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Gavin Newsom on Leadership, Identity, and Becoming Yourself
Gavin Newsom on Leadership, Identity, and Becoming Yourself

Season 1 Episode 57

What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits do…

6 months ago

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He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie
He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie

Season 1 Episode 56

What happens when success stops working and midlife hits hard?


Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapt…

6 months, 1 week ago

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Could Golden Girls–Style Living Be the Future of Midlife Housing?
Could Golden Girls–Style Living Be the Future of Midlife Housing?

Season 1 Episode 55

What if aging alone isn’t the only option?


As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose comm…

6 months, 1 week ago

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Aging While Black: Paying the Price of a Broken System | Ray Jetson
Aging While Black: Paying the Price of a Broken System | Ray Jetson

Season 1 Episode 54

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Agin…

6 months, 1 week ago

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How Conscious Capitalism Changes the Way Leaders Think | Rand Stagen
How Conscious Capitalism Changes the Way Leaders Think | Rand Stagen

Season 1 Episode 53

Most leaders are chasing short-term wins and missing the long game.

In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leaders…

6 months, 2 weeks ago

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Why Leadership Fails When Wisdom Walks Out
Why Leadership Fails When Wisdom Walks Out

Season 1 Episode 52

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom.


In…

6 months, 2 weeks ago

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From Breakdown to Wholeness: The Hero’s Path Through Midlife with Ben Katt
From Breakdown to Wholeness: The Hero’s Path Through Midlife with Ben Katt

Season 1 Episode 51

Have you ever reached a point in life where what once worked… suddenly doesn’t?


In this warm conversation with Chip, Ben Katt, MEA’s faculty in reside…

6 months, 2 weeks ago

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Jeff Krasno & Schuyler Grant: What Midlife Health Really Requires
Jeff Krasno & Schuyler Grant: What Midlife Health Really Requires

Season 1 Episode 50

What if the wellness advice you followed for years stops working after 50?


In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, a…

6 months, 3 weeks ago

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Stop Starting Over: How to Build Habits That Actually Last
Stop Starting Over: How to Build Habits That Actually Last

Season 1 Episode 49

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly…

6 months, 3 weeks ago

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Why Transitions Break Us and Heal Us | Kari Cardinale
Why Transitions Break Us and Heal Us | Kari Cardinale

Season 1 Episode 48

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to e…

6 months, 3 weeks ago

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