The Midlife Chrysalis

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

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

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

Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive.From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the seven playful experiments from her new book In Defense of Dabbling that prove it’s never too late to try something new.Packed with heart, humor, and practical wisdom, this episode will leave you smiling and inspired to chase your own adventures.Timestamps:00:00 Intro00:45 Introduction to Karen Walrond01:58 Growing up & career journey06:50 Midlife shift toward writing and creative work11:38 Cultural perspectives on aging in Trinidad vs. the U.S.16:55 Defining the “Radiant Rebellion”19:14 Resisting societal scripts23:06 Aging in non-white cultures31:43 Collaboration with Brené Brown36:12 Introducing In Defense of Dabbling40:03 The 7 attributes of dabbling44:08 Why trying new things matters as we age50:42 Karen’s experience teaching at MEA workshops53:11 Karen’s wisdom bumper sticker57:10 Chips’s closing reflections on joy, culture, and lifelong learningLearn more about MEA at ⁠https://www.meawisdom.com/#AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost?In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing.If you’ve ever felt stuck, out of alignment, or afraid to be fully yourself—this episode will change how you see everything.Timestamps:00:00 Intro00:56 Meet Martha Beck03:02 Growing Up Mormon, Academic Journey, and Her Son’s Diagnosis10:53 Leaving Mormon Church & Reframing Midlife14:47 Losing Religion, Finding Soul, and Polyamory19:20 Returning to True Nature Through Rebellion21:23 Lessons from Her Son with Down Syndrome27:10 Psycho-Neuro-Immunology & Integrity30:58 Shaman Sickness & Becoming a Healer33:24 A Simple Path to Inner Stillness40:01 The Radical Power of Not Lying41:43 How to Listen to Your Body’s Response52:27 Martha’s Bumper Sticker WisdomLearn more about MEA at ⁠https://www.meawisdom.com/#MarthaBeck #ChipConley #TheWayOfIntegrity #MidlifeTransformation #SpiritualAwakening #LeavingMormonism #DownSyndromeParenting #PolyamoryJourney #LifePurpose #InnerHealing #TrustYourself #ModernElder #SelfDiscovery #PsychicExperiences #AnxietyAwareness

Sara Blakely, the founder of Spanx, shares her entrepreneurial journey from selling fax machines to creating a billion-dollar brand. She discusses the emotional challenges of selling Spanx and her identity shift in midlife. Blakely emphasizes the importance of intuition, vulnerability, and redefining success beyond business. She also dives into her new venture, Sneaks, blending style and comfort in footwear. Her insights on growth, resilience, and embracing one's feminine energy make for an inspiring conversation about navigating personal transformations.

In this enlightening conversation, Pico Iyer, a celebrated writer and long-time friend of the Dalai Lama, shares invaluable insights from their 50-year friendship. He explores the concept of midlife as a breakthrough rather than a breakdown, emphasizing the importance of letting go to find true freedom. Pico discusses his transformative move from New York to Kyoto, the significance of stillness, and practical mindfulness tips. He reflects on the wisdom gleaned from life's contradictions and the urgency of living fully as we age.

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond.Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son RelationshipLearn more about MEA at ⁠https://www.meawisdom.com/#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut

What happens when one of the most thoughtful voices in public life hits a wall?In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too late to begin again, so don’t miss this one.Subscribe for more powerful conversations that spark reflection, reinvention, and real change in midlife.Timestamps:00:00 Welcome and Setup00:46 Introducing Lee and the Unique Cast of Guests01:52 What Makes a Great Interviewer?06:12 Interviewing John O’Donohue09:57 Thresholds and Transitions12:58 Krista’s Childhood and Upbringing in Oklahoma17:40 The Bible as Her First Text of Imagination20:00 Interviewing Richard Rohr and Men’s Spiritual Lives23:36 Krista’s Midlife Reflections27:06 Midlife Chrysalis and Personal Transformation30:53 Building a Life Around Love and Friendship35:36 What She’d Regret Not Doing38:09 What Brings Joy Now42:03 Defining Wisdom and Growing Wiser46:26 Staying Grounded Through Rituals and Attention51:43 Rethinking Retirement54:29 The Aging Brain and Synthesizing Wisdom57:46 Wisdom Bumper StickerLearn more about MEA at ⁠https://www.meawisdom.com/#MidlifeWisdom #OnBeing #KristaTippett #MidlifeTransformation #SpiritualGrowth #LifeAfter40 #InnerLife #FindingPurpose #EmotionalResilience #WomenOver40 #BecomingWise #SoulfulLiving #PersonalGrowthJourney #AgingWithGrace #DeepConversations

What if your so-called “midlife crisis” was actually a doorway to reinvention? In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your most creative and meaningful chapter yet.Timestamps:00:00 Intro00:40 Chips Connection to Burning Man04:43 What Burning Man Really Is07:01 How Burning Man Became a Global Movement08:47 The Core Principles That Guide Everything11:13 Radical Self-Expression and Creating Without Expectation13:38 Why Burning Man Attracts People in Midlife Transition16:43 Loss, Legacy, and What We Leave Behind21:46 Lessons from Larry Harvey as a Modern Elder25:05 What She Learned as a Burning Man’s CEO33:00 What Is Fly Ranch and Why It Matters36:28 Fly Ranch Like Burning Man’s Feminine Side39:24 Three Tips for Burning Man First-Timers42:14 Burning the Man and Temple Rituals47:22 The Healing Power of Ritual50:08 Why MEA Resonates with Burners53:40 Wisdom Bumper StickerLearn more about MEA at ⁠https://www.meawisdom.com/#BurningMan #MidlifeCrisis #MidlifeTransformation #MarianGoodell #BurningMan2025 #PersonalGrowth #ReinventionAfter40 #MidlifeAwakening #LifeAfter50 #SpiritualJourney #BurningManExperience #RadicalSelfExpression #MidlifeChrysalis #ChipConley #PurposeInMidlife