Midlife and the Moral Pressure of Limited Time | Kieran Setiya
Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source of clarity rather than crisis. Our guest is Kiera...
27 Feb 1h 2min
What a Cancer Diagnosis Teaches You About How to Live
What happens when time stops feeling endless and starts feeling real?In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and ur...
25 Feb 28min
From Ambition to “I’m Enough” | Brian Chesky
In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO,...
22 Feb 1h 8min
Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross
Midlife isn’t a crisis. It’s an invitation to come alive again.In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Des...
20 Feb 51min
Why Midlife Friendships Stop Working & How to Fix Them
Ever notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common ...
18 Feb 19min
Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman
Ever wonder what happens when “success” still feels empty?At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself...
16 Feb 1h 3min
Why Friendship Becomes the Most Important Skill in Midlife | Jeff Hamaoui
Midlife rarely falls apart all at once. It slowly grows quieter, fewer close friendships, less community, more doing and less belonging.In this episode of Midlife Chrysalis, Jeff Hamaoui, MEA co-found...
13 Feb 58min
What Great Mentors Do Differently in Midlife
Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.In this Wisdom Wednesday episode, Derek and Chip explore how mentorship ...
11 Feb 20min
