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    Education

    The Midlife Chrysalis

    The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife.

    Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

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    Latest Episodes:
    Why Rituals Matter More Than Routines in Midlife Jan 28, 2026
    Show notes

    What if the way you start your morning is quietly shaping how your whole day feels?


    Chip Conley sits down with Derek Gehl to explore why so many midlife routines start to feel empty and how turning them into simple, meaningful rituals can bring more calm, clarity, and purpose to everyday life. Together, Chip and Derek share:

    • Why routines can feel mechanical, while rituals help us feel present and changed
    • How to gently layer meaning onto things you already do, like showering or stretching
    • Why small morning rituals can boost mood, energy, and emotional well-being
    • How affirmations work best when they’re personal, specific, and emotionally real
    • Easy ways to create micro-rituals that set a better tone for your day

    If midlife has you longing for more intention without adding more to your plate, this episode is a friendly invitation to start small and start with your morning.


    Give it a listen, try one simple ritual this week, and notice what begins to shift.


    Timestamps:

    02:12 Morning rituals vs routines

    02:28 Routine vs ritual

    04:00 Shower meditation prayers

    05:48 Affirmations and new stretching ritual

    11:21 The impact of morning rituals12:27 Accountability and consistency

    14:01 Rituals as landmarks and micro rituals

    15:24 How to create your own rituals

    17:07 Science and specificity of affirmations


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


    How Ritual, Awe, and Community Bring Midlife Back to Life | Christine Sperber Jan 26, 2026
    Show notes

    In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and community can bring us back to life in midlife.

    Drawing from ski town culture, life in Baja, and years of building transformational experiences, Christine offers a hopeful reframe of aging as something to design, not fix.


    In this conversation, Chip and Christine explore:

    • Why purpose matters more than productivity in midlife
    • How simple rituals create meaning, resilience, and belonging
    • What nature, movement, and community teach us about vitality
    • Why transitions like perimenopause and loss call for compassion, not hustle

    If midlife feels like a pause, a question mark, or an invitation to something more, this episode will leave you feeling seen, grounded, and hopeful.Listen now and rediscover what it means to feel fully alive in midlife.


    Timestamps:

    03:22 Christine Sperber’s background

    06:55 Leaving Colorado for Baja

    08:49 First experience of Baja and Pescadero

    10:59 Freedom and living in rhythm with nature

    15:15 Experience design and creating meaningful gatherings

    17:48 Baking bread as ritual and collective practice

    22:14 Origin story of MEA

    24:02 Early doubts and building a local economy

    26:07 Lessons from the first MEA beta cohorts

    30:38 Ski towns, purpose, and longevity research

    33:46 Aging, vitality, and midlife perspective

    40:49 Introversion, ritual, and reclaiming time

    46:19 Third vault conversations and authentic community

    48:26 Moral beauty as a pathway to awe

    54:11 Transformation through deep connection

    56:19 Designing belonging and social bonds

    57:28 Wisdom bumper sticker


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



    The Bonus Years: Midlife Is About Reinvention Not Retirement | Pam McLean Jan 23, 2026
    Show notes

    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 a Transformation Jan 21, 2026
    Show notes

    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


    Gavin Newsom on Leadership, Identity, and Becoming Yourself Jan 19, 2026
    Show notes

    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/


    He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie Jan 16, 2026
    Show notes

    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


    Could Golden Girls–Style Living Be the Future of Midlife Housing? Jan 14, 2026
    Show notes

    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 While Black: Paying the Price of a Broken System | Ray Jetson Jan 12, 2026
    Show notes

    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/


    How Conscious Capitalism Changes the Way Leaders Think | Rand Stagen Jan 09, 2026
    Show notes

    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


    Why Leadership Fails When Wisdom Walks Out Jan 07, 2026
    Show notes

    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


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