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Midlife is a Chrysalis, Not A Crisis—Chip Conley On Why Life Gets Better With Age

By January 11, 2024No Comments
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Episode #806



What if we framed midlife not as a crisis but as a transformative chrysalis—a liminal period where profound awakenings unfold?

What if we saw it as an opportunity to shed old layers, unfurl our wings, and share the pollen of our wisdom with the world?

Guiding us from pupa to butterfly, we have the Monarch himself, Chip Conley. 

Returning to the show for the second time (Chip first appeared on episode 681), Chip founded the Modern Elder Academy, the pioneering midlife wisdom school dedicated to transforming aging. He is also a New York Times bestselling author. In his latest book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, Chip retools conventional notions of life in our 40s, 50s, and 60s. Drawing from the latest social science research, moving anecdotes, and enduring wisdom, he unveils 12 compelling reasons why life becomes more prosperous and fulfilling as we age.

In his earlier phase of life, Chip founded Joie De Vivre, America’s second-largest boutique hotel company, and served as the Strategic Advisor and Global Head of Hospitality for Airbnb, where he was the “modern elder” in guiding the newly-established start-up into the global hospitality hallmark it is today. Chip is a reserved public speaker and has delivered talks on the prestigious TED stage multiple times.

Today’s conversation revolves around how we conceptualize and define life stages, the concept of Age Fluidity, the age curve of happiness, and the importance of cultivating regenerative communities.

“Curiosity and being open to new experiences are the top variables in living a longer, happier, healthier life.”


We also explore Chip’s personal journey with cancer, the distinction between showing up and showing off, the role of being a conduit for ideas and collaboration, the essence of being a Modern Elder, the concept of age apartheid, and the value of generational dinners.

Chip, a steadfast change agent and true moral beauty provides practical guidance for navigating midlife and instills encouragement for the years to come.

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.

A special note: Chip generously extends a unique opportunity to listeners turning 50 this year—the chance to win a FREE three-night stay and tuition for 8 people (you and 7 of your friends) at the Modern Elder Academy Santa Fe Campus for the ultimate birthday party. To enter, write an essay about why you think life gets better with age, why you’re deserving, and how it will serve you at this particular time in your life and submit it to This incredible opportunity is only for listeners turning 50 in 2024.

For individuals seeking to infuse greater purpose and satisfaction into their professional journey, especially those who have dedicated a significant portion of their career to a specific path and are now pondering fresh opportunities, this conversation is a must.


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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; Blake Curtis & Dan Drake for video, & editing; graphics by Jessica Miranda & Daniel Solis; portraits by Davy Greenberg, Grayson Wilder & Gizelle Peters; video clips for social media are created by AJ Akpodiete; copywriting by Georgia Whaley; and theme music by Tyler Piatt, Trapper Piatt & Hari Mathis.

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