The Midlife Chrysalis

Chip Conley
  • 4.9 (82)
  • Self-Improvement
  • Updated Weekly

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.

  1. 1d ago

    Will Life Break You Open or Close You Off? | Elizabeth Lesser

    After everything you’ve been through, keeping your heart open can feel like a lot to ask. But there’s still room for connection, beauty, and a life that feels more like you. Author and Omega Institute cofounder Elizabeth Lesser joins Chip Conley to explore how divorce, loss, and aging can deepen our lives without hardening our hearts. Drawing on her books Broken Open and the forthcoming Stay Open, she shares insights on how to: Find new possibilities when your old life falls apart.Question the stories that keep you apart from people you love.Make room for joy and grief at the same time.Meet your aging body with kindness and care.Stay open while holding healthy boundaries. Join Chip and Elizabeth for a heartfelt conversation about what it takes to stay soft, stay curious, and keep growing through life’s changes. Timestamps: (02:37) What Is the Soul? (05:47) Let Your Soul Lead in Midlife (08:45) When Life Breaks You Open (11:54) The Stories That Keep Us Apart (13:40) How to Have Difficult Conversations (18:00) How to Stay Open When Life Is Hard (24:03) Finding Beauty Alongside the Pain (26:20) Growing Older, Becoming More Whole (28:47) What Gets Better With Age (32:59) How Omega Institute Began (38:13) Behind the Scenes of a Retreat Center (42:30) Do No Harm, but Take No Shit Learn more about MEA at ⁠https://www.meawisdom.com/ Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate #ElizabethLesser #ChipConley #MidlifeChrysalis #BrokenOpen #StayOpen #OmegaInstitute #MidlifeTransformation #HealthyAging #PersonalGrowth #EmotionalHealing #SpiritualGrowth #Relationships #GriefAndLoss #SelfCompassion #Boundaries

  2. 3d ago

    When Everything Hits at Once: The Art of the Reframe

    “Stay positive” can feel hollow when cancer returns, someone you love dies, and your marriage is ending. In this Wisdom Wednesday episode, MEA founder and author Chip Conley joins Derek Gehl for a deeply personal conversation about facing all three. Drawing on his upcoming book, The Art of the Reframe, Chip shares how he’s finding a way forward without pretending the pain isn’t real. You’ll discover how to: Feel the grief before trying to find the silver lining.Separate what happened from the story you tell yourself about it.Rethink the belief that a marriage ending means it failed.Find new possibilities through a simple reframing practice.Build deeper friendships by opening up about what’s really going on. Watch for an honest conversation about loss, love, and changing your perspective when you can’t change your circumstances. Timestamps: (00:00) The Art of the Reframe (01:20) When Life Changes All at Once (04:33) Reframing Without Ignoring Grief (06:02) Letting Yourself Feel (07:24) Understanding Your Frame (10:44) Rethinking Love and Connection (15:21) Breaking Free from Feeling Stuck (16:14) Routines, Rituals and New Perspectives (17:58) Deeper Friendships and Honest Conversations (19:04) Men, Vulnerability and Emotional Support (22:54) A Simple Reframing Practice (26:02) Psychedelics and Changing Perspective (27:20) Learning to Let Go Learn more about MEA at ⁠https://www.meawisdom.com/ The Art of the Reframe PRE-SALE: http://meawisdom.com/reframebook #ChipConley #DerekGehl #WisdomWednesday #MidlifeChrysalis #TheArtOfTheReframe #ModernElderAcademy #Reframing #MidlifeTransitions #LifeTransitions #NavigatingGrief #MarriageEnding #EmotionalResilience #FeelingStuck #ToxicPositivity #MaleVulnerability

  3. 5d ago

    He Built the Green Building Movement. Then His Life Fell Apart | David Gottfried

    You can build a successful life and still reach a point where you need to rebuild yourself. In this episode, Chip Conley sits down with David Gottfried, co-founder of the U.S. Green Building Council and pioneer of the green building movement, for a candid conversation about success, loss, and reinvention. David shares how transforming an industry was followed by a deeply personal transformation when his 20-year marriage ended and forced him to rethink who he was. They explore: How green building went from a fringe idea to a global movementWhy hiding parts of ourselves can come at a profound costWhat divorce taught David about vulnerability and letting others inWhy letting go of old identities can open the door to a new lifeWhy regeneration must go beyond our planet to include ourselves David’s lesson from it all is simple: “Truth is oxygen.” Watch the full episode for an honest conversation about success, identity, and finding the courage to become Timestamps: (06:13) From Stanford to Real Estate (10:06) Bringing Solar Into Development (12:00) Founding the U.S. Green Building Council (17:12) Making Green Building Mainstream (20:17) How LEED Took Off (22:05) A Midlife Transformation (26:25) Divorce and a Personal Chrysalis (31:05) What Pain Taught Him (33:45) No More Hiding (35:04) The Dark Night of the Ego (37:05) From Sustainability to Regeneration (43:14) What Gives Him Hope (45:08) Truth Is Oxygen Learn more about MEA at ⁠https://www.meawisdom.com/ #DavidGottfried #ChipConley #MidlifeChrysalis #GreenBuilding #USGBC #LEED #RegenerativeLiving #MidlifeReinvention #PersonalTransformation #LifeAfterDivorce #FindingYourself #Vulnerability #Sustainability #Regeneration #SecondHalfOfLife

  4. Oct 16

    Are You in Love With the Past or Trapped by It? | Juan Pablo Di Pace

    Your first love can stay with you for decades. So can the story you keep telling yourself about it. Actor and filmmaker Juan Pablo Di Pace joins Chip Conley for a personal conversation about love, memory, and the past’s hold on our present. Through his film Before We Forget, he revisits a formative teenage love and explores how a memory can be both something we treasure and a wound we carry. He shares: Why romanticizing the past can keep us from moving forward.How old videotapes brought powerful teenage emotions back to life.What it feels like to watch actors recreate moments from your own life.How unexpected friendships can become a chosen family.Why trusting your passion matters more than other people’s opinions. Watch for an intimate look at first love, creative courage, and the memories that follow us into midlife. Timestamps: (10:08) Meet Juan Pablo Di Pace (10:47) A Life of Travel and Creativity (12:04) From Actor to Filmmaker (14:23) Admission and Finding Your People (18:47) The Story Behind Before We Forget (24:19) Memory and Romanticizing the Past (27:38) Turning Personal Experience Into Film (33:13) Bringing Before We Forget to Audiences (35:31) Playing Jesus and Being Yourself (40:48) Advice to His Younger Self (42:28) Follow Your Passion and Study the Greats (45:26) The MEA Film Fest and New Friendships Learn more about MEA at ⁠https://www.meawisdom.com/ Before We Forget TRAILER: https://beforeweforgetmovie.com/ #JuanPabloDiPace #ChipConley #MidlifeChrysalis #BeforeWeForget #DuinoFilm #FirstLove #UnrequitedLove #LoveAndMemory #Midlife #PersonalStorytelling #AutobiographicalFilm #Filmmaking #ChosenFamily #AdmissionFilm #MEAFilmFest

  5. Oct 14

    MEA Film Fest: Come for the Movies, Stay for the Connections

    Watch a great film, then share dinner with the person who made it. That’s the spirit of the MEA Film Fest, where stories on screen spark conversations and connections in real life. In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to preview the festival and explore a question at its heart: how can movies help us see midlife, aging, and our own possibilities differently? Get a preview of the films, special guests, and festival experience.Discover stories of reinvention that go beyond the midlife crisis.Explore what your reactions to characters reveal about your hopes and fears.Bring those conversations home with a simple movie night exercise. Tune in for films worth watching, people worth meeting Timestamps: (01:02) Chip’s Love of Film (02:50) Inside the MEA Film Fest (04:17) Midlife Crisis on Screen (07:44) How Movies Shape Our View of Aging (10:04) Starting a Film Club (11:20) Films to Watch and Discuss (14:51) What Movie Characters Reveal About You (15:44) Finding Meaning in It’s a Wonderful Life (17:06) Closing Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #MidlifeChrysalis #WisdomWednesday #MEA #MEAFilmFest #Midlife #MidlifeTransformation #Aging #Ageism #Movies #FilmClub #Reinvention #PersonalGrowth #MeaningfulConnections #SecondAct

  6. Oct 12

    From Nike CEO to Starting Over at 65: John Donahoe’s Reinvention

    After decades at the top, John Donahoe found himself starting over at 65. John has led eBay, ServiceNow, and Nike. But some of his most important lessons came from burnout, failure, and the difficult transitions between success and what comes next. In this deeply personal conversation, John shares: Why stepping away at 55 changed the way he saw success and himselfWhat 50 wise elders taught him about vitality, purpose, and agingHow his painful departure from Nike challenged his identity at 65Why adversity can become a source of meaning and growthHow an unexpected opportunity at Stanford became his next chapter This is a powerful conversation about starting again, letting go of outcomes, and finding purpose beyond achievement. Watch the full episode with John Donahoe. Timestamps: (03:16) Reinventing Life After 50 (05:07) Burnout and Taking a Year Off (07:56) The Retreat That Changed Everything (10:21) Leaving the Gladiator Ring (13:59) The Search for Vitality (16:12) Lessons From 50 Wise Elders (20:15) Service, Purpose and Serendipity (23:24) The Road to Nike (28:04) Crisis and Failure at Nike (33:15) Lessons From Failure (37:26) A New Chapter at Stanford (41:09) Finding Purpose Again (44:15) The Gift of Adversity (47:33) Turning Pain Into Wisdom Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate Learn more about MEA at ⁠https://www.meawisdom.com/ #JohnDonahoe #NikeCEO #LifeAfterNike #StartingOverAt65 #MidlifeReinvention #WisdomJourney #LeadershipLessons #CareerReinvention #SecondAct #FindingPurpose #Adversity #LifeTransitions #StanfordAthletics #PurposeAfterSuccess #MidlifeChrysalis

  7. Oct 9

    When the Life You Built Is No Longer Enough | Caroline Myss

    Midlife can feel like the life you built suddenly stops fitting. Caroline Myss believes there’s a deeper reason: this is when the soul begins asking something different of you. In this powerful conversation, bestselling author and spiritual teacher Caroline Myss joins Chip Conley to explore the deeper meaning of midlife, purpose, identity, and surrender. Caroline shares: Why a crisis of purpose may actually be a crisis of the soulHow we move from job to career to callingWhy we lose our appetite for the life we’ve builtHow sacred contracts shape our relationships and challengesWhy surrender means releasing fear and control Chip also opens up about his near-death experience and changing identity as Caroline challenges him to see his life through a different lens. Watch the full conversation for a profound look at what happens when the life that once fit you is no longer enough. Timestamps: (3:36) Midlife and the Search for Wisdom (9:15) The Rise of the Inner Self (13:56) When a Crisis Is Spiritual (14:40) What Is Wisdom? (15:30) Sacred Contracts and the Power of Choice (20:45) The People We’re Meant to Meet (23:55) How to Recognize a Sacred Contract (27:16) From Job to Career to Calling (31:00) Why Midlife Changes Us (36:25) Chip’s Near-Death Experience (38:30) Wounds, Identity, and Illness (44:24) Learning to Surrender (47:12) Carolyn’s Hard-Won Wisdom (48:02) God Is Law Learn more about MEA at ⁠https://www.meawisdom.com/ #CarolineMyss #ChipConley #Midlife #MidlifeWisdom #MidlifeCrisis #SpiritualAwakening #SpiritualGrowth #SacredContracts #FindingPurpose #LifePurpose #PersonalTransformation #FindingYourCalling #SoulPurpose #Wisdom #Surrender

  8. Oct 7

    What If the Life You Built Isn’t the Life You Want?

    You’ve built a life that looks successful. Yet the things you worked so hard for may no longer be what you want next. In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to explore finding purpose when familiar roles no longer feel fulfilling. From a corporate lawyer investing in her community to former business owners pursuing screenwriting, Chip shares how people are discovering possibilities they had quietly put aside. You’ll hear: How to recognize someone else’s success script and begin defining success for yourself.Four pathways to purpose: what excites you, agitates you, makes you curious, or feels neglected.Why smaller purposes matter, from learning guitar to making more time for your children.A question to clarify your priorities: what will you regret not learning or doing 10 years from now?A simple exercise to find direction through the moments when you feel useful and lose track of time. Watch the full episode for a thoughtful look at what deserves your time now and what you’d love to make room for next. Timestamps: (00:00) Introduction (00:37) The myth of one purpose (01:41) Why purpose matters in midlife (03:36) Passion, purpose and ikigai (04:40) Four pathways to purpose (05:39) The MEA Purpose Fellowship (08:30) Creating a purpose portfolio (09:40) Finding purpose beyond career success (12:54) Why community helps you find purpose (14:56) Purpose after retirement and an empty nest (17:29) Rethinking relationships (18:25) Chip’s personal purpose portfolio (20:34) Making room for small purposes (21:59) A simple exercise to discover your purpose (23:06) Ways to explore purpose with MEA Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #Purpose #ChipConley #DerekGehl #WisdomWednesday #MidlifeChrysalis #FindingPurpose #LifePurpose #MidlifeTransition #PersonalGrowth #MeaningfulLife #RedefiningSuccess #LifeAfter50 #SelfDiscovery #MEA

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Trailer

4.9
out of 5
82 Ratings

About

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.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    177
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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