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

    Why You Keep Repeating the Same Conflict Patterns | Diana Chapman

    Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead. In this episode of Midlife Chrysalis, Chip Conley talks with Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership. Drawing from decades of coaching founders and CEOs, Diana shares practical wisdom on how awareness can transform relationships, leadership, and personal growth. In this conversation, she explores: How the Drama Triangle fuels conflict and how to step out of itWhy playfulness is essential in long-term relationshipsThe difference between your zone of excellence and your zone of geniusWhy midlife transformation often requires quiet and surrender The episode also turns deeply personal as Chip reflects on mortality, purpose, and stepping away from constant busyness to reconnect with what matters most. Watch the full episode to explore what a true midlife chrysalis can look like. Timestamps: 03:43 Diana’s path to conscious leadership 07:37 Teach the Class tool 09:03 The Drama Triangle explained 10:43 Personas and playful awareness in relationships 12:31 Lessons from a 44-year marriage 14:32 The 15 Commitments of Conscious Leadership 16:55 Conscious leadership in today’s polarized world 17:53 The new book No Drama Teams 22:05 Trust vs threat in team dynamics 24:26 Coaching leaders through crisis 27:53 What makes a great coach 33:10 Discovering your zone of genius 36:28 Diana’s midlife chrysalis experience 39:42 Chip’s idea for a “month of dying” retreat 44:20 Lessons from a founder facing death 46:04 The value of fallow ground and quiet time 47:18 Designing a life of aliveness 48:36 Wisdom vs knowledge in the age of AI 49:26 Diana’s wisdom bumper sticker 50:21 Childhood truth and trusting your inner knowing 52:30 Reflections on truth, growth, and love 55:17 Closing reflections and invitation to the workshop Learn more about MEA at ⁠https://www.meawisdom.com/ #DianaChapman #ConsciousLeadership #15CommitmentsOfConsciousLeadership #DramaTriangle #ConsciousLeadershipGroup #ZoneOfGenius #LeadershipCoaching #ConsciousLeadershipTools #NoDramaTeams #LeadershipMindset #EmotionalIntelligence #SelfLeadership #LeadershipTransformation #ConsciousLiving #MidlifeChrysalis

    56 min

  2. 3D AGO

    From Ego to Soul: Rewriting the Second Half of Life

    The drive that made you successful may not be meant to lead you forever. In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens when achievement stops being enough. In this conversation, you’ll learn: Why ego builds the first half of life but can limit the secondHow to move from performer to elderWhat generativity really meansWhy awe and space are essential for soul growth If you’ve felt a quiet nudge that there’s something deeper beyond success, this episode will resonate. Tune in and consider who’s driving your life now. Timestamps: 01:13 Gehl’s Proud Dad Moment 04:17 Enneagram and Early Identity 06:20 Coming Out and Authenticity 09:40 The Ballroom Dance Metaphor 11:47 Richard Rohr and Falling Upward 14:14 Living Stuck in Ego 15:24 Ego, Generativity, and Aging 18:22 From Frontman to Guide 19:30 Reincarnation & Evolving Conciousness 21:32 Where People Get Stuck 25:07 Spirituality & Seeking Awe 26:06 Practices to Soften the Ego 27:26 Richard Rohr Workshop in Santa Fe Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeCrisis #MidlifeTransformation #FindingPurpose #LifeAfter50 #PersonalGrowth #SpiritualGrowth #SelfDiscovery #IdentityShift #PurposeDrivenLife #EgoVsSoul #SecondHalfOfLife #MeaningInLife #InnerGrowth #ModernElder #MidlifeAwakening

    24 min

  3. 5D AGO

    Mortality Was My Wake-Up Call | Dr. Brad Jacobs

    What if the real key to longevity isn’t a biohack but a wake-up call? In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly helps us thrive in midlife. After losing his father to cancer at 27, Brad made it his life’s work to understand how we can live longer and better. In this episode, we explore: What actually extends your life (and what’s a distraction)Why sleep and stress matter more than most supplementsHow psychedelics are reshaping emotional healingWhat modern masculinity has to do with longevityWhy midlife is a powerful reset, not a decline If you’re in your second half and ready to live with more vitality, clarity, and purpose, this conversation will challenge and inspire you. Press play! Your midlife upgrade starts here. Timestamps: 04:10 Martial arts to longevity medicine 08:58 Rethinking US healthcare 11:26 Integrative health in midlife 14:42 Sleep optimization and wearables 18:02 Longevity myths and overtraining 19:13 Food philosophy and Blue Zones 21:59 Stress overload and chronic disease 25:50 Love, partnership and second chances 29:57 Psychedelic medicine and ketamine 35:11 Ketamine vs. Psilocybin 37:45 Modern masculinity redefined 41:08 Chip on coming out & courage 48:50 Live Longer Age Better workshop 50:28 Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #Longevity #MidlifeHealth #HealthyAging #IntegrativeMedicine #LiveLonger #PsychedelicTherapy #KetamineTherapy #ModernMasculinity #MidlifeReset #SleepOptimization #BlueZones #EmotionalHealth #Biohacking #PreventChronicDisease #MidlifeTransformation

    55 min

  4. MAR 6

    Why Midlife Feels Like Exile And Why That’s a Gift | David Whyte

    In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meaning. Drawing on poetry, psychology, and Dante’s famous “dark wood,” David explains how moments of uncertainty can become powerful turning points in our lives. In this conversation, he shares: Why midlife can feel like exile from your old lifeWhat Dante’s “dark wood” teaches about transformationWhy silence and the unknown are essential for growthHow vulnerability and grief can lead to wisdom If you’ve ever felt lost, stuck, or questioning the direction of your life, this conversation offers a powerful new way to see it. 👉 Watch the full episode and discover why getting lost in midlife might be the beginning of something greater. Timestamps: 02:29 What “Midlife Chrysalis” Really Means 06:37 Dante and the Exile of Midlife 13:00 Aging, Eldership and the Inner Horizon 17:40 The Power of Silence and Contemplation 22:55 Poetry, Discipline and Inner Transformation 27:01 Why People Turn to Poetry in Midlife 33:13 Masculinity, Friendship, and Emotional Isolation 37:39 Work as a Spiritual Pilgrimage 44:22 The First Step to Deeper Conversations 50:00 Friendship with the Unknown 52:30 Vulnerability, Care, and Asking for Help 55:09 Wisdom Learned Between 50 and 70 58:27 Final Reflections on Caring and Presence Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifecrisis #midlifetransformation #midlifeawakening #midlifejourney #personalgrowth #selfdiscovery #lifeafter40 #lifeafter50 #purposeinlife #innertransformation #philosophyoflife #poetryandwisdom #dantesinferno #spiritualgrowth #meaningoflife

    1h 3m

  5. MAR 4

    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

  6. MAR 2

    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

  7. FEB 27

    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

  8. 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
See All (81)

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
    81
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

You Might Also Like