
Why Love Requires Skills Most People Never Learn | Terry Real
Why do so many relationships lose intimacy over time, even when love is still there?In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relat...
23 Mar 47min

Pete Holmes on Psychedelics, God & Finding Meaning in Midlife
The moment that breaks your life can also be the moment that transforms it. In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly...
20 Mar 1h 1min

Midlife Pit Stop: Refuel Before the Next Chapter
What if the most powerful move you could make at midlife… is to pause?In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more p...
18 Mar 26min

Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
Most of us try to solve midlife. What if that’s exactly the wrong approach?In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one...
16 Mar 57min

Why You Keep Repeating the Same Conflict Patterns | Diana Chapman
Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead.In this episode of Midlife Chrysalis, ...
13 Mar 56min

From Ego to Soul: Rewriting the Second Half of Life
The drive that made you successful may not be meant to lead you forever.In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the de...
11 Mar 24min

Mortality Was My Wake-Up Call | Dr. Brad Jacobs
What if the real key to longevity isn’t a biohack but a wake-up call?In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly help...
9 Mar 55min

Why Midlife Feels Like Exile And Why That’s a Gift | David Whyte
In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meanin...
6 Mar 1h 3min



















