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- It's never to late to reinvent yourself (Chip Conley - Modern Elder Academy, Airbnb, Joie de Vivre)
It's never to late to reinvent yourself (Chip Conley - Modern Elder Academy, Airbnb, Joie de Vivre)
Chip mentored Airbnb's founders, now he's teaching others how to become elders
Scott Britton
August 14, 2025
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“Part of the reason I created MEA was to create the first institution dedicated to distilling wisdom in the modern age. You know, back in the days of the Greeks, and there were mystery schools and wisdom schools back then. But we, in the last couple hundred years, have been so focused on colleges and universities and about filling our heads with knowledge. And it's all good. That's nothing wrong with that. Except in the era of AI, all of that knowledge is on my little phone in my pocket. So knowledge is commodity and wisdom is a scarcity and what's scarce is usually valuable.” (44:15 in this cast)
Chip Conley is the founder of Modern Elder Academy, the world's first midlife wisdom school, and a bestselling author who has become the leading voice on conscious aging and midlife transformation. Before creating this revolutionary educational platform, he spent 24 years building Joie de Vivre into the second-largest boutique hotel company in the US then joined Airbnb at age 52 as the strategic advisor to the founders. He helped guide the startup to become the world's most valuable hospitality company.
In this conversation, we explore Chip's complete reinvention journey and the practical framework he's developed for midlife transformation. We discuss the neuroscience of aging, the shift from ego to soul-driven living, and how to leverage accumulated wisdom in new contexts.
I've always been fascinated by people who successfully reinvent themselves, especially later in life when it seems riskier and harder. Chip represents the gold standard. His journey from hotel mogul to tech sage to wisdom educator offers a practical blueprint for anyone feeling stuck in their current identity and ready for something new.
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This episode is great for:
Anyone experiencing what feels like a midlife crisis
Entrepreneurs and business leaders curious about how wisdom and experience can become competitive advantages rather than liabilities
People feeling disconnected from their authentic selves
Those interested in intergenerational mentorship
Spiritual seekers exploring the ego-to-soul transition
Anyone supporting someone through midlife transitions
Leaders looking to build more age-diverse teams and tap into the unique strengths that come with different life stages
Ideas that really stuck out to me:
Midlife reinvention follows a predictable three-act structure. Chip's transformation wasn't random but followed clear phases. The Builder (Joie de Vivre era), The Sage (Airbnb era), and The Wisdom Keeper (Modern Elder Academy era). Each phase built on the previous one while expressing a different aspect of his evolving identity. Understanding this structure helps normalize the process and provides a roadmap.
The key is shifting from ego-driven to soul-driven living. Around midlife, our primary operating system naturally wants to change from ego that seeking external validation to soul seeking internal wisdom. Fighting this shift creates suffering. Embracing it creates transformation.
You don't need to blow up your life to reinvent yourself. Chip didn't abandon everything he'd learned. Instead he found new contexts to apply his accumulated wisdom. From hospitality to tech to education, his core skills remained relevant while his expression evolved. Smart reinvention is about transferring your capabilities not starting from zero.
The modern elder mindset is the secret sauce. He defines a modern elder as someone who's as curious as they are wise. This alchemy of openness and experience creates unique value. You become both your own student and teacher. His mindset allows you to contribute wisdom while staying fresh and relevant.
Successful reinvention requires changing your success metrics. Chip shifted from ROI (return on investment) to ROI (ripples of impact). Instead of asking "What can I get?" he started asking "What can I give?" This isn't just philosophical but practical. Your new identity needs new measurements to guide decisions and track progress.
Age apartheid limits everyone's potential. Most people's five closest friends are within 10 years of their age. This artificial segregation deprives younger people of wisdom and older people of fresh perspectives. Breaking these barriers accelerates learning and creates unexpected opportunities for collaboration and growth.
The brain actually gets better at certain things with age. We move from fluid intelligence (fast, focused problem-solving) to crystallized intelligence (connecting dots, systems thinking). Arthur Brooks calls this the four-wheel drive of the brain where you can be both logical and lyrical simultaneously. This neurological upgrade makes midlife reinvention not just possible but advantageous.
Wisdom is the new competitive advantage. In an AI world where knowledge is commoditized wisdom becomes scarce and valuable. The ability to distill life lessons into practical guidance becomes increasingly precious as information becomes abundant.
What really strikes me about our conversation is how he highlighted this massive blind spot in our society. We have elaborate support systems for teenagers going through adolescence but we offer virtually nothing for adults navigating the equally predictable crisis of midlife. We essentially abandon them to struggle alone or numb the discomfort with medication.
Chip didn't just survive his transformation but turned it into his life's work. That's the mark of true wisdom and the real magic. In an age where knowledge is commoditized by AI the ability to metabolize experience into wisdom becomes our most valuable currency.
His journey demonstrates that midlife reinvention isn’t just possible, it's inevitable. The question isn't whether you'll transform but whether you'll do it consciously or unconsciously with grace or with struggle.
Remember that the caterpillar doesn't know it's going to fly. It just knows something is dying. Trust the process. Your wings are coming.
I hope you enjoy this conversation!
- Scott
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Episode Transcript
Show Notes
00:00 - Introduction & Defining the Modern Elder
01:38 - From Ego to Soul
03:31 - A Near-Death Wake-Up Call
05:34 - The U-Curve of Happiness
09:20 - Midlife Crisis or Midlife Chrysalis
13:20 - Redefining Midlife
16:19 - Self-Worth, Bracing, and Overachievement
19:00 - From Attaining to Attuning
22:02 - Resilience vs. Adaptability
23:37 - Can You Achieve from Attunement?
27:23 - Lessons from Airbnb
30:55 - Ripples of Impact
34:22 - Living Soul-Led
39:30 - Where Are the Elders?
43:15 - Sharing Wisdom Across Generations
45:15 - Knowledge vs. Wisdom