The Midlife Chrysalis

Chip Conley
  • 5.0 (51)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

  1. 1D AGO

    Letting Go in Midlife: What Has Run Its Course?

    Midlife isn’t about adding more. It’s about letting go. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore The Great Midlife Edit, the courage to release what has quietly run its course. Drawing from his near-death experience and the sale of his company, Chip shares what it really means to “empty your cup” and create space for what’s next. In this conversation, you’ll learn: Why midlife shifts us from accumulation to editingHow to recognize what’s ready to “graduate” from your lifeThe three stages of transition — endings, the messy middle, and new beginningsA powerful question to help you begin your own edit If something in your life feels heavy, outdated, or complete, this episode is your gentle invitation to let go and begin again. Listen in, reflect, and share it with someone ready for their next chapter. Timestamps: 00:00 Welcome to Wisdom Wednesday 00:18 Heated Rivalry and Mark Carney 03:29 The Great Midlife Edit 07:10 Empty Your Cup Japanese Story 10:15 Transitional Intelligence and Endings 11:46 Surrender and the Serenity Prayer 15:15 Chip’s Major Life Edits 18:45 Gut Check Practice 20:22 Editing Family Relationships 22:29 Question to Begin Your Own Edit 24:10 Ritualizing Letting Go Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #MidlifeTransition #MidlifeReset #LettingGo #LifeTransitions #SecondAct #PersonalGrowth #Reinvention #EmptyYourCup #TransitionalIntelligence #PurposeInMidlife #LifeAfter50 #EmotionalWellbeing #SabbaticalLife #ChipConley

    22 min

  2. 3D AGO

    Greg Louganis: Olympic Gold, Public Masks, Private Truth

    What happens when the world sees a champion… but you’re still figuring out who you are? In this episode of The Midlife Chrysalis, Olympic legend Greg Louganis opens up about the life behind the gold medals and the deeper journey beyond fame. From childhood wounds and public adoration to living with HIV and facing mortality at 28, Greg shares how his identity has evolved over decades. You’ll hear: • How early trauma shaped his drive to perform • Why love, not medals, fueled his career • What midlife taught him about letting go of personas • How meditation, shadow work, and silence helped him heal This is a conversation about reinvention, mortality, and becoming whole, not despite your past, but because of it. If you’re navigating midlife, identity shifts, or personal healing, this episode will speak to you. 👉Press play and enter the chrysalis. Timestamps: 02:50 Welcome to Midlife Chrysalis 03:13 Moving to Panama and new chapter 04:50 First trauma and feeling abandoned 11:20 Performing and early competition 16:01 Olympic journey and first medals 17:14 Fame and public attention 20:40 Coach Ron O’Brien and motivation 24:55 Identity, HIV, and sponsorship struggles 29:28 Living with public persona 33:29 Evolving identity and being content 36:37 Meditation yoga and inner work 42:11 Looking inward for answers 44:39 Life wisdom and 45-year relationship 49:22 Mortality, HIV, and acceptance of death Learn more about MEA at ⁠https://www.meawisdom.com/ #GregLouganis #MidlifeChrysalis #OlympicLegend #HIVAwareness #MidlifeTransformation #PersonalGrowthJourney #IdentityShift #HealingJourney #ShadowWork #MeditationPractice #FacingMortality #Reinvention #LGBTQVoices #ResilienceStory #FromFameToFreedom

    51 min

  3. 6D AGO

    Midlife and the Moral Pressure of Limited Time | Kieran Setiya

    Midlife can feel unsettling even when life looks successful on paper. This episode explores why that discomfort appears and how it can become a source of clarity rather than crisis.  Our guest is Kieran Setiya, MIT philosophy professor and author of Midlife: A Philosophical Guide. Drawing from philosophy and lived experience, he offers a calm, deeply human way of understanding regret, time, ambition, and meaning in the middle years of life.  In this conversation, you will learn: Why midlife is shaped by the past we cannot undo and a future that feels shorterHow goal chasing can quietly drain meaning from everyday lifeThe difference between living for outcomes and living through meaningful processesWhy regret and existential FOMO are signs of a rich value system, not personal failureHow attention, attachment, and acceptance create a more grounded way to live This episode is thoughtful, reassuring, and deeply practical for anyone questioning direction, purpose, or satisfaction in midlife. Listen now and discover a wiser, steadier way to meet the second half of life.  Timestamps: 02:59 Early interest in philosophy 05:28 Philosophy and physics connection 07:03 Why write about midlife 10:15 What defines midlife 12:46 Pressures, regret, and time poverty 15:27 Telic and atelic activities 20:03 Intrinsic and extrinsic motivation 21:23 Flow and engagement 22:37 Finding atelic activities 25:24 Chronos and Kairos 30:00 Anticipated regret as wisdom 34:48 Choosing a personal philosophy 37:38 Philosophers Kieran admires 40:47 When midlife ends 43:42 Philosophy and young people 48:19 Philosopher as president 51:03 Making philosophy practical 53:26 A life philosophy bumper sticker 57:37 Attachment and responsibility  Learn more about MEA at ⁠https://www.meawisdom.com/  #kieransetiya #midlifephilosophy #telicvsatelic #midlifereckoning #existentialregret #meaningoverachievement #philosophyofmidlife #timeandmeaning #midlifereflection #existentialfomo #processovergoals #lifewithoutburnout #modernelderacademy #attentionandmeaning #livingwellmidlife

    1h 2m

  4. FEB 25

    What a Cancer Diagnosis Teaches You About How to Live

    What happens when time stops feeling endless and starts feeling real? In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife. Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear. Together they explore: Why memento mori can bring clarity, not darknessHow midlife urgency is about intention, not panicWhat legacy really means beyond achievement This is a warm, life-affirming conversation about choosing what matters most when you realize tomorrow isn’t guaranteed. 👉 Watch now, and join the conversation by leaving a comment or review. Timestamps: 00:00 Opening and setup 00:42 Episode introduction 01:00 Workshops and unexpected contrasts 03:12 Ricky Williams and walking away from football 04:28 Cancer scans and living with uncertainty 05:20 Death as a daily presence 06:00 Prostate cancer diagnosis and treatment journey 10:43 Hormone therapy and energy loss 13:46 Feeling mortality in the body 14:16 Memento mori and midlife urgency 16:30 Legacy and ripple of impact 18:24 Near death experience story 22:47 Succession planning and leadership wisdom 23:18 Talking about death without fear 26:10 Purpose usefulness and meaning 28:20 Wisdom bumper sticker on mortality 30:04 Gratitude and closing reflections Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeWisdom #CancerJourney #LivingWithUrgency #MementoMori #MidlifePurpose #FacingMortality #LifeAfterCancer #ModernElder #MeaningfulLife #LegacyAndPurpose #MidlifeReflection #WisdomWednesday #PersonalGrowth #LifePerspective #ChipConley

    28 min

  5. FEB 22

    From Ambition to “I’m Enough” | Brian Chesky

    In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved from control to connection• The wake-up call that followed Airbnb’s $100B milestone• Why midlife is a chance to redefine what truly matters This is a conversation about growth, vulnerability, and choosing relationships over relentless achievement.If you’re navigating success, questioning your next chapter, or redefining what fulfillment means, this one’s for you.Listen in and reflect on what “enough” means in your life. Timestamps:00:00 Reunion and reflecting on 13 years since Airbnb began01:02 How Brian recruited Chip and the early Airbnb vision02:27 Chutzpah and learning from mentors04:00 Discovering hospitality as Airbnb’s true business06:43 Early partnership dynamics and mutual mentorship11:21 Advice to his 26 year old founder self12:20 Imposter syndrome and leadership growth15:42 From creative outsider to Fortune 500 CEO17:26 Childhood, not belonging and ambition22:48 Loneliness after success and the IPO realization27:54 Investing in friendships and rebuilding connection29:00 Founder mode and evolving leadership style37:24 Redefining success in midlife38:17 Hoffman process and realizing he is enough41:35 Fear of intimacy and unfinished business50:03 The Airbnb Open and scaling with soul54:20 Wisdom bumper stickers and life lessons56:04 In you lies unknown potential1:00:48 I am enough and always was Learn more about MEA at ⁠https://www.meawisdom.com/

    1h 8m

  6. FEB 20

    Your Brain on Art: Why Midlife Needs Creativity More Than Ever | Susan Magsamen & Ivy Ross

    Midlife isn’t a crisis. It’s an invitation to come alive again. In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife. Drawing from their book Your Brain on Art, they share how art, play, and sensory experiences quietly support brain health, emotional balance, and a deeper sense of meaning in a world obsessed with productivity and speed. You’ll hear why: Creativity is hard-wired into our biology, not reserved for “artists”Midlife is a powerful moment to rediscover curiosity, play, and makingSmall creative acts can reduce stress and help us feel more aliveArt may be one of the healthiest counterweights to burnout and AI The second half of life isn’t about doing more, it’s about sensing more, feeling more, and reconnecting with what truly matters. 👉 Watch now and let midlife become a chrysalis, not a cage. Timestamps: 13:35 Guest backgrounds and journeys 18:36 What Your Brain on Art is really about 21:25 Neuroaesthetics and brain science 23:54 Why creativity is essential for health 24:24 How to rebuild creativity in midlife 29:14 Art, neuroplasticity, and medicine 34:32 Creativity inside Google 39:18 Digital literacy, nature, and balance 41:35 Personal midlife transformation stories 45:30 Resilience through illness and change 49:08 Life wisdom and defining moments 55:51 Final reflections and closing Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #YourBrainOnArt #CreativityAndAging #MidlifeWellbeing #Neuroaesthetics #BrainHealth #CreativityForAdults #MidlifeGrowth #ArtAndScience #HealthyAging #MentalHealthMidlife #PurposeInMidlife #CreativeLiving #SecondHalfOfLife #MidlifeInspiration

    51 min

  7. FEB 18

    Why Midlife Friendships Stop Working & How to Fix Them

    Ever notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit. In this Wisdom Wednesday episode, Chip Conley, founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it matters more than ever, and how it can grow again. What you’ll take away: Friendship is a practice, not a personality traitMost of us outgrow conversations, not peopleDepth and vulnerability create real connectionReaching out — even after years — can reopen meaningful bondsIf you’ve ever wondered how to build friendships that actually nourish you as you age, this conversation is for you. Listen now and discover how midlife friendships can become richer, not smaller.  Timestamps: 00:13 Friends in midlife and outgrowing friendships 00:45 Friendship as a practice 02:10 Reconnecting with old friends 04:20 Outgrowing conversations not people 06:00 Depth vulnerability and the three vaults 09:40 Why friendship requires depth 10:48 Men opening up emotionally 13:05 Leading with vulnerability 13:58 Creating deeper conversations naturally 15:48 Different levels of friendship 16:39 Couples growth and shared language 17:37 Transactional vs real friends 18:02 How to rebuild friendships in midlife 20:13 Closing thoughts and wrap up  Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeFriendships, #MidlifeConnection, #FriendshipAfter40, #SecondHalfOfLife, #MeaningfulRelationships, #EmotionalIntelligence, #PersonalGrowth, #SocialConnection, #AuthenticLiving, #MidlifeWisdom, #LifeTransitions, #ProAging, #ModernAging, #HumanConnection, #WisdomWednesday

    20 min

  8. FEB 16

    Why Midlife Men Struggle with Identity & Purpose Today | Greg Scheinman

    Ever wonder what happens when “success” still feels empty? At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife. In this episode, we dive into what modern masculinity really means, why so many men struggle with identity and purpose, and how to turn a midlife crisis into a life by design. Tune in to learn how Greg turned breakdown into breakthrough and how you can too.  Timestamps: 00:00 Introduction 00:24 Early Life & Family Loss 02:38 Working for Harvey Weinstein 05:03 From Film to Entrepreneurship 08:15 Lessons on Curiosity & Reinvention1 0:53 Identity Crisis at 40 13:29 Entering the Insurance Industry 15:16 Building a PBS Show 16:57 Struggling with Identity 22:20 Tipping Point at 47 24:33 Creating Midlife Male 26:30 Marriage Problems & Masculinity 30:34 Why He Built Midlife Male 38:48 The Modern Midlife Male Dilemma 41:37 Conviction, Curiosity & Courage to Speak 45:00 The Six F’s of Life & Finding Success 49:06 Raising Sons Today 54:56 Wisdom Bumper Sticker 57:07 Learning to Be Both Hard & Soft  Learn more about MEA at ⁠https://www.meawisdom.com/ #GregScheinman #MidlifeMale #MidlifeChrysalisPodcast #ChipConley #ModernMidlifeMan #MenInMidlife #MidlifeReinvention #MidlifeIdentity #MensMentalHealthAwareness #RedefiningMasculinity #LifeByDesign #EntrepreneurInMidlife #MidlifeWisdom #PurposeBeyondSuccess #FromCrisisToGrowth

    1h 3m
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Trailer

5
out of 5
51 Ratings

About

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife. Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

Information

  • Creator
    Chip Conley
  • Years Active
    2025 - 2026
  • Episodes
    77
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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