The Midlife Chrysalis

Midlife isn’t falling apart. It’s asking for your attention.

In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlife crisis” and replaces it with a far more hopeful and powerful framework: midlife as a chrysalis, a necessary transition into a second adulthood.


Drawing from social science, psychology, and his own deeply personal story, Chip explains why midlife often feels like a breakdown, why it’s actually normal, and how it can become the most meaningful chapter of your life.

In this conversation, you’ll discover:

- Why happiness dips in midlife and rises afterward
- How identity loss and burnout are signals, not failures
- Why midlife hits men and women differently
- How wisdom and purpose often peak later in life


If you’re feeling burned out, disoriented, or quietly wondering, “Is this all there is?”, the answer, as Chip shows, is no. This is where something new begins.

👉 Watch now to understand what midlife is really asking of you and how to move from breakdown to transformation.


Timestamps:
01:20 The Origin of the Midlife Crisis Idea
04:40 The U Curve of Happiness
06:21 Why Midlife Is Not a Crisis
09:12 Becoming a Modern Elder
11:24 Chip’s Midlife Struggles
21:11 Why Midlife Lacks Support Systems
23:17 Biology vs Life Circumstances
25:49 How to Move from Crisis to Chrysalis
30:23 Watching People Self-Destruct in Midlife
34:18 Rebranding Midlife for the Future


Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeCrisis #MidlifeTransformation #SecondAdulthood #MidlifeWisdom #MidlifePurpose #ModernElder #MidlifeBurnout #HappinessCurve #LifeTransitions #MidlifePodcast #AgingWell #PersonalGrowth #MidlifeReset #LifeAfter40 #FindingPurpose

What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits down with California Governor Gavin Newsom for a rare, deeply personal conversation shaped by nearly 30 years of mentorship and friendship. This is not a political interview, it’s an honest exploration of midlife, identity, and becoming.Together, they reflect on:
How Gavin’s upbringing and dyslexia shaped his leadership
Why legalizing same-sex marriage became a defining moral moment
What the “winter years” between mayor and governor revealed
How fatherhood and midlife reshaped his relationship with power
Why grace, humility, and resilience matter now more than ever
Warm, thoughtful, and deeply human, this episode explores what’s possible when we slow down and listen. If you’re navigating change or reinvention, watch now and step into the chrysalis.
Timestamps:
03:26 Welcome to Midlife Chrysalis
04:06 Long friendship and early mentorship
05:54 Childhood and family background
08:48 Gavin’s writing experience
16:03 Becoming mayor of San Francisco
17:38 Decision to legalize gay marriage
25:11 Impact of marriage equality
27:54 Political winter as lieutenant governor
29:24 Identity loss and slowing down33:21 Humility and leadership lessons
35:22 Grace humility after years of division
38:46 The lost art of civil disagreement41:49 Political vision and building bridges
44:10 Stoicism and wisdom traditions
47:44 Fatherhood and authenticity
49:27 Wisdom bumper stickerLearn more about MEA at ⁠https://www.meawisdom.com/

What happens when success stops working and midlife hits hard?

Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement.

Blake opens up about:

- How selling part of TOMS triggered an unexpected identity collapse
- Why midlife depression often follows success, not failure
- The treatments and inner work that helped him recover, including ketamine therapy and TMS
- The simple but life-changing realization that shifted everything: “I am enough”
- Why connection and community matter more than success or status

👉 Watch now to hear Blake Mycoskie’s most vulnerable and meaningful story yet.


Timestamps:
01:11 Blake’s early entrepreneur journey
02:49 Reality Central and first major failure
04:59 The business lesson that shaped TOMS
07:49 Creating the one for one model
08:43 Selling TOMS and losing identity
12:36 Depression behind the public image
16:23 Searching for relief outside himself
17:24 Medication fog and deep isolation
19:30 Why telling others saved his life
20:54 Moving beyond traditional medication
21:12 Ketamine and TMS
25:53 Discovering the core wound
28:49 India and lasting inner freedom
33:27 Launching the Enough initiative
35:58 I’m Enough ritual poem
37:57 How the nonprofit model works
38:47 The growing mental health crisis
43:13 Self compassion and flow state
46:28 How to support someone in depression
51:54 Living with fear of relapse
54:17 Wisdom bumper sticker


Learn more about MEA at ⁠https://www.meawisdom.com/

#BlakeMycoskie #MidlifeCrisis #MentalHealthAwareness #EntrepreneurMentalHealth #SuccessAndDepression #TOMSFounder #MidlifeJourney #DepressionRecovery #FindingPurpose #SelfWorth #MentalHealthPodcast #MidlifeTransformation #HealingJourney #MenAndMentalHealth #IAmEnough

What if aging alone isn’t the only option?

As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude?

In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe to address loneliness, gray divorce, and the realities of solo aging.

In this episode, you’ll learn:

- Why more women are aging solo in midlife
- Why social connection matters more than health hacks
- How housing no longer fits modern midlife needs
- What Golden Girls–style living could look like in practice

This isn’t a finished solution — it’s a timely experiment that reimagines how we live and age.

👉 Watch now and decide if community belongs in your next chapter.


Timestamps:
02:40 Golden Girls homes concept
03:41 Gray divorce and solo agers
06:20 Loneliness and housing mismatch
08:05 Why Golden Girls homes now
10:10 The Santa Fe pilot homes
12:49 Workshops and community vision
15:29 What the research revealed
18:14 Matching roommates and house culture
21:10 Affordability and rental model
24:10 What about men
26:36 Long term vision and legacy
29:21 How to get involved
29:55 Final reflections


Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #GoldenGirlsHomes #MidlifeTransition #SoloAgers #GrayDivorce #LonelinessEpidemic #IntentionalLiving #MidlifeCommunity #WomenOver50 #AgingWell #CommunityLiving #ModernElders #MidlifeWisdom #HousingInnovation #SocialConnection

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson, pastor, former Louisiana legislator, and author of Aging While Black, to explore why aging isn’t a race-neutral experience and what it really means to age well in a system that was never built for everyone.Ray shares a simple, powerful way to rethink aging through community, innovation, and shared wisdom across generations.

In this episode, you’ll learn:
Why aging while Black carries unique structural and economic realities
How the village concept and Sankofa help bridge past, present, and future
Why technology and mutual mentorship matter for aging well
What collective longevity looks like across generations
This conversation invites us to rethink aging, equity, and how we care for one another at every stage of life.

Watch now and join the conversation. 

Timestamps:
03:02 Three pillars of aging while black
05:43 The village concept and African origins
08:18 Ubuntu and community identity
11:11 The Black church as a village
13:07 Embracing innovation and technology
18:39 Sankofa and learning from the past
24:38 Intergenerational circles and family wisdom
27:35 Collective longevity across generations
33:08 Keeping hopeful and building systems
39:50 Sources of inspiration and leadership
43:20 What makes aging while black different
51:03 Wisdom bumper sticker
53:27 Closing thoughts and workshop invitation 
Learn more about MEA at ⁠https://www.meawisdom.com/