Midlife isn’t the end of the story, it’s the chapter where something new wants to begin.In this episode of Midlife Chrysalis, Chip Conley sits down with Pam McLean, pioneering coach, co-founder of the Hudson Institute of Coaching, and a guiding voice on adult development and the “bonus years.”

Together, they explore why midlife isn’t about stepping back, but about letting go and moving forward with intention.

Pam shares:

• Why releasing old identities is essential for growth
• What the “bonus years” make possible at any age
• How Life Forward helps reframe change as opportunity
• Why discomfort, grief, and curiosity are part of becoming
• What truly makes a great coach — in life and in leadership

This is a warm, thoughtful conversation for anyone standing at a crossroads and wondering what comes next. Watch now and discover how midlife can become a powerful new beginning.

Timestamps:

03:32 Pam’s early life and background

04:17 From clinical psychology to coaching

07:06 How coaching has developed

09:31 Life Forward and Hudson Institute

11:46 The midlife happiness curve

14:53 Cancer as a life teacher16:06 Hudson Institute and MEA connection

18:08 Letting go of old identities

21:50 Navigating major life transitions

26:27 Why experimentation matters

27:39 Men vs women in midlife

31:01 What makes a great coach

33:47 Why people choose coaching

35:15 Gender balance in coaching35:51 Coaching in the age of AI

38:20 How to choose the right coach

40:38 Creativity later in life

42:41 Wisdom bumper sticker

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

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/

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 Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power.

Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meaning.

You’ll learn:

- Why short-term thinking undermines great leadership

- What it means to play the infinite game

- How awareness creates better choices

- Why the best leaders think in decades, not quarters

If you’re leading others, or rethinking your own direction, this conversation offers a clear, grounded reframe.

👉 Watch now and start playing the long game.

Timestamps:

05:51 Rand Stagen personal leadership journey

07:47 The advice for young entrepreneurs

10:17 Entrepreneurial roots and early influences

12:43 Founding the Leadership Academy

16:50 Structure of the leadership program

22:23 Integral theory explained

26:18 Leadership and polarization

35:57 Practical advice for leaders

41:45 Conscious Capitalism principles

45:41 Short term versus long term thinking

52:01 Workshop goals and takeaways

56:18 Who the workshop is for

58:12 Leadership wisdom and closing insight

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

#LeadershipDevelopment, #ConsciousLeadership, #LongTermThinking, #LeadershipMindset, #PersonalGrowth, #ExecutiveLeadership, #PurposeDrivenLeadership, #InfiniteGame, #MidlifeLeadership, #SelfLeadership, #LeadershipPodcast, #AwarenessAndChoice, #ModernLeadership, #LeadershipWisdom, #ChipConley

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

In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim it.

In this episode, you’ll learn:

- Why leadership is a practice, not a personality trait

- How culture is shaped when leaders aren’t in the room

- What companies lose when institutional wisdom disappears

- The difference between knowledge workers and wisdom workers in the AI era

As technology accelerates, human skills become the real competitive edge.

👉 Watch now and discover how wisdom future-proofs leadership and culture.

Timestamps:

00:13 Leadership as a practice

02:29 Culture leaders overlook

05:18 Defining real company culture

08:57 Institutional wisdom loss

13:47 Knowledge workers vs wisdom workers

18:30 AI impact on early careers

22:22 Humanities and philosophy comeback

22:44 Wisdom at Airbnb

25:53 Informal mentors and EQ

27:57 Leading yourself first

28:18 Resources and upcoming workshop

30:12 Closing thoughts

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

#LeadershipWisdom #WisdomAtWork #FutureOfLeadership #AIAndLeadership #CompanyCulture #EmotionalIntelligence #KnowledgeVsWisdom #HumanSkills #MentorshipMatters #InstitutionalWisdom #LeadershipDevelopment #WisdomWednesday #LeadershipCulture #AIImpact #ModernLeadership