

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.
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.
Episodes
Mentioned books

Oct 27, 2025 • 1h 3min
BJ Miller: How Facing Death Taught Me to Live More Fully
What if the worst thing that ever happened to you became the very thing that set you free? 🌱 In this deeply moving episode, Dr. BJ Miller—physician, amputee, and palliative care visionary—shares how a near-fatal accident in college transformed his understanding of life, loss, and what it really means to live fully. From his journey through unimaginable pain to founding Mettle Health, BJ reveals how facing mortality can open the door to compassion, creativity, and peace.If you’ve ever feared aging, grief, or change, this conversation will completely shift your perspective.👉 Watch now and discover how to turn life’s hardest moments into your greatest teachers. Timestamps:00:00 Introduction00:36 The Accident That Changed Everything04:17 Processing Grief and Feeling “Seen”09:27 Rebuilding Life in His 20s14:46 From Art History to Medicine16:24 Discovering Palliative Care20:27 What Palliative Care Really Means24:26 Spiritual Dimensions of Caregiving27:16 What We Get Wrong About Death29:42 Making All Healthcare Palliative32:44 Founding Mettle Health36:56 Advice for Caregivers41:25 The Power of Grief43:50 BJ’s Midlife Chrysalis47:49 What People Regret Most Before Death51:48 Dying as a Creative Act55:25 Wisdom Bumper StickerLearn more about MEA at https://www.meawisdom.com/#BJMIller #MidlifeChrysalis #ChipConley #EndOfLifeCare #PalliativeCare #HospiceCare #GriefAndHealing #MidlifeWisdom #CaregivingJourney #FindingMeaning #LifeAndDeath #SpiritualGrowth #EmotionalResilience #MindfulLiving #AuthenticLife

Oct 22, 2025 • 1h
Daniel Pink: The Power of Regret and the Freedom to Begin Again
In this conversation with Daniel Pink, a bestselling author renowned for his works on motivation and timing, listeners discover the power of regret as a guide in life. Pink shares his insights on midlife as a creative turning point, emphasizing the importance of autonomy, mastery, and purpose over mere paychecks. He discusses the joy and challenge of becoming a beginner again after 50, his year-long sabbatical, and the value of reimagining retirement into a regenerative phase. His reflections highlight the wisdom gained through aging and the importance of living authentically.

Oct 15, 2025 • 50min
Love, Loss & Caregiving with Bruce Willis’ Wife, Emma Heming Willis
What happens when the person you love most slowly begins to disappear before your eyes? In this deeply emotional and inspiring conversation, Emma Heming Willis opens up about life with Bruce Willis following his diagnosis of frontotemporal dementia and how she turned heartbreak into purpose. Joined by Helen Christoni, co-founder of Make Time Wellness, the two reveal why women’s brain health is so often ignored, what every caregiver needs to hear, and how to rediscover joy even in the hardest seasons of life.👉 Watch now and learn how making time for yourself might just be the most powerful act of care there is. Timestamps:00:00 Intro00:54 How Helen and Emma created Make Time Wellness04:47 Hormones, estrogen loss, and dementia risk06:03 Helen’s personal connection to dementia08:04 Starting Make Time as Bruce’s symptoms appeared08:51 How Emma met Bruce Willis and first signs of FTD12:05 Understanding anosognosia and early dementia signs15:29 The meaning of ambiguous loss for caregivers18:45 Practical tools and exercises for caregivers20:37 Redefining self-care and “making time”21:20 How others can help caregivers in real ways24:09 The caregiving crisis and policy change needed28:43 Gender roles and men’s perspective on caregiving31:00 Make Time Wellness mission and products34:49 Bruce Willis’s current condition and progression38:20 How their daughters are coping and family life39:24 Emma’s and Helen’s advice for caregivers40:57 Wisdom bumper sticker44:57 Closing reflections and gratitude Learn more about MEA at https://www.meawisdom.com/#EmmaHemingWillis #HelenChristoni #MidlifeCaregiving #WomensBrainHealth #CaregiverSupport #FrontotemporalDementia #DementiaAwareness #MakeTimeWellness #MidlifeResilience #SelfCareReimagined #MidlifeWisdom #WomenSupportingWomen #CaregivingJourney #FindingJoyAgain #ModernElderAcademy

Oct 8, 2025 • 1h 11min
Arthur Brooks on How to Break Free from the Striver’s Curse in Midlife
What if everything you’ve been taught about happiness and success is upside down?In this episode of Midlife Chrysalis, Chip Conley talks with Arthur Brooks, Harvard professor, bestselling author, and former French horn prodigy, about his remarkable journey from the concert stage to the world of behavioral science. Together, they unpack why strivers burn out, how our brains shift from fluid to crystallized intelligence, and the simple formula that can turn midlife from a crisis into a transformation.Don’t miss this inspiring conversation. Listen now and start rethinking your own second curve. Timestamps:00:00 Intro01:06 Arthur Brooks’ origins and family background02:59 Religious upbringing and conversion to Catholicism04:56 Navigating academia and faith in secular environments07:08 Early music training and struggles to become the best13:06 Striver mentality and American entrepreneurship DNA16:41 Leaving music for economics and behavioral science20:52 Imposter syndrome and skills learned from performance22:33 Becoming CEO of the American Enterprise Institute (AEI)29:05 Burnout, midlife shift, and vital plane encounter 32:19 Plane encounter with a famous figure and reflection on decline35:47 Realizing the need for a second curve38:10 How we move from fluid to crystallized intelligence42:43 Airbnb and the role of “modern elder” wisdom45:02 Advice for shifting into careers built on crystallized intelligence46:56 The danger of pride and Dante’s frozen Satan metaphor49:40 Learning to want less: the secret to second-curve happiness54:39 Editing life instead of accumulating - reverse bucket lists55:55 Generativity, religion, and aging with meaning57:16 Policy thoughts on midlife education and wisdom schools1:01:59 Wisdom bumper sticker1:05:28 Closing reflections from Chip Learn more about MEA at https://www.meawisdom.com/

Oct 1, 2025 • 60min
From Near Death to Super Age: David Stewart’s Bold Reboot
What happens when a world-famous photographer nearly loses everything — and turns it into a movement redefining aging?In this powerful conversation, David Stewart shares his journey from shooting Vogue covers and working with Andy Warhol’s circle, to battling a life-threatening autoimmune disease that forced him to rethink everything. Out of crisis came transformation — and the creation of Ageist and Super Age, two platforms challenging stereotypes about aging and proving that purpose, health, and vitality don’t fade with time.Watch now to discover how to stay healthier, live longer, and embrace your true greatness.Timestamps:00:00 Catching up: Manhattan, travel, and life during Covid01:36 Childhood, school struggles, and proving people wrong04:07 Studying engineering, switching to political science, and discovering photography06:14 Declaring himself a photographer, early Vogue ad, and move to Paris07:01 Life in New York: Andy Warhol’s scene, magazine covers, and big clients08:02 Health crisis, autoimmune disease, and a year in hospital10:00 Turning point: removing his spleen and changing lifestyle11:01 The birth of Ageist: challenging age stereotypes in media and advertising14:50 White-light moment with AT&T campaign and marketing blind spots18:50 Age dysmorphia, beauty industry challenges, and why older audiences are complex21:27 From Ageist to Super Age: growth, readership, and global impact25:27 Health transformation and connecting mindset with the body30:00 Teaching moments: embodied wisdom, confidence, and breaking limits33:55 What Super Age does: informing, inspiring, and offering trusted tools35:10 Longevity pillars: sleep, fitness, stress management, and community37:31 Why grip strength and VO₂ max matter for longevity41:42 Smart habits vs. fads: avoiding “dumb stuff” and focusing on basics44:39 Managing stress, hormetic adaptation, and resilience45:00 Why men chase longevity more than women46:04 Thoughts on Brian Johnson and longevity biohacking47:50 The future of health: AI-driven personalized medicine51:28 Wearables: when they help vs. when they hurt53:12 Passing wisdom to the next generation: embracing greatness and usefulness56:15 Final reflections: passion, usefulness, and living as a contenderLearn more about MEA at https://www.meawisdom.com/#Longevity #HealthyAging #RedefiningAging #SuperAge #Ageist #MidlifeReinvention #MindsetMatters #AgingWell #LifeAfterCrisis #HealthTransformation #Vitality #BreakingAgingStereotypes #AgingStrong #LongevityLifestyle #AgelessLiving

Sep 24, 2025 • 42min
Midlife Awakening & Spiritual Growth with Anne Lamott & Neal Allen
What happens when a bestselling writer and a former corporate executive dive deep into life’s second half?In this powerful conversation, Anne Lamott and Neal Allen share raw, funny, and moving stories about midlife transformation, spiritual awakening, recovery, and how to finally silence that relentless inner critic. From faith and writing to intimacy, aging, and finding purpose, their wisdom will leave you inspired — and maybe even rethinking your own path.👉 Don’t miss this chance to hear life-changing insights from two voices who know the journey inside out. Watch now and discover how midlife can become your most powerful chapter yet.Timestamps:00:00 From Corporate Life to Spiritual Coaching06:08 Annie’s Christian Spirituality08:19 Annie’s Childhood, Religion & Humor12:46 Embracing Christianity in a Ghetto Church14:40 Annie’s Left-Wing Christianity Views17:23 Anne’s Washington Post Columns on Aging21:04 Imposter Syndrome & Life After 5024:50 The Value of Intimacy & Deeper Connection28:51 Taming the Inner Critic Workshop33:46 Wisdom Bumper StickersLearn more about MEA at https://www.meawisdom.com/#AnneLamott #NealAllen #MidlifeChrysalis #SpiritualGrowth #LifeAfter50 #InnerCritic #WritingCommunity #RecoveryJourney #ChristianSpirituality #PersonalTransformation #MindfulnessPractice #AgingWisdom #SpiritualCoaching #SelfAwarenessJourney #FaithAndHealing

Sep 17, 2025 • 1h 9min
How to Rewrite Your Story After a Life Quake with Bruce Feiler
What if the most painful disruptions in life—illness, job loss, divorce, or even an empty nest, were actually the keys to growth?Bestselling author Bruce Feiler shares how “life quakes” shake up our stories and push us to rewrite them. From his own battle with cancer and family upheaval to studying hundreds of life transitions, Bruce reveals why resilience is a skill, not a trait, and how rituals, creativity, and storytelling can turn crisis into renewal. Dive into his powerful seven tools for navigating transitions, learn why the myth of the midlife crisis is outdated, and how to finally become the hero of your own story.✨ Tune in to discover how to transform life’s hardest moments into your greatest turning points.Timestamps:00:00 Intro00:40 Introduction to Bruce Feiler02:24 Background, early life & first book07:09 Life quakes and losing control of your story12:15 Knowing when a transition is complete18:11 The three stages of transition24:40 Seven tools for navigating transitions30:31 Acceptance and rituals to mark change35:18 The ritual renaissance & new book preview41:28 Routine vs. ritual explained45:09 Shedding habits & finding creativity49:19 Updating your story & unveiling your new self51:19 The debate: midlife vs. transitions at all ages58:51 Wisdom bumper sticker01:04:22 Closing reflections & gratitudeLearn more about MEA at https://www.meawisdom.com/#BruceFeiler #LifeQuakes #MidlifeTransitions #ReinventYourself #LifeIsInTheTransitions, #PersonalGrowth #OvercomingCrisis #FindingMeaning #ResilienceInMidlife #RewriteYourStory #RitualsAndRenewal #MidlifeReinvention #SelfDiscoveryJourney #ThrivingThroughChange #BeTheHeroOfYourStory

Sep 10, 2025 • 1h 2min
Elizabeth Gilbert’s Untold Story of Love and Addiction
How do you survive when the person you can’t live without begins to destroy you?In this powerful episode of Midlife Chrysalis, Elizabeth Gilbert joins Chip Conley to share the raw story behind her new memoir, All the Way to the River. She opens up about walking alongside her partner through addiction and relapse, confronting her own patterns of codependency, and finding healing through recovery and surrender. It’s an honest, unfiltered look at love, loss, and what it really takes to stand on your own two feet.Tune in now to hear Elizabeth Gilbert as you’ve never heard her before. Timestamps:00:00 Intro00:40 Introduction to Elizabeth Gilbert03:06 All the Way to the River book06:06 Why it took 7 years to write07:21 A forensic look at repeating patterns10:36 Love vs. addiction in relationships13:49 How Liz met Raya & their evolving bond19:55 Confessing love during Raya’s illness25:31 Grief, loss, and missing her friend27:18 Writing in solitude & surrendering to truth35:00 Surrender, recovery, and true powerlessness41:21 Dark thoughts & God’s voice45:15 What sex & love addiction means for Liz51:36 12-step practices & six years of abstinence54:35 Reflections on MEA and retreat power58:22 Wisdom bumper stickerLearn more about MEA at https://www.meawisdom.com/#MidlifeChrysalis #ElizabethGilbert #AllTheWayToTheRiver #GriefJourney #AddictionRecovery #LoveAndLoss #Codependency #HealingFromTrauma #12StepRecovery #SexAndLoveAddiction #SpiritualGrowth #MemoirWriting #MidlifeWisdom #EmotionalSobriety #LifeLessons

Sep 3, 2025 • 1h 2min
From Punk Rock Pastor to Spiritual Outlaw: Rob Bell’s Midlife Reinvention
What happens when one of America’s most celebrated pastors dares to question everything?In this unfiltered conversation, Rob Bell, once dubbed the “punk rock pastor” and author of the explosive bestseller Love Wins, opens up about the controversy that made him Christianity’s most talked-about heretic, why he walked away from his megachurch at the height of fame, and how midlife pushed him to reinvent himself.From faith and psychedelics to wisdom traditions, AI, and the art of living an unpigeonholable life, Rob’s journey is as provocative as it is inspiring. Whether you see him as a rebel, visionary, or outlaw, one thing’s clear: you won’t walk away from this episode thinking the same.Timestamps:00:00 Intro00:35 Meet Rob Bell02:08 Following a Calling & Evolving05:16 Early Life & First Sermons11:04 Starting Mars Hill Church13:02 Performance Art Preaching15:01 Controversy & Pushback16:44 Rise to Time’s 100 Most Influential People21:10 Leaving the Church & Midlife Transition26:25 Reinventing in His 40s29:58 Evolving Faith & Moving Beyond Doctrine31:46 The Greatest Unlearning35:00 Surfing, painting & daily rituals38:15 Reconnecting with Spirituality40:25 On Psychedelics & Temples44:57 From Knowledge to Wisdom51:16 Redefining Intelligence54:56 Rob’s Wisdom Bumper Sticker57:47 Closing ReflectionsChip shares key takeaways on creativity, freedom, and living beyond expectations.Learn more about MEA at https://www.meawisdom.com/#RobBell #MidlifeChrysalis #PunkRockPastor #LoveWins #SpiritualJourney #MidlifeTransitions #FindingPurpose #WisdomTraditions #SpiritualAwakening #FaithAndCreativity #LeavingReligion #SpiritualGrowth #Unpigeonholable #MidlifeSpirituality #CareerEvolution

Aug 27, 2025 • 58min
How Intergenerational Living Creates Purpose & Joy | Marc Freedman
What if aging wasn’t about slowing down—but about leveling up?In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate), unpacks the surprising history of retirement, why communities like Sun City reshaped how we see aging, and how we can flip the script on what it means to grow older. From encore careers to intergenerational mentorship, Marc shows why midlife is no dead end—it’s a launchpad for purpose, impact, and connection.If you’ve ever wondered how to thrive after 50, find meaning in your “second act,” or simply stay relevant in a rapidly changing world, this episode will change how you see the road ahead.Timestamps:00:00 Intro00:39 Marc Freedman as Chip’s “modern elder”02:46 How aging became feared, not revered04:26 Why older people are no longer revered07:30 Rise of retirement communities13:14 Why people question retirement as a goal15:56 Marc’s personal view on retirement18:36 The origins & evolution of CoGenerate24:10 Why intergenerational connection matters27:46 What CoGenerate does to help31:52 Big policy ideas for the future37:31 Tips for those nearing retirement44:15 Upcoming workshop with Chip48:47 Wisdom bumper sticker50:51 How does Marc measure success54:00 Wrapping upLearn more about MEA at https://www.meawisdom.com/#MarcFreedman #EncoreCareers #ModernElder #MidlifeReinvention #FindingPurpose #LifeAfterRetirement #GenerationalCollaboration #CrossGenerational #AgingWell #WisdomAtWork #EncoreOrg #CoGenerate #ModernElderAcademy #SecondActCareers #PurposeDrivenLife


