The Midlife Chrysalis

Chip Conley
  • 4.9 (76)
  • 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. 3h ago

    From Doing to Being: The Power of Presence | Teddi Dean

    Sometimes the most powerful thing we can do is stop doing and simply be present. In this episode, Chip Conley talks with Teddi Dean, former Bones Brigade skateboarder turned filmmaker, mindfulness teacher, and Head of Mind & Body at MEA. Teddy shares his journey through sobriety, yoga, meditation, and decades of exploring what it means to live with greater awareness. You’ll discover: Why stillness can be transformative and help us reconnect with ourselves.How 10 to 20 minutes of daily mindfulness can change how we respond to life.Why mindfulness goes beyond meditation, from walking and surfing to ordinary daily activities.How listening to your body and breath can lead to wiser choices.Why paying attention makes ordinary life richer and helps us see familiar things with fresh eyes. Teddi’s hard earned wisdom is beautifully simple: Just be. Watch the full episode for a practical and inspiring conversation about becoming more present for your own life.  Timestamps: (00:00) Meet Teddi Dean (01:05) Growing Up in Skate Culture (03:03) Joining the Bones Brigade (05:20) Walking Away From Skateboarding (08:57) Drinking and Life After Skateboarding (10:04) Getting Sober at 35 (11:00) Finding Yoga and Mindfulness (14:23) Starting a New Life in Baja (17:10) Joining the Modern Elder Academy (19:04) Why Midlife Needs a Wisdom School (21:35) The Power of Silent Retreats (26:49) Learning to Sit With Yourself (28:39) Building a Daily Mindfulness Practice (30:22) Creating Space Between Stimulus and Response (32:01) Turning Everyday Activities Into Mindfulness (35:05) What Is Embodied Prayer? (36:30) Listening to the Wisdom of the Body (39:06) Becoming Amazed by the Mundane (41:18) Wisdom Bumper Sticker (43:00) Sunday Sangha  Learn more about MEA at ⁠https://www.meawisdom.com/ #TeddiDean #ChipConley #ModernElderAcademy #JustBe #PowerOfPresence #MindfulnessInMidlife #SilentRetreat #DailyMindfulness #FromDoingToBeing #MindBodyAwareness #EmbodiedPrayer #MindfulnessAndSobriety #BonesBrigade #FindingStillness #MidlifeWisdom

  2. 2d ago

    Curiosity Is the Secret to a Richer Life

    Happiness and purpose may not be enough for a truly rich life. In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness and why curiosity, new experiences, challenge, and spontaneity become especially valuable as we age. You’ll discover: Why psychological richness matters as we get older and how curiosity keeps us engaged with life.The question that can reshape your next decade: What will you regret not learning, doing, or investing in 10 years from now?Why becoming a beginner again matters, from learning a new skill to pursuing a passion you’ve neglected.Why spontaneity and stepping beyond routine enrich our lives and open us to experiences we might otherwise miss. Watch the full episode and choose one thing you’re ready to finally do.  Timestamps: (00:02) Welcome to Wisdom Wednesday (02:23) What Is a Psychologically Rich Life? (05:58) Creating More Psychological Richness (10:33) Reinventing Yourself in Midlife (12:04) What Will You Regret in 10 Years? (14:33) Is the Door Really Closed? (16:04) Why We Regret What We Don’t Do (17:48) Ways to Enrich Your Life (20:24) Pilgrimages and New Experiences (21:40) Curiosity and Leaving Your Comfort Zone (22:08) The Power of Spontaneity (24:01) This Week’s Challenge24:50 Make Your Commitment Public  Learn more about MEA at ⁠https://www.meawisdom.com/ #PsychologicallyRichLife #PsychologicalRichness #ChipConley #MidlifeChrysalis #MidlifeReinvention #Curiosity #HealthyAging #LifelongLearning #GrowthMindset #MidlifePurpose #LifeAfter50 #LivingWithoutRegret #NewExperiences #MidlifeTransformation #Longevity

  3. 4d ago

    We’re Living Longer. Why Isn’t Society Ready? | David Sinclair

    The longevity revolution isn’t coming. We’re already living it, and we’re not ready. In this episode, David Sinclair of the International Longevity Centre joins Chip Conley to explore what longer lives mean for all of us and why society needs to catch up with a future that’s already here. In this conversation: Why the real longevity challenge isn’t living to 100, but adapting to longer lives todayWhy prevention needs to play a much bigger role in how we approach health and agingHow longer lives are changing the way we think about work, money, retirement, and our communitiesWhy purpose, connection, and staying engaged matter as much as staying healthyHow the wisdom we accumulate over a lifetime can be shared with the next generation Watch the full episode for a fresh perspective on longevity and what it will take to make our longer lives healthier, more purposeful, and more connected.  Timestamps: (03:13) Why Society Isn’t Ready for Longer Lives (04:47) Why We Keep Ignoring the Aging Crisis (07:13) What Governments Must Do About Longevity (10:14) Why Prevention Should Come First (12:01) Building Cities for Longer, Healthier Lives (15:48) The Economics of an Aging Population (18:09) Rethinking Life for the 100 Year Age (20:39) Can Human Lifespan Keep Increasing? (26:13) Living Longer Isn’t Enough (27:18) Why Purpose Matters as We Age (31:21) David Sinclair on the Other David Sinclair (34:53) Who Is Getting Longevity Policy Right? (37:53) The Responsibility to Pass on Wisdom (41:04) The Business Opportunity of Longevity  Learn more about MEA at ⁠https://www.meawisdom.com/ #DavidSinclair #InternationalLongevityCentre #Longevity #AgingSociety #HealthyAging #LongevityEconomy #AgingPopulation #FutureOfAging #PurposefulAging #100YearLife #LongevityPolicy #FutureOfRetirement #PreventiveHealth #AgeFriendlyCities #LifelongLearning

  4. Aug 28

    From Achievement to Fulfillment: Building Your Life 3.0 | Seth Streeter

    Success can look impressive on the outside and still leave you feeling like something is missing.Seth Streeter, co-founder of Mission Wealth, spent decades building a successful career while constantly pushing himself to achieve more. But after personal crisis, health struggles, and a major identity shift, he began questioning what success was really for. In this episode, Seth shares his journey from achievement to Life 3.0, a new chapter centered on fulfillment, purpose, and what truly makes us come alive. Key insights include: Achievement can become an identity. When worth is tied to productivity and success, stepping away can be harder than expected.Redefining success changes what matters. A fulfilling life requires looking beyond money, status, and conventional measures of achievement.Transformation requires letting go. Moving forward often means releasing old roles, habits, and ideas about who we need to be.Your values reveal what’s missing. Identifying what matters most can expose the gap between the life you’re living and the life you want. Tune in for an inspiring conversation about redefining success, finding what makes you come alive, and creating a more fulfilling next chapter.  Timestamps: (04:04) Seth’s origin story (09:12) The cost of relentless achievement (09:51) Building Mission Wealth (12:31) When life fell apart (15:39) Finding a new way forward (19:50) Wealth vs. fulfillment (23:16) Leaving the company he built (27:12) Finding purpose in Life 3.0 (29:30) What keeps people stuck in Life 2.0 (32:45) What makes you come alive? (33:39) Identifying your core values (36:01) Love, impact, and health (38:07) Building deeper human connection (40:12) Redefining success Learn more about MEA at ⁠https://www.meawisdom.com/#Life30 #RedefiningSuccess #MidlifeTransformation #MidlifeReinvention #PersonalGrowth #LifePurpose #Fulfillment #FindingPurpose #LifeTransitions #IdentityShift #MeaningfulLife #CoreValues #SelfDiscovery #MidlifeWisdom #SethStreeter

  5. Aug 26

    Could Living Together Be the Secret to Aging Better?

    Growing older is changing. Maybe the way we live should change with it. In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to later life: shared homes that combine independence, connection, and community. Drawing on MEA’s growing Golden Girls experiment, Chip shares: Why traditional senior living and aging in place don’t work for everyoneWhat MEA has learned from its first shared homes and Golden Girls retreatsWhy privacy, flexibility, and compromise are essential to making shared living workHow shared homes can grow into vibrant “distributed villages” built around friendship, learning, and common interestsHow this model could inspire new approaches to housing and community far beyond MEA Watch the full episode to discover a different way to think about home, community, and growing older. Timestamps: (00:00) Welcome to Wisdom Wednesday (01:39) Rethinking How We Live as We Age (05:05) The Golden Girls Shared Living Idea (07:05) Sage House and Chrysalis House (10:26) The Realities of Shared Living (12:51) Are You Ready to Live With Others? (14:46) Bringing the Concept to Other Communities (16:38) Creating a Distributed Village (19:09) The Long-Term Vision for MEA Homes (22:09) What About the Golden Guys? (23:05) How to Explore Golden Girls Living Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #WisdomWednesday #ModernElderAcademy #MEA #GoldenGirlsLiving #SharedLiving #AgingWell #HealthyAging #PositiveAging #SeniorLiving #CommunityLiving #LifeAfter55 #Midlife #Longevity #AgingInPlace

  6. Aug 24

    You Got Everything You Wanted. Now What? | Edward Sullivan

    What happens when you achieve the success you've worked for... and it still doesn't feel like enough? In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success. Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work and leadership, and what it really takes to build a meaningful life in the second half of adulthood. Key insights include: Why success often creates unexpected emptinessHow AI is changing leadership and workThe role curiosity plays in personal growthWhy self-care is a leadership skillA powerful question that can help shape your next decade If you're navigating midlife, rethinking your priorities, or wondering what comes after achievement, this conversation offers practical wisdom for building a more meaningful future. Watch now and discover what might be waiting on the other side of success. Timestamps: (01:14) Meet Edward Sullivan (02:34) What Makes a Great Coach? (04:54) AI Anxiety and Burnout (06:44) Tuning the Instrument (08:37) Coaching Young Founders (09:42) Wisdom and Age Diversity (12:49) Building Intergenerational Teams (17:16) Curiosity Before Advice (20:11) Midlife and the Happiness Curve (22:37) Right-Sizing Expectations (24:32) Why Success Can Feel Empty (28:56) The Power of Small Experiments (32:17) Designing a Meaningful Life (35:43) Advice for New Coaches (37:57) The Business of Coaching (40:16) Finding Your Coaching Niche (41:32) A Lesson Learned the Hard Way (43:41) What Now Workshop (44:18) Building a Career Crescendo (45:38) Closing Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ Workshop with MEA in March 2027: https://www.meawisdom.com/workshop/what-now-finding-passion-and-purpose-after-a-big-success-march-2027/ #LifeAfterSuccess #WhatNow #PurposeAndMeaning #ExecutiveCoaching #LeadershipDevelopment #CareerTransition #PersonalGrowth #MidlifeTransition #SuccessfulButUnfulfilled #SelfDiscovery #MeaningfulLife #ModernElder #ChipConley #EdwardSullivan #VelocityCoaching

  7. Aug 21

    Follow the Energy, Not the Career Script | Arun Gupta

    Your job title tells people what you do. The problem you care about tells them who you are. Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life. Some of the ideas they explore: Why following your energy can lead you somewhere a career plan never couldHow becoming a beginner again can bring fresh energy to midlifeWhy learning, earning, and giving back can happen throughout our livesWhat younger generations can teach us about work and purposeWhy our most human strengths matter even more in the age of AI From leaving a 20-year career in venture capital to stepping into the vulnerability of teaching and public service, Arun shares why the next chapter doesn’t need to be mapped out before you begin it. Watch the full episode of The Midlife Chrysalis. Timestamps: (03:39) Arun Gupta’s Mission-Driven Journey (09:05) From India to Venture Capital (12:50) Why Careers Don’t Follow a Straight Path (16:28) What Gen Z Is Teaching Us (20:33) Rethinking Learn, Earn, and Return (22:33) Finding New Purpose Later in Life (25:07) What Makes a Great Mentor (29:24) Learning Across Generations (33:23) AI and the Future of Work (36:17) Building Human Capital in the AI Age (39:25) Arun’s Midlife Career Reinvention (43:46) What Problem Do You Care About? (47:24) Doing Good and Doing Well (49:00) Rebuilding Trust Through Interdependence Learn more about MEA at ⁠https://www.meawisdom.com/ #ArunGupta #ChipConley #MidlifeChrysalis #TheMissionGeneration #NobleReach #CareerReinvention #PurposeDrivenCareer #MidlifeCareer #FutureOfWork #IntergenerationalMentorship #LifelongLearning #AIAndWork #CareerPurpose #MeaningfulWork #SecondAct

  8. Aug 19

    How to Discover the Gift That’s Uniquely Yours?

    What if the thing that makes you different has been there all along, you just haven’t named it yet? In this Wisdom Wednesday, Chip Conley and Derek Gehl explore how to “excavate your essence” and uncover the unique gift that can guide your work, choices, and life. You’ll discover: How Airbnb uncovered “Belong Anywhere” by looking beyond what the company does to why it mattersA simple five-question exercise for getting beneath the obvious answersHow Chip discovered his gift as a “social alchemist” and used it to better understand his pathWhy other people and the right environment can help you see what’s difficult to uncover alone Your essence isn’t something you need to invent. It’s something you can uncover. Watch now and ask yourself: What gift can I offer? Timestamps: (00:00) Welcome to Wisdom Wednesday (01:45) How to Excavate Your Essence (02:04) What Makes You Different? (04:04) The Five Questions Exercise (04:59) How Airbnb Found Its Essence (06:28) What Gift Can You Offer? (08:00) Discovering Your Unique Gift (10:38) Let Your Essence Guide You (12:09) Why You Can’t Do This Alone (14:31) Make Space for an Epiphany (14:54) Try the Essence Exercise Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #MidlifeChrysalis #WisdomWednesday #ExcavateYourEssence #FindYourGift #MidlifePurpose #SelfDiscovery #ModernElderAcademy #MEA #PersonalGrowth #MidlifeWisdom #FindYourEssence #UniqueGifts #PeterDrucker #SocialAlchemist

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4.9
out of 5
76 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
    156
  • Rating
    Explicit
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis