York Times bestselling author, hotelier, and modern wisdom keeper — about the true power and purpose of midlife. After founding the iconic Joie de Vivre hotel brand and later helping transform Airbnb as Head of Global Hospitality + Strategy, Chip experienced a life-altering wake-up call that changed everything. And it led him to create the Modern Elder Academy (MEA), the world’s first midlife wisdom school.

In this deeply inspiring conversation, Chip redefines what it means to age, grow, and become — showing us how midlife can be one of the most transformational, purpose-filled chapters of our lives. If you’ve ever asked, “Is this it?” or “Am I too late?” this episode is your soul’s permission slip to dream again.

We talk about:

  • Chip’s awakening moment (including a literal NDE)

  • Why midlife can feel like falling apart—and why that’s a good thing

  • The truth about midlife transitions (and why they’re often misunderstood)

  • The U-curve of happiness and why 47 is often our low point

  • The magic behind MEA and what it offers at any age

  • Wisdom vs. knowledge — and how to cultivate both

  • How to embrace change, purpose, and possibility in midlife (and beyond)

  • How to start your own “modern elder” journey

Whether you’re in your 30s, 40s, 50s or beyond, this episode is an invitation to see aging as expansion. Midlife isn’t an ending — it’s a beginning.

MORE FROM CHIP CONLEY

Chip Conley Photo credit: Lisa Keating Photography

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Episode 161: Burnout to Breakthrough – How an ESPN Reporter Found Her Way Back to Herself