The Midlife Chrysalis

Chip Conley
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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. 1 DAY AGO

    Men vs Women in Midlife: The Struggles No One Warns You About

    Most people imagine a midlife crisis as sports cars, bad decisions, and dramatic life changes. But what if midlife is actually something much deeper and more meaningful? In this episode of Midlife Chrysalis, Chip Conley explores what really happens during midlife and why men and women often experience it differently. Chip shares insights from years of research and thousands of midlife transitions, revealing the real challenges people face in their 40s, 50s, and beyond. In this conversation, you’ll learn: Why midlife is often a feeling of being stuck, not a crisisThe hidden struggles men face, including hormonal decline, loneliness, and loss of purposeWhy many women experience invisibility and financial pressure in midlifeHow menopause, andropause, and identity shifts reshape relationships and self-confidenceWhy the real question in midlife becomes “How will you invest your wisdom?” If you’re navigating midlife, or preparing for it, this episode offers a powerful new way to understand this stage of life. Watch the episode to see how midlife can become a turning point, not a breakdown. Timestamps: 00:00 Welcome to Wisdom Wednesday 00:30 When Organizations Go Through Midlife 03:17 Change Management vs. Transition Management 05:00 Hormones and Andropause in Men 07:38 Career and Financial Disappointment 08:22 Growing Irrelevance in Midlife 09:20 Male Loneliness and Social Disconnection 10:06 Loss of Purpose After Career Changes 10:47 Low Testosterone and Men’s Health 13:55 Self-Esteem and Midlife Relationships 15:17 The Pain of Becoming Irrelevant 17:23 Menopause and Hormonal Changes for Women 19:34 The Pressure of Conventional Beauty 20:38 Invisibility in Dating and Work 22:04 Financial Challenges for Women 22:55 The Burden of Endless Caregiving 23:34 Hormone Replacement Therapy Debate 26:37 Communication in Relationships 27:19 Final Advice for Navigating Midlife Learn more about MEA at ⁠https://www.meawisdom.com/ #midlifecrisis #midlifetransition #midlifechanges #menvswomen #midlifepsychology #perimenopause #menopause #andropause #midlifeloneliness #midlifepurpose #agingandpurpose #modernelderacademy #chipconley #midlifeidentity #midlifeawakening

    26 min

  2. 3 DAYS AGO

    Why Love Requires Skills Most People Never Learn

    Why do so many relationships lose intimacy over time, even when love is still there? In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it. In this conversation, he explains: Why love requires skills most people were never taughtHow childhood patterns quietly shape adult relationshipsWhy traditional masculinity often blocks emotional intimacyHow couples can reignite connection in midlife Terry argues that relationships don’t fail because people stop caring, they fail because no one teaches us how to do intimacy well. Watch the episode to learn the relationship skills that can change everything. Timestamps: 01:30 Terry Real joins from Anguilla 03:01 What is Relational Life Therapy (RLT) 03:54 Why RLT takes sides in couples therapy 06:18 The core principles of RLT 08:14 Trauma triggers and childhood patterns in relationships 11:59 What holds men back in relationships 15:04 Redefining masculinity for intimacy 16:25 Patriarchy and the modern relationship crisis 18:23 Relational joy vs gratification culture 22:44 Reigniting intimacy as empty nesters 27:03 Why couples must confront resentment 29:46 Independence vs connection in long-term relationships 33:24 Are you really happy in your relationship 36:53 Why relationships require practice and skill 40:08 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #midliferelationships #relationshipadvice #intimacy #modernrelationships #couplestherapy #loveskills #relationshipskills #midlifechrysalis #emotionalintimacy #terryreal #relationshipgrowth #relationshipproblems #communicationinrelationships #longtermrelationships #midlifelove

    48 min

  3. 6 DAYS AGO

    Pete Holmes on Psychedelics, God & Finding Meaning in Midlife

    The moment that breaks your life can also be the moment that transforms it. In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhood, and what it really means to live a good life. In this episode, Pete reveals: How his divorce became the turning point that changed his life and careerWhy humor may be one of the most powerful tools for healingWhat psychedelics taught him about consciousness and awarenessWhy midlife can actually be the most meaningful chapter of lifeThe life-changing idea: don’t believe everything you think Warm, honest, and thought-provoking, this conversation explores how laughter and self-awareness can transform even life’s hardest moments. 👉 Watch the full episode to hear Pete Holmes’ story and discover why humor might be the secret to a better life. Timestamps: 03:46 Is Pete Christian Comedian? 06:25 Was Jesus Funny? 09:04 Humor Humility and Getting Older 10:44 Can You Train Your Sense of Humor? 13:41 Why Midlife Is Actually Better 15:36 Fatherhood and Life in His 40s 19:52 Turning 47 and the Happiness Curve 20:59 Divorce at 28 and the Turning Point 26:17 Why Comedy Exploded After 9/11 30:42 Humor as Healing for Pain 31:54 Comedy Is Saying What Everyone Thinks 35:46 Aging What Gets Worse and What Gets Better 39:50 Psychedelics and Spiritual Awakening 46:39 Bringing Spirituality Into Comedy 49:48 Pete Holmes’ Best Life Advice 54:33 Relationship Advice That Actually Works 56:19 Final Thoughts and Richard Rohr Learn more about MEA at ⁠https://www.meawisdom.com/ #PeteHolmes #MidlifeChrysalis #MidlifeWisdom #ComedyPodcast #PeteHolmesInterview #StandUpComedy #SpiritualityAndComedy #MidlifeGrowth #PersonalGrowthPodcast #PsychedelicInsights #RichardRohr #LifeLessonsPodcast #ConsciousComedy #SpiritualAwakening #SelfDiscovery

    1hr 2min

  4. 18 MAR

    Midlife Pit Stop: Refuel Before the Next Chapter

    What if the most powerful move you could make at midlife… is to pause? In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement. Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter. In this conversation, you’ll learn: Why a sabbatical isn’t a vacation. It’s renewalHow stepping away can strengthen your career and relationshipsWhat Chip discovered during his own two-year breakHow to design a meaningful month off, even if a year feels impossible Midlife isn’t about slowing down. It’s about getting intentional. If this resonates, share it with someone who might need a reset and subscribe for more Wisdom Wednesday insights. Timestamps: 00:05 Spring Travel Chat & Baja Living 05:34 The Rise of the Midlife Gap Year 11:20 The Midlife Atrium Concept 13:15 Why Employers Should Support Sabbaticals 17:14 Starting Small with a Gap Weekend 18:07 Chip’s Two-Year Sabbatical Experience 23:13 Ego, Curiosity, and Deepened Friendships 24:31 How to Design a One-Month Sabbatical 26:58 Saving for a Midlife Pit Stop 29:19 Escaping One-Dimensional Living Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeReset #MidlifeSabbatical #MidlifeGapYear #SecondAct #LifeAfter50 #CareerBreak #SabbaticalLife #WorkLifeBalance #RetirementRedefined #PersonalGrowthJourney #EmptyNestLife #ReinventYourLife #MidlifeTransformation #PurposeAfter50 #ChipConley

    26 min

  5. 16 MAR

    Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans

    Most of us try to solve midlife. What if that’s exactly the wrong approach? In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “figuring it all out.” Instead of chasing the right answer, Bill and Dave invite us to prototype our way forward gently, curiously, and without fear of getting it wrong. Key insights from the conversation: Midlife isn’t a crisis. It’s a chrysalis, a space for becomingThere is no single “right” life, only many good lives you can designStop solving your life and start prototyping small experimentsCuriosity matters more than certaintyMeaning isn’t found in big answers, but in everyday moments of flow This is a hopeful, grounding conversation for anyone who feels stuck, restless, or quietly ready for what’s next. 👉 Click to watch and discover how to design the next chapter of your life without pressure, panic, or pretending. Timestamps: 03:48 What Designing Your Life is 06:55 What is design thinking 09:22 Designing yourself as a wicked problem 10:20 Gravity problems and anchor problems 12:32 Opening the aperture of choice 14:03 Applying design thinking to midlife 16:49 Creativity and reinvention after success 18:03 Are midlifers more stuck than younger people 19:14 Permission to change in midlife 21:50 Prototyping your next chapter 24:08 Self-criticism fear and resistance 25:00 Learning to be incompetent again 27:49 Personal midlife transitions 31:14 Dark night of the soul 36:53 Introducing the meaning book 38:11 Designing meaning in everyday life 40:21 Redesigning midlife as a culture 44:01 Rethinking work and education 48:25 Reframing midlife identity 52:07 Wisdom bumper stickers Learn more about MEA at ⁠https://www.meawisdom.com/ #MidlifeChrysalis #DesignYourLife #MidlifeTransition #FindingPurpose #SecondHalfOfLife #LifeDesign #MidlifeMeaning #PersonalGrowth #MidlifeReinvention #DesignThinking #CareerTransition #CuriosityMindset #ModernElder #MidlifeWisdom #LifeAfter40

    57 min

  6. 13 MAR

    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

  7. 11 MAR

    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

  8. 9 MAR

    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
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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
    86
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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