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Between youth and old age lies this incredibly rich stage of life that remains curiously under-examined and wildly underappreciated: midlife.
Too often, we view this period solely through the lens of crisis rather than recognizing the profound opportunities it presents.
What if the years between 35 and 75 aren’t meant for crisis but for chrysalis—a transitionary phase where we shed our identities, let go of endless striving, and emerge with deeper purpose and meaning?
My guest today is Chip Conley, a hospitality maverick and the founder of Modern Elder Academy—the world’s first midlife wisdom school. At 26, he created Joie de Vivre, which grew into America’s second-largest boutique hotel company. However, it was a near-death experience at 47—literally flatlining nine times in 90 minutes—that catalyzed his most consequential transformation. After selling his company, he joined Airbnb as their “modern elder,” mentoring CEO Brian Chesky while simultaneously learning a new industry from colleagues often half his age.
“Our past life lessons are often the painful raw material for our future wisdom.”
– CHIP CONLEY
Today, we discuss:
- Transforming Midlife Crisis to Chrysalis
- The Shift from Ego to Soul at Midlife
- Friendship as a Wellness Practice
- Wisdom vs. Knowledge in Modern Culture
- Five Questions Every Midlifer Should Ask
For those who prefer a visual experience, the conversation is available on YouTube. As always, the audio version streams wild and free on Apple Podcasts and Spotify.
Note: Chip and I invite you to experience these insights in person in Los Angeles on June 5th for a special gathering with the MEA faculty. Register at meawisdom.com/richroll.
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- Connect with Chip: Website | Facebook | Instagram | Twitter
- Book: Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age
- Books: Chip Conley
- Chip Conley: FREE Midlife Check-Up to Understand What Gets Better With Age
- Modern Elder Academy: About
- Modern Elder Academy: Upcoming Retreats
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Thank The Team: I do not do this alone. Send your love to Jason Camiolo for audio engineering, production, show notes and interstitial music; with additional audio engineering by Cale Curtis and additional music by Moby; Dan Drake & Morgan McCrae for video, & editing; graphics by graphics by Alejandro Ribadeneira & Bryan Lawrence; portraits by Davy Greenberg; copywriting by Ben Pryor; and theme music by Tyler Piatt, Trapper Piatt & Hari Mathis.
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