What if the most important part of leadership begins after your biggest win?
In this episode, Chip Conley, Founder & Executive Chair of Modern Elder Academy, shares the arc of his 30+ year career from founding 52 boutique hotels through culture-led hospitality, to mentoring Airbnb founders while shaping global travel strategy, to building one first wisdom schools in Baja dedicated to relevance through curiosity and community.
You’ll hear how letting go of old identities becomes leverage, culture becomes legacy, and relevance is crowdsourced through contribution.
Tune in to learn how one leader bridged hospitality into legacy, reshaped relevance without hierarchy, and built purpose as a lifelong leadership currency.
Key Takeaways:
- The Power of Letting Go: Why releasing old identities fuels your next reinvention
- Curiosity as Legacy: How staying curious keeps leaders visible across generations
- Purpose as a Practice: Curating meaning that outlasts applause and peaks
- Leadership Reimagined: Creating cultures of belonging through reinvention and inquiry
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Highlights
The key moments in this episode are:
[00:27] Personal Stories of Grief and Resilience
[01:13] Chip Conley's Career Journey
[02:36] Mentorship and Midlife Wisdom
[03:13] Early Life and Career Beginnings
[04:00] The Power of Authenticity
[05:43] Challenges and Triumphs in Leadership
[08:09] Purpose and Midlife Reflections
[13:43] Creating Inclusive Workplaces
[21:02] The Emotional Atlas of Place
[21:54] Discovering My Introverted Side
[33:43] Generational Differences in the Workplace
[41:50] Lightning Round and Final Thoughts -
Lightning Round
Q: What book has greatly influenced you?
A: Man’s Search for Meaning by Victor FranklQ: What is your favorite inspiring quote or saying?
A: The price of anything is the amount of life you exchange for it by Henry David ThoreauQ: What is one word or moniker you would use to describe yourself?
A: Social alchemistQ: What is one change you've implemented that made your life better?
A: At 47, after his flat-line experience where he died nine times over 90 minutes from an allergic reaction to an antibiotic, he learned he could let go of the founder/CEO identity that had defined him for 24 years, choosing personal lifestyle and authentic living over delayed financial gain.Q: What power song would you want playing as you walk out onto a stage?
A: Lovely Day by Bill Withers -
Quotes
Purpose is the second most important variable for living a longer, healthier, happier life.
Chip Conley
If you have a why, you can deal with any kind of how.
Chip Conley
Beauty and awe can only be seen when you slow down.
Chip Conley
We are supposed to learn how to curate a life with lots of small-P purposes.
Chip Conley
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About
Chip Conley is on a midlife mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the U.S., and then as Airbnb’s Head of Global Hospitality and Strategy, leading a worldwide revolution in travel, Conley co-founded MEA (Modern Elder Academy) in January 2018 in Baja California, Mexico.
Inspired by his experience of intergenerational mentoring as a ‘modern elder’ at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing start-up to the world’s most valuable hospitality brand, MEA is the world's first ‘midlife wisdom school’ and recently opened a campus on a 2,600-acre regenerative horse ranch in Santa Fe, New Mexico in May 2024. Dedicated to reframing the concept of aging, MEA supports students to navigate midlife with a renewed sense of purpose and possibility.
A New York Times bestselling author, Conley's seventh book "Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age" is about rebranding midlife to help people understand the upside of this often-misunderstood life stage. In the week of Chip's launch of "Learning to Love Midlife" in January 2024, he was featured as a guest on both "Good Morning, America" and "The Today Show" and the book rose to the #1 Happiness/Self-Help book on Amazon.