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The Rich Roll Podcast

The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

The Rich Roll Podcast

Rich Roll

Health & Fitness, Education, Self-improvement, Society & Culture

4.812.9K Ratings

🗓️ 24 April 2025

⏱️ 128 minutes

🧾️ Download transcript

Summary

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical growth, addressing life's longest yet least understood phase. We discuss his near-death experience, the nature of wisdom, and why friendship becomes essential to wellness as we age. In the process, Chip creates space for me to reflect honestly on my own lifelong pursuit of achievement. Chip is a treasure. This exchange is for anyone seeking to avail themselves of midlife's deeper possibilities. Enjoy! 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.  Show notes + MORE Watch on YouTube Newsletter Sign-Up

Transcript

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0:00.0

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1:28.8

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1:32.3

Hey, everybody, over here, I need your full attention, because today's episode is brought to you

1:37.1

by On. Now, listen, confession here. I'm somebody who has spent many decades obsessed with hard metrics, actually measuring the

1:46.7

value of my life against the number of seconds I could shave off my splits or the distances I could

1:53.7

run and even the number of people my words and my voice could reach. But age and wisdom hard earned

2:00.6

have actually taught me a lesson.

2:02.8

And that lesson is that the hardness required to do hard things is only going to get you so far.

2:08.6

The best of what movement and even life has on offer is so much more about soft wins.

2:15.4

Because the victories that stick with you, I can tell you never have

...

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