Advertise on podcast: The Midlife Chrysalis

“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

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

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

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

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

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

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

Eleven years after losing her husband, the pain has changed. The love hasn’t. Dr. Lucy Kalanithi, physician and widow of Paul Kalanithi, author of When Breath Becomes Air, joins Chip Conley for a deeply personal conversation about grief, caregiving, uncertainty, and building a meaningful life after profound loss. Drawing on her experience as a wife, mother, caregiver, and doctor, Lucy shares what more than a decade of living with grief has taught her: Why death doesn’t necessarily end our relationship with someone we loveHow grief changes over time, even when the love remainsWhy caregivers need permission to ask for help and protect themselvesHow losing Paul changed the way she cares for patients and their familiesHow to live with uncertainty when there are no clear answers Watch the full episode for a moving perspective on love, loss, and what it means to keep living when life changes forever. Timestamps: (04:14) Lucy Kalanithi’s Story (05:20) When Breath Becomes Air (06:40) Staying Connected After Loss (13:20) How Grief Changes Over Time (14:18) Advice for Living With Grief (16:04) How Loss Changed Her as a Doctor (18:44) The Reality of Caregiving (21:06) What Caregivers Really Need (23:45) Living With Uncertainty (27:33) Finding Acceptance in the Unknown (31:42) Serenity, Courage, and Wisdom (35:05) Raising a Child After Loss (38:13) Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ Be part of the conversation at the End Well Conference in Los Angeles on November 12, where Lucy Kalanithi and Chip Conley will take the stage to explore how we can live, care, and face life’s biggest transitions with greater meaning. Learn more and get tickets: https://endwellproject.org/end-well-2026/ #LucyKalanithi #PaulKalanithi #WhenBreathBecomesAir #Grief #LifeAfterLoss #LoveAfterLoss #Bereavement #Caregiving #LivingWithLoss #Mortality #Uncertainty #Acceptance #MidlifeWisdom #ChipConley #MidlifeChrysalis

Jonathan Rauch had reached the top of his career, yet each year he felt less satisfied. Then came the loss of his parents, his job, and a startup he had tried to build. To his surprise, his sense of contentment began to grow. Rauch is a journalist and the author of The Happiness Curve, The Constitution of Knowledge, and Cross Purposes. He joins Chip Conley to explore what his personal experience and research reveal about getting older, and why the future looks more troubling for younger adults. In this conversation: Why achievement does not always bring the happiness we expectWhy life satisfaction often rises after 50, even through setbacksWhy young adults’ loss of hope concerns RauchWhy free speech alone is not enough to establish what is trueHow wisdom helps us navigate conflict, and why it can be taught Watch for an honest, thought-provoking conversation about happiness, truth, and the value of staying curious throughout life. Timestamps: 03:49 Seeing what others miss06:59 The midlife happiness curve10:31 Why life can get better after 5012:21 Why young adults are losing hope15:49 How society knows what is true20:57 Wisdom in an age of disinformation24:53 Advice for the next generation26:34 Staying curious as we age Learn more about MEA at ⁠https://www.meawisdom.com/ #JonathanRauch #ChipConley #TheHappinessCurve #HappinessAfter50 #MidlifeHappiness #AgingWell #LifeSatisfaction #YoungAdultHappiness #Wisdom #Truth #Disinformation #ConstitutionOfKnowledge #ModernElder #MidlifeWisdom #Curiosity

Being the person who saves the day feels good. But letting someone else do it can make you a better leader. MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach. Chip shares how he is learning to step back, trust his team, and make room for others to lead. Why having all the answers can hold your team backHow asking questions helps others grow into leadersWhy purpose matters as an organization gets biggerHow to build something that can thrive without youWhat leadership can become in your next chapter Watch the full episode to hear Chip’s candid take on letting go and leading with greater wisdom. Timestamps: (00:00) Intro (02:30) From Hero to Coach (04:39) Bill George and Purpose Driven Leadership (07:40) Learning to Lead Together (10:06) Servant Leadership (11:20) Finding Meaning in Work (12:31) Leadership as a Practice (14:19) Building Culture Across an Organization (16:09) Building an Organization That Thrives Without You (18:25) Your Next Chapter of Leadership (22:48) The Bill George Workshop (25:17) A Leadership Experiment Learn more about MEA at ⁠https://www.meawisdom.com/ Listen to the podcast episode with Bill George, CEO of Medtronic: https://youtu.be/M9PuSyubTB0 #ChipConley #Leadership #LeadershipDevelopment #WiseLeadership #MidlifeLeadership #ServantLeadership #FounderLeadership #LeadershipCoaching #Mentorship #PurposeDrivenLeadership #OrganizationalCulture #BillGeorge #ModernElder #WisdomWednesdays #TeamLeadership

Success can look impressive on a résumé and still leave you wondering who you really are. At 76, Harvard Business School professor and former Morgan Stanley executive Thomas DeLong is rethinking some of the biggest lessons he has learned about leadership, courage, relationships, and success. In this conversation with Chip Conley, he reflects on: Why letting go of control can deepen relationshipsHow to move from image management to essenceWhy vulnerability is a powerful form of courageHow inherited success scripts can define the path we followWhy later life is about investing wisdom, not just retiring From family and leadership to identity and aging, DeLong shares the hard-earned lessons that have changed how he sees himself and the people around him. Watch now for a deeply personal conversation about letting go, finding courage, and defining success on your own terms. Timestamps: (02:40) Letting Go of Control (04:31) Building Closer Relationships (07:20) Vulnerability With His Daughters (09:35) Courage and Self-Doubt (13:00) Courageous Life Decisions (16:45) From Image to Essence (20:44) Changing Leadership at Morgan Stanley (23:38) The Parable of the Sadhu (26:04) Measuring a Meaningful Life (30:58) Investing Wisdom in the Next Decade (34:00) Sing Loudly and in Harmony (36:10) Breaking Free From the Success Script (38:36) A New Definition of Success Learn more about MEA at ⁠https://www.meawisdom.com/ Watch Chip’s Soul Biography, created by filmmaker Nic Askew: MEAWisdom.com/Soul #ThomasDeLong #ChipConley #MidlifeChrysalis #HarvardBusinessSchool #Leadership #RedefiningSuccess #PersonalGrowth #SelfAcceptance #Vulnerability #Courage #LettingGo #MidlifeWisdom #AuthenticLeadership #LifeLessons #HealthyAging

Sometimes the most powerful way forward begins by doing less. Filmmaker Nic Askew has spent more than two decades capturing what happens when people stop performing and simply allow themselves to be seen. Through his Soul Biographies, he has discovered a different way of approaching connection, identity, and life itself. In this episode, Nic explores: Why “starting with nothing” can reveal what effort cannotHow stillness creates space for the soul rather than the ego to leadWhy doing less can help us truly see and connect with othersHow letting go of control can reveal what comes next in lifeIt’s a fascinating conversation about soul, human connection, and learning to let life lead. Watch the full episode and discover the power of starting with nothing.  Timestamps: (03:24) Discovering Filmmaking at Midlife (04:18) Picking Up a Camera (08:54) A Calling Out of Nowhere (12:14) Starting With Nothing (16:53) The Soul Biographies (17:32) Speaking From Ego vs. Soul (19:17) Letting Life Lead (23:48) Stillness Before Action (28:13) Truly Seeing Others (31:07) Deepening Connection (37:34) Filming the MEA Community (42:13) Seeing Beyond the Persona (46:51) Nic’s Life Wisdom  The Soul of MEA, the link is: MEAWisdom.com/Soul Learn more about MEA at ⁠https://www.meawisdom.com/ #NicAskew⁠ ⁠#SoulBiographies⁠ ⁠#Midlife⁠ ⁠#MidlifeTransformation⁠ ⁠#PersonalGrowth⁠ ⁠#SelfDiscovery⁠ ⁠#AuthenticLiving⁠ ⁠#LifePurpose⁠ ⁠#HumanConnection⁠ ⁠#Stillness⁠ ⁠#SoulWork⁠ ⁠#MidlifeWisdom⁠ ⁠#LetLifeLead⁠ ⁠#Presence⁠ ⁠#MEA

At some point in midlife, achievement stops being enough. The titles matter less, the phone may stop ringing, and the question becomes: where does your value come from now? In this episode of Wisdom Wednesday, MEA founder Chip Conley joins Derek Gehl to explore the shift from achievement and admiration toward generativity, usefulness, and helping others grow. Key insights include: Why feeling invisible doesn’t mean becoming irrelevantHow to move from “sage on the stage” to “guide on the side”Why being useful matters more than staying youthfulHow becoming “good soil” helps other people and future generations flourishWhy doing good without getting credit can be one of the most meaningful forms of contribution Watch the full episode to discover a different way to think about purpose, relevance, and growing older. Timestamps: (00:00) Welcome to Wisdom Wednesday (00:41) The Sacred Pause (03:48) Becoming Good Soil (05:43) Regenerating Soil and Soul (07:55) Shifting Roles in Midlife (08:30) From Sage to Guide (10:21) Generativity vs. Stagnation (13:47) Staying Generative After Retirement (15:20) Feeling Invisible in Midlife (15:59) What You Have to Offer (18:55) Be Useful, Not Youthful (19:15) Finding a New Role (21:19) Crystallized Intelligence (22:26) Give Without Getting Credit (23:55) Letting Others Grow (25:12) Quiet Generosity 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/ #ChipConley #MidlifeChrysalis #ModernElderAcademy #WisdomWednesday #Generativity #MidlifePurpose #LifeAfter50 #AgingWell #MidlifeWisdom #CrystallizedIntelligence #PurposeAfter50 #Mentorship #MidlifeTransition #SacredPause #GoodSoil

We’re taught to expect decline as we get older. But the science tells a far more hopeful story. In this episode, bestselling author and positive psychology expert Shawn Achor joins us to explore how our beliefs can shape the way we age. Drawing from his new book, The Power of Beliefs, groundbreaking research, and his own midlife experience, Shawn reveals why getting older can bring new opportunities for growth, meaning, happiness, and wisdom. You’ll discover: How beliefs about aging can influence our physical and cognitive outcomesWhy midlife doesn’t have to mark the beginning of declineHow negative expectations can become powerful nocebo effectsWhy life can become more meaningful even as our priorities changeHow “neuroscaping” can reshape the stories we tell about our lives From stepping away from career success to rediscovering what truly matters, Shawn offers a compelling new perspective on aging and the potential that remains ahead. Watch now to discover why your beliefs about getting older may matter more than you think. Timestamps: (03:04) Finding Joy and Wonder in Family Life (04:54) Rethinking Potential in Midlife (09:07) How Fatherhood Changed His Priorities (12:47) Feeling Replaced and Rediscovering Meaning (15:20) How Divinity School Reshaped His Faith (20:16) The Power of Beliefs (24:18) The Nocebo Effect (25:38) How Beliefs About Aging Shape Outcomes (29:09) Optimism and the U-Curve of Happiness (34:11) Why Meaning Can Grow With Age (38:51) Neuroscaping Your Memories (45:59) Turning Possibility Into Reality (47:21) Why Happiness Leads to Success (50:58) Growing Wiser With Age Learn more about MEA at ⁠https://www.meawisdom.com/ #ShawnAchor #PositivePsychology #PowerOfBeliefs #Midlife #HealthyAging #PsychologyOfAging #Happiness #Mindset #AgingWell #PersonalGrowth #MeaningAndPurpose #Optimism #Neuroscaping #MidlifeGrowth #SuccessfulAging

What can the world’s oldest people teach us about time, aging, and being alive? Academy Award nominated filmmaker Sam Green spent 10 years filming people who held the title of the world’s oldest living person. His documentary The Oldest Person in the World began as a curiosity but became a deeply personal exploration of mortality, connection, and how we use the time we have. In this episode, Sam shares: What life really looks like at 115 and what seems to matter mostThe surprising traits he noticed among the world’s oldest peopleHow a serious illness transformed his own relationship with timeWhy accepting life’s uncertainty can change how we liveHis advice for staying connected, creative, and engaged as we age This conversation isn’t about defeating aging. It’s about paying attention to the life you have while you have it. Watch now for a fascinating perspective on longevity, mortality, and what makes a life meaningful. Timestamps: (05:13) The Oldest Person in the World (08:14) Longevity vs. Mortality (10:21) What Centenarians Have in Common (13:20) What Life Is Like at 115 (15:12) Meeting the World’s Oldest People (17:49) What Helps Us Live Longer (19:36) A Life-Changing Diagnosis (23:22) The Film Distribution Challenge (28:02) Making a Living in Documentary Film (30:19) Becoming a Filmmaker (32:33) Advice for Aspiring Filmmakers (36:01) Favorite Documentaries (38:07) Would You Live to 115? (39:50) The Origins of MEA (42:14) Make Younger Friends 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/ #SamGreen #TheOldestPersonInTheWorld #Longevity #Aging #HealthyAging #Mortality #LivingTo115 #DocumentaryFilm #DocumentaryFilmmaking #Midlife #LifeLessons #MeaningfulLife #SundanceFilmFestival #Wisdom #MEA