EducationSelf-Improvement

The Midlife Chrysalis

Chip Conley

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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48 episodes
a few times a week
Avg 39 min
English

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S1 · E182
Friday · 51 min
Your Turn: How to Create a Midlife You Love with Allison Aubrey
You’ve spent years building a career, caring for others, and doing what’s expected. Midlife is your chance to ask: Who am I now, and what do I want next? NPR health and science journalist Allison Aubrey joins Chip Conley to explore how to create a midlife you love. Drawing on her book, Your Turn, she shares practical ways to find more joy, care for your health, and decide what comes next. You’ll learn: How to reinvent yourself without starting over Why slowing down helps you hear what you really want How to rethink retirement around what you enjoy How the Brain Care Score can guide healthier habits Why finding purpose doesn’t require a big life change Watch the full conversation for a fresh look at midlife and the possibilities ahead. Timestamps: (06:44) Meet Allison Aubrey (08:30) Food as Medicine (09:36) The Value of Midlife Wisdom (11:19) Creating a Midlife You Love (14:04) The Kentucky Derby Midlife Metaphor (19:07) Reinventing Yourself Through Play (24:34) Finding the Courage to Change (26:47) Allison’s Career Transition (30:00) Menopause and Changing Priorities (33:15) Rethinking Retirement (37:36) The Brain Care Score (42:46) Finding Purpose in Everyday Life (47:37) Rediscovering Your Joyful Self Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #AllisonAubrey #ChipConley #YourTurn #MidlifeChrysalis #MidlifeReinvention #LifeAfter50 #HealthyAging #FindingPurpose #SelfDiscovery #BrainHealth #Menopause #RethinkingRetirement #PersonalGrowth #MidlifeTransitions
S1 · E181
Wednesday · 21 min
AI Can Save You Time. Is It Costing You Your Creativity?
AI can save you hours. But are you handing over more than your workload? In this Wisdom Wednesday episode of the Midlife Chrysalis podcast, Chip Conley and Derek Gehl explore how to use AI without losing your voice, creativity, or judgment. Together, they discuss: How they use AI to save time on research and everyday work Why polished writing can lose the personality that makes it yours How outsourcing your thinking can mean missing opportunities to learn What makes your skills and experience valuable in the AI era A simple experiment to decide which tasks to keep doing yourself Watch the full episode to discover where AI can help and where your human experience matters most. Timestamps: (00:00) Introduction (01:12) Will AI Change Everything? (04:19) Use AI Without Letting It Think for You (06:28) How Chip Uses AI to Save Time (10:24) Is AI Making Us Less Creative? (12:43) Why Human Content Still Matters (14:19) What AI Misses About Human Wisdom (16:01) Finding Your Place in an AI World (19:44) Why Human Connection Will Matter More (20:49) What You Should Never Outsource to AI Learn more about MEA at ⁠https://www.meawisdom.com/ #AI #ArtificialIntelligence #HumanConnection #FutureOfWork #CriticalThinking #HumanCreativity #AIProductivity #Midlife #ChipConley #WisdomWednesday #HumanWisdom #Authenticity #CareerReinvention #LifelongLearning #MidlifeChrysalis
S1 · E180
November 2 · 47 min
You Have a Book in You. Here’s How to Finally Write It | Kelly Notaras
That book you’ve been meaning to write isn’t going to write itself. And according to publishing expert Kelly Notaras, you don’t need a perfect plan, a polished first chapter, or even a publisher to get started. Kelly, founder of KN Literary Arts and author of The Book You Were Born to Write, has helped nearly 3,000 authors bring their ideas to the page. In this conversation, she shares what decades in publishing have taught her about writing, creativity, and getting a book into the world. In this episode, Kelly shares: Why midlife can be a powerful time to finally write the book you’ve been carrying The three things publishers are looking for from authors today Why self publishing is no longer Plan B and can actually open doors to traditional publishing How perfectionism keeps writers stuck and why the first draft needs to be messy Why finding the right time, space, and people to write with can transform your creative process If there’s a book you keep telling yourself you’ll write someday, this conversation is a great place to start. Watch the full episode and discover how to stop waiting and start writing. Timestamps: (03:54) Kelly’s Journey Into Publishing (06:45) Leaving Traditional Publishing (10:42) Working With 3,000 Authors (13:44) What Publishers Look for Today (19:31) Traditional vs. Self-Publishing (23:25) The Best Way to Self-Publish (24:34) Why Midlife Is the Perfect Time to Write (29:00) How to Create Your Best Writing (32:30) Inside a Writing Retreat (36:08) Turning Life Experience Into a Book (39:11) The Most Important Lesson Kelly Learned (39:49) Don’t Just Do Something, Sit There Learn more about MEA at ⁠https://www.meawisdom.com/ #WritingABook #MidlifeWriting #BookWriting #WritingTips #AspiringAuthors #SelfPublishing #PublishingTips #CreativeWriting #WritingInMidlife #BookPublishing #KellyNotaras #KNLiteraryArts #MidlifeCreativity #FirstDraft #MidlifeChrysalis
S1 · E179
October 30 · 50 min
Stop Chasing Happiness: Find Joy in the Life You Have | Mark Coleman & Lori Schwanbeck
You can spend years chasing happiness and miss the life happening right in front of you. In this episode of The Midlife Chrysalis, Chip Conley joins mindfulness teachers Mark Coleman and Lori Schwanbeck to explore how to feel more present, connected, and fully alive in midlife. Together, they explore: How changing what you pay attention to can change your experience of life Why nature makes mindfulness easier and teaches us to let go How gratitude helps you appreciate your life, even when things are hard Why midlife’s losses and transitions can open the door to new possibilities How to quiet your inner critic and recognize your own worth Watch the full episode for simple ways to step out of your head, reconnect with the world around you, and find more joy in the life you have. Timestamps: (06:27) Meet Mark and Lori (07:23) Lori’s Path to Mindfulness (10:34) From Punk Rock to Meditation (13:03) Finding Peace in the Present (15:42) How to Reframe Your Thoughts (17:40) Mindfulness in a Distracted World (19:53) Why Nature Helps Us Slow Down (23:36) Making Meditation Easier Outdoors (26:10) Why Midlife Sparks Inner Change (29:53) Facing Mortality and Loss (33:51) Psychedelics and New Possibilities (37:13) Gratitude and Nature in Baja (39:43) Making Gratitude a Daily Practice (41:34) Gratitude Versus Gratification (43:06) Remembering to Fully Live (45:27) Making Peace with Your Inner Critic Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #ChipConley #MarkColeman #LoriSchwanbeck #Mindfulness #Midlife #MidlifeTransition #NatureMeditation #Gratitude #MindfulLiving #LettingGo #SelfCompassion #InnerCritic #PersonalGrowth #FindingJoy
S1 · E178
October 28 · 15 min
Dreading the Holidays? Create Traditions You Actually Enjoy
The kids have moved out. Family gatherings feel complicated. Suddenly, the holidays you used to love leave you wondering where you belong. In this Wisdom Wednesday episode, MEA founder Chip Conley joins host Derek Gehl to explore why holidays change in midlife and how new traditions can bring back a sense of connection. Discover how to: Build celebrations around people you genuinely want to spend time with. Embrace Friendsgiving without the guilt of breaking with tradition. Find friendship and a fresh start through a holiday retreat. Plan a meaningful gathering without taking on all the work. Watch now for inspiration to make this holiday season feel more connected, more joyful, and more your own. Timestamps: (00:00) Introduction (01:44) How Holidays Change in Midlife (02:14) Loneliness and Chosen Family (06:14) Choosing Friendsgiving Over Family Drama (07:20) Creating a New Year’s Tradition (08:46) Holiday Retreats in Santa Fe and Baja (11:05) Finding Connection During the Holidays (12:03) Choosing Your Friendsgiving Guests (12:41) Planning Ahead for the Holidays (14:25) Making Holiday Gatherings Easier (15:30) Upcoming Thanksgiving Workshops Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #Holidays #Friendsgiving #ChosenFamily #HolidayLoneliness #NewTraditions #ChipConley #MidlifeChrysalis #HolidayStress #Connection #Thanksgiving #FamilyDynamics #HolidayRetreats #MeaningfulHolidays #MEA
S1 · E177
October 26 · 43 min
How to Lead with Heart and Still Make Tough Calls | John Baird
The hardest conversations are often the ones that help us grow. John Baird has spent 30 years coaching leaders at Apple. At 82, he’s still coaching, trying new things, and making time for what matters most. In this episode of The Midlife Chrysalis, John joins Chip Conley for a warm, candid conversation about leading with heart, making tough decisions, and building a meaningful life. He shares: How to hold people accountable while treating them with care. Why strong teams say the things everyone is thinking. How to turn your experience into a coaching career in midlife. Why revisiting your priorities matters in both work and marriage. How curiosity and gratitude keep life rich at any age. Watch for practical wisdom on becoming a better leader and making more room for the people who matter to you. Timestamps: (02:31) Meet John Baird (03:25) Rethinking Work, Marriage, and Family (05:53) Coaching Leaders at Apple (09:50) Steve Jobs’ Leadership After His Return (11:26) Honest Feedback and Stronger Teams (13:11) Leading with Heart and Toughness (14:10) Seven Habits of Tough Leadership (19:09) Helping Intel Navigate Change (20:38) Finding Purpose at 82 (23:36) Becoming a Coach in Midlife (27:55) Measuring Coaching Results (29:59) Do You Need Coaching Credentials? (31:36) Questions That Turn Insight into Action (34:22) Curiosity, Gratitude, and Difficult Conversations Learn more about MEA at ⁠https://www.meawisdom.com/ #JohnBaird #ChipConley #MidlifeChrysalis #Leadership #ExecutiveCoaching #LeadingWithHeart #ToughEnough #DifficultConversations #EmpatheticLeadership #SteveJobs #AppleLeadership #MidlifeReinvention #PurposefulLiving #PersonalGrowth #LifelongLearning
S1 · E176
October 23 · 47 min
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
S1 · E175
October 21 · 27 min
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
S1 · E174
October 19 · 48 min
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 movement Why hiding parts of ourselves can come at a profound cost What divorce taught David about vulnerability and letting others in Why letting go of old identities can open the door to a new life Why 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
S1 · E173
October 16 · 43 min
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
S1 · E172
October 14 · 17 min
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
S1 · E171
October 12 · 51 min
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 himself What 50 wise elders taught him about vitality, purpose, and aging How his painful departure from Nike challenged his identity at 65 Why adversity can become a source of meaning and growth How 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
S1 · E170
October 9 · 54 min
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 soul How we move from job to career to calling Why we lose our appetite for the life we’ve built How sacred contracts shape our relationships and challenges Why 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
S1 · E169
October 7 · 23 min
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
S1 · E168
October 5 · 44 min
He Died 11 Years Ago. Their Relationship Never Ended. | Lucy Kalanithi
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 love How grief changes over time, even when the love remains Why caregivers need permission to ask for help and protect themselves How losing Paul changed the way she cares for patients and their families How 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
S1 · E167
October 2 · 35 min
Why Life Can Get Harder and Happier After 50 | Jonathan Rauch
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 expect Why life satisfaction often rises after 50, even through setbacks Why young adults’ loss of hope concerns Rauch Why free speech alone is not enough to establish what is true How 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
S1 · E167
September 30 · 27 min
The Hardest Leadership Lesson: Let Someone Else Be the Hero
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 back How asking questions helps others grow into leaders Why purpose matters as an organization gets bigger How to build something that can thrive without you What 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
S1 · E165
September 28 · 35 min
What Changes When You Finally Let Go of Control? | Thomas DeLong
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 relationships How to move from image management to essence Why vulnerability is a powerful form of courage How inherited success scripts can define the path we follow Why 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
S1 · E164
September 25 · 51 min
Let Life Lead: A Different Way to Navigate Midlife | Nic Askew
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 cannot How stillness creates space for the soul rather than the ego to lead Why doing less can help us truly see and connect with others How 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
S1 · E163
September 23 · 24 min
Be Useful, Not Youthful: The Secret to Aging Well
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 irrelevant How to move from “sage on the stage” to “guide on the side” Why being useful matters more than staying youthful How becoming “good soil” helps other people and future generations flourish Why 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

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