The Midlife Chrysalis

Chip Conley
  • 4.9 (75)
  • 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 Midlife Feels Stuck (And How to Break Free)

    Don't wait until it's too late to tell someone what they mean to you. In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it? In this episode, you'll learn: Why we struggle to express appreciation when it matters most.The difference between a living funeral and a social eulogy.How anticipating loss can help you live with fewer regrets.Why meaningful human connection is more important than ever in the age of AI.A simple challenge you can put into practice today. 🎧 Watch now, and if this conversation resonates with you, like, subscribe, and share it with someone who deserves to hear how much they matter. Timestamps: (00:00) Introduction (01:18) What Is a Living Funeral? (03:02) The Social Eulogy Explained (07:19) Seeing Your Impact on Others (08:01) Why Age 50 Is the Perfect Time (09:20) Why We Wait to Express Appreciation (10:42) The Power of Anticipating Loss (11:36) The Cost of Leaving Things Unsaid (12:30) Lessons From People at the End of Life (14:11) Who Should Be Part of a Social Eulogy? (16:32) Becoming More Human in the Age of AI (17:33) This Week's Challenge (18:54) Why This Gift Costs Nothing (19:18) Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #SocialEulogy #LivingFuneral #MidlifeChrysalis #WisdomWednesday #ModernElder #MeaningfulRelationships #HearYourEulogy #LeaveNothingUnsaid #HumanConnection #LifeLessons #Legacy #MidlifeWisdom #EmotionalWellbeing #RelationshipAdvice

  2. 3d ago

    How Psilocybin Can Change Your Life After 40 | Neil Markey

    Could one guided psychedelic experience transform the way you think, feel, and live? In this episode of The Midlife Chrysalis, Chip Conley speaks with Neil Markey, CEO of Beckley Retreats, former Army Ranger captain, McKinsey consultant, and Harvard public health student, about the growing role of psilocybin in personal transformation and mental well-being. Together, they explore: Why midlife may be the ideal time for a psychedelic experience.What really happens during a professionally guided psilocybin retreat.Why preparation and integration are just as important as the experience itself.The benefits, risks, and biggest misconceptions about psychedelic therapy.How meditation, nature, and new habits can create lasting change. Whether you're curious about psychedelics or looking for new ways to navigate midlife, this conversation offers a thoughtful, evidence-informed perspective on one of today's most talked-about topics. If you enjoyed this episode, like, subscribe, and share it with someone who would find it valuable. Timestamps: (00:00) Introduction (01:54) Neil Markey's Background (06:53) First Psilocybin Experience (09:45) The Story Behind Beckley Retreats (15:53) Amanda Fielding's Legacy (18:20) Joining Beckley Retreats (21:31) What Happens at a Beckley Retreat (26:45) Inside a Psilocybin Session (29:26) What a Psychedelic Experience Feels Like (33:33) Why Midlife Is the Right Time (40:20) The Importance of Integration (43:11) The Future of Psychedelics in the US (47:36) Life Lessons and Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #Psilocybin #Psychedelics #PsychedelicTherapy #MentalHealth #Midlife #MidlifeTransformation #PersonalGrowth #Healing #Meditation #SelfDiscovery #Wellness #Neuroplasticity #MentalWellbeing #BeckleyRetreats #TheMidlifeChrysalis

  3. 6d ago

    Your Brain Is Lying to You About Happiness | Dr. Laurie Santos

    We've been chasing happiness the wrong way. Dr. Laurie Santos explains what actually works. Join Chip Conley and Dr. Laurie Santos, Yale's renowned happiness professor and creator of the university's most popular course, for a thought-provoking conversation on the science of happiness, the opportunities of midlife, and the habits that lead to a more fulfilling life. In this episode, you'll discover: Why your brain often pushes you toward the wrong definition of successThe habits that matter more than money, achievement, or statusHow your mindset can shape your happiness, health, and even longevityWhy midlife is the perfect time to rethink your priorities and invest in what truly mattersThe simple piece of advice Laurie wishes she'd learned much earlier in life If you've ever wondered whether you're spending your time on the things that really matter, this conversation will change the way you think about happiness, purpose, and the second half of life. If you enjoyed this episode, like, subscribe, and share it with someone who could use a fresh perspective on living well. Timestamps: (02:10) Meet Dr. Laurie Santos (03:13) Growing Up and Finding Purpose (05:19) Studying Monkeys at Harvard (07:23) What Monkeys Teach Us About Human Thinking (09:08) The Most Popular Class at Yale (12:24) The Science of Happiness (16:40) How Mindset Shapes Longevity (18:47) Turning 50 and Rethinking Midlife (21:51) The Power of Midlife Rituals (25:00) Why Everyone Needs a Sabbatical (30:44) Giving Back and Building Strong Relationships (32:50) The Future of Higher Education (37:04) It Doesn't Matter as Much as You Think (38:24) Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #LaurieSantos #ChipConley #HappinessScience #PsychologyOfHappiness #PositivePsychology #Midlife #MidlifeChrysalis #Mindset #HealthyAging #Longevity #SocialConnection #PurposeInLife #Yale #HappinessResearch #LiveWell

  4. Aug 5

    Why High Achievers Still Feel Like Imposters

    Do you ever feel like you're not good enough, even when you're succeeding? You're not alone. In this Wisdom Wednesday, Chip Conley explores why imposter syndrome follows so many high achievers and, more importantly, how to break free from it. In this conversation, you'll discover: Why imposter syndrome doesn't disappear with successHow to replace fear with curiosity and become an "explorer" instead of an imposterWhy vulnerability often earns more respect than pretending to be perfectA simple mindset shift that makes taking risks feel much less overwhelmingHow embracing beginner status can unlock growth at any stage of life If you've ever questioned your abilities, avoided new opportunities, or felt held back by self-doubt, this episode offers practical insights that can help you move forward with greater confidence. Watch now, and if you enjoy the conversation, don't forget to like, subscribe, and share it with someone who needs this reminder. Timestamps: (00:00) Introduction (00:36) What Is Imposter Syndrome? (03:28) Growth Mindset vs Fixed Mindset (05:21) Use Humor to Quiet Your Inner Critic (06:27) Curiosity Over Fear (08:02) Why Vulnerability Builds Trust (13:05) From Imposter to Explorer (14:34) Career Transitions in Midlife (17:36) Above vs Below the Waterline Decisions (20:39) How AI Helps You Learn (22:39) The Human Skills AI Can't Replace (24:21) A Simple Exercise for Imposter Syndrome Learn more about MEA at ⁠https://www.meawisdom.com/ #ImposterSyndrome #SelfDoubt #GrowthMindset #HighAchievers #CareerTransition #Midlife #PersonalGrowth #Mindset #Confidence #Vulnerability #FearOfFailure #ChipConley #ModernElderAcademy #MidlifeChrysalis #EmotionalIntelligence

  5. Aug 3

    The Biggest Lies We've Been Told About Aging | Ashton Applewhite

    In this eye opening conversation, bestselling author and aging activist Ashton Applewhite challenges everything we think we know about growing older. She reveals why many of our fears about aging come from culture, not reality, and explains how getting older can bring more freedom, confidence, and purpose. In this episode, you'll learn: Why ageism is one of the last socially accepted forms of prejudiceWhy the conflict between younger and older generations is largely a mythHow society pressures us to follow a rigid life timelineWhy confidence and emotional resilience often increase with ageWhat the longevity movement gets wrong about living a meaningful life Watch now to discover a healthier, more empowering way to think about aging, purpose, and the years ahead. Timestamps: (02:02) Is America Becoming Ageist? (08:44) Why Generations Need Each Other (11:32) Why We Fear Getting Older (14:39) The Biggest Myth About Aging (16:47) Midlife and Chrononormativity (21:54) Ashton Applewhite's Journey (27:43) What Gets Better With Age (34:31) The Problem With Longevity Culture (40:12) Wisdom, Curiosity, and Lifelong Growth Learn more about MEA at ⁠https://www.meawisdom.com/ #Aging #Ageism #HealthyAging #GrowingOlder #PositiveAging #Longevity #OlderAdults #Midlife #LifePurpose #PersonalGrowth #Psychology #Intergenerational #AgeDiversity #WellBeing #AshtonApplewhite

  6. Jul 31

    Why Your 70s Can Be Your Most Meaningful Years | Dr. Philip Pizzo

    What if your most meaningful chapter begins after 70? Most people think aging is about slowing down. Dr. Philip Pizzo believes it's about discovering new purpose. In this inspiring conversation, Chip Conley sits down with Dr. Philip Pizzo, former Dean of Stanford Medicine, founder of the Stanford Distinguished Careers Institute (DCI), physician, educator, and now a spiritual care provider, to explore how we can navigate life's biggest transitions with meaning. In this episode, you'll discover: Why purpose, community, and wellness are the foundation of a fulfilling second half of life.The unexpected journey that led Dr. Pizzo to reinvent himself and begin a new calling in his 70s.What he learned from helping hundreds of professionals successfully navigate midlife transitions.Why community becomes one of the greatest predictors of healthy aging and longevity.How to approach aging with curiosity, purpose, and a growth mindset. If you're wondering what comes after success, retirement, or your next big life transition, this conversation will change the way you think about aging. Watch now and discover why it's never too late to reinvent yourself. Timestamps: (02:20) Phil Pizzo’s Childhood & Education (04:22) Life Transitions and Finding New Purpose (10:15) Converting to Judaism in His 70s (13:27) Spiritual Care After a Career in Medicine (15:28) Life in a Retirement Community (21:44) Modern Day Aging & Longevity (25:32) Staying Active in Your 80s (26:39) The Story Behind Stanford DCI (29:15) What DCI Taught About Midlife (32:23) The Real Purpose of Midlife (37:44) Rethinking Aging and Medicine (41:21) Phil Pizzo’s Advice for Living Well Learn more about MEA at ⁠https://www.meawisdom.com/ #PhilipPizzo #MidlifeChrysalis #PurposeAfterRetirement #SuccessfulAging #Longevity #StanfordDCI #LifeReinvention #HealthyAging #RetirementPurpose #SecondHalfOfLife #LifeTransitions #SpiritualGrowth #MeaningfulLife #CommunityAndConnection #AgingWell

  7. Jul 29

    Don't Save It for the Funeral: The Power of a Social Eulogy

    Don't wait until it's too late to tell someone what they mean to you. In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it? In this episode, you'll learn: Why we struggle to express appreciation when it matters most.The difference between a living funeral and a social eulogy.How anticipating loss can help you live with fewer regrets.Why meaningful human connection is more important than ever in the age of AI.A simple challenge you can put into practice today. 🎧 Watch now, and if this conversation resonates with you, like, subscribe, and share it with someone who deserves to hear how much they matter. Timestamps: (00:00) Introduction (01:18) What Is a Living Funeral? (03:02) The Social Eulogy Explained (07:19) Seeing Your Impact on Others (08:01) Why Age 50 Is the Perfect Time (09:20) Why We Wait to Express Appreciation (10:42) The Power of Anticipating Loss (11:36) The Cost of Leaving Things Unsaid (12:30) Lessons From People at the End of Life (14:11) Who Should Be Part of a Social Eulogy? (16:32) Becoming More Human in the Age of AI (17:33) This Week's Challenge (18:54) Why This Gift Costs Nothing (19:18) Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #SocialEulogy #LivingFuneral #MidlifeChrysalis #WisdomWednesday #ModernElder #MeaningfulRelationships #HearYourEulogy #LeaveNothingUnsaid #HumanConnection #LifeLessons #Legacy #MidlifeWisdom #EmotionalWellbeing #RelationshipAdvice

  8. Jul 27

    The Hero’s Journey: Crossing the Threshold from Stagnation to Generativity | Pat Whitty

    At an age when many people are slowing down, Pat Whitty walked 200 miles on Spain's Camino de Santiago — alone. But what started as a physical challenge became a profound journey of self-discovery, purpose, and spiritual renewal. In this inspiring conversation, Chip Conley sits down with Pat to explore what happened when he stepped away from the noise of everyday life and spent 16 days walking with nothing but his thoughts. In this episode, you'll discover: Why it's never too late to pursue a dream you've been putting off for years.How walking the Camino helped Pat let go of the need to prove himself and embrace who he truly is.The surprising lessons about purpose, aging, and finding meaning after major life setbacks.Why rituals, curiosity, and human connection become even more important as we grow older.Practical advice for anyone considering walking the Camino, regardless of age. hether you're seeking purpose or a fresh perspective on life, this episode is for you. Watch now, and don't forget to like, subscribe, and share! Timestamps: (05:07) Deciding to Walk the Camino at 84 (06:48) From Outer Journey to Inner Journey (12:52) Letting Go of People-Pleasing (17:56) The People You Meet on the Camino (22:06) A Stranger's Unexpected Kindness (24:41) A Spiritual Journey, Not Just a Hike (29:15) Why Rituals Give Life Meaning (30:18) Camino Tips for Beginners (35:17) Finding Purpose Later in Life (40:54) It's Never Too Late for an Adventure (43:00) Wisdom for a Meaningful Life Learn more about MEA at ⁠https://www.meawisdom.com/ #CaminoDeSantiago #HealthyAging #Purpose #PersonalGrowth #Adventure #ActiveAging #LifeLessons #AgingWell #Midlife #Retirement #SelfDiscovery #Inspiration #Walking #SpiritualJourney #ChipConley

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Trailer

4.9
out of 5
75 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
    146
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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