The Midlife Chrysalis

Episoder

• 
  How to Discover the Gift That’s Uniquely Yours? 19.08.2026 15min

  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 aloneYour 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 ExerciseLearn more about MEA at ⁠https://www.meawisdom.com/#ChipConley #MidlifeChrysalis #WisdomWednesday #ExcavateYourEssence #FindYourGift #MidlifePurpose #SelfDiscovery #ModernElderAcademy #MEA #PersonalGrowth #MidlifeWisdom #FindYourEssence #UniqueGifts #PeterDrucker #SocialAlchemist
• 
  How to Talk to People You Profoundly Disagree With | Shamil Idriss 17.08.2026 45min

  How do you find common ground with someone you profoundly disagree with?At a time when political, religious, and cultural divisions seem deeper than ever, peacebuilder Shamil Idriss, CEO of Search for Common Ground, shares what decades of bringing people together have taught him about trust, conflict, and human connection.In this conversation with Chip Conley, Shamil explores:Why being heard and respected matters more than being agreed withHow building trust before a crisis can bridge even deep dividesWhy curiosity is more powerful than judgmentHow taking just one meaningful action can restore hopeWhy today’s breakdown may ultimately lead to breakthroughFrom global conflicts to disagreements in our own communities, Shamil offers a hopeful reminder that our futures are interconnected, and that each of us can help build common ground.Watch now to discover how connection can begin, even when we disagree.Timestamps:(03:50) Meet Shamil Idriss(04:55) The Beginning of Peacebuilding Journey(08:48) Inside the UN Alliance of Civilizations(11:02) Why Our Futures Are Connected(15:07) How to Build Common Ground(19:40) What Can We Do Together?(21:39) How Trust Is Built Across Differences(24:07) Being Heard Matters More Than Agreement(26:19) Curiosity Instead of Judgment(29:10) Why Peacebuilding Is Harder Today(32:00) The Power of Doing One Thing(36:48) How to Hold On to Hope(40:38) A Lifetime of LessonsLearn more about MEA at ⁠https://www.meawisdom.com/#ShamilIdriss #SearchForCommonGround #Peacebuilding #CommonGround #PoliticalPolarization #ConflictResolution #BridgingDivides #BuildingTrust #CulturalCuriosity #HumanConnection #Dialogue #MidlifeWisdom #Ubuntu #SocialCohesion #ChipConley
• 
  Why Retirement Is the Wrong Goal | Ken Dychtwald 14.08.2026 47min

  Midlife isn't the beginning of the end. For more than 50 years, Dr. Ken Dychtwald, psychologist, bestselling author, and founder of Age Wave, has studied what it really means to grow older.In this conversation, he explains why midlife isn't the beginning of the end, but the start of one of life's most meaningful transformations.In this episode, you'll discover:Why midlife is a time of growth, not declineThe powerful idea of "middle essence" and how it changes the way we think about agingWhy retirement may be one of today's biggest mythsHow purpose becomes even more important as we get olderThe simple advice Ken believes can help anyone build a richer, more meaningful lifeIf you're navigating midlife or wondering what's possible in the years ahead, this conversation will change the way you think about aging.Enjoyed this episode? Subscribe, leave a review, and share it with someone who needs this message.Timestamps:(03:39) Ken Dychtwald's Early Journey(08:31) The Exercise That Changed His Career(10:42) Predicting the Age Wave(14:55) Why Ageism Persists(16:34) Midlife Is a Chrysalis(18:05) The Case for "Middle Essence"(20:55) Why Society Doesn't Support Midlife(25:41) Ken's Midlife Lessons(29:56) Why He Never Retired(31:00) The Untapped Purpose of Older Adults(33:10) The Two Books Everyone Should Read(34:54) Advice for Chip Conley(36:38) Why Deep Questions Matter(37:22) The Future of Midlife(40:01) Think Bigger Than Yourself(42:18) Love, Mentors, and Lifelong RelationshipsLearn more about MEA at ⁠https://www.meawisdom.com/#KenDychtwald #MidlifeTransformation #MiddleEssence #SecondHalfOfLife #PurposeAfter50 #AgeWave #Retirement #Ageism #PsychologyOfAging #HumanPotential #PersonalReinvention #ChipConley #Elderhood #Midlife #Purpose
• 
  Why Midlife Feels Stuck (And How to Break Free) 12.08.2026 23min

  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 ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#ChipConley #SocialEulogy #LivingFuneral #MidlifeChrysalis #WisdomWednesday #ModernElder #MeaningfulRelationships #HearYourEulogy #LeaveNothingUnsaid #HumanConnection #LifeLessons #Legacy #MidlifeWisdom #EmotionalWellbeing #RelationshipAdvice
• 
  How Psilocybin Can Change Your Life After 40 | Neil Markey 10.08.2026 55min

  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 ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#Psilocybin #Psychedelics #PsychedelicTherapy #MentalHealth #Midlife #MidlifeTransformation #PersonalGrowth #Healing #Meditation #SelfDiscovery #Wellness #Neuroplasticity #MentalWellbeing #BeckleyRetreats #TheMidlifeChrysalis
• 
  Your Brain Is Lying to You About Happiness | Dr. Laurie Santos 07.08.2026 45min

  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 lifeIf 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 ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#LaurieSantos #ChipConley #HappinessScience #PsychologyOfHappiness #PositivePsychology #Midlife #MidlifeChrysalis #Mindset #HealthyAging #Longevity #SocialConnection #PurposeInLife #Yale #HappinessResearch #LiveWell
• 
  Why High Achievers Still Feel Like Imposters 05.08.2026 25min

  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 lifeIf 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 SyndromeLearn more about MEA at ⁠https://www.meawisdom.com/#ImposterSyndrome #SelfDoubt #GrowthMindset #HighAchievers #CareerTransition #Midlife #PersonalGrowth #Mindset #Confidence #Vulnerability #FearOfFailure #ChipConley #ModernElderAcademy #MidlifeChrysalis #EmotionalIntelligence
• 
  The Biggest Lies We've Been Told About Aging | Ashton Applewhite 03.08.2026 46min

  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 lifeWatch 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 GrowthLearn more about MEA at ⁠https://www.meawisdom.com/#Aging #Ageism #HealthyAging #GrowingOlder #PositiveAging #Longevity #OlderAdults #Midlife #LifePurpose #PersonalGrowth #Psychology #Intergenerational #AgeDiversity #WellBeing #AshtonApplewhite
• 
  Why Your 70s Can Be Your Most Meaningful Years | Dr. Philip Pizzo 31.07.2026 49min

  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 WellLearn more about MEA at ⁠https://www.meawisdom.com/#PhilipPizzo #MidlifeChrysalis #PurposeAfterRetirement #SuccessfulAging #Longevity #StanfordDCI #LifeReinvention #HealthyAging #RetirementPurpose #SecondHalfOfLife #LifeTransitions #SpiritualGrowth #MeaningfulLife #CommunityAndConnection #AgingWell
• 
  Don't Save It for the Funeral: The Power of a Social Eulogy 29.07.2026 19min

  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 ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#ChipConley #SocialEulogy #LivingFuneral #MidlifeChrysalis #WisdomWednesday #ModernElder #MeaningfulRelationships #HearYourEulogy #LeaveNothingUnsaid #HumanConnection #LifeLessons #Legacy #MidlifeWisdom #EmotionalWellbeing #RelationshipAdvice
• 
  The Hero’s Journey: Crossing the Threshold from Stagnation to Generativity | Pat Whitty 27.07.2026 46min

  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 LifeLearn more about MEA at ⁠https://www.meawisdom.com/#CaminoDeSantiago #HealthyAging #Purpose #PersonalGrowth #Adventure #ActiveAging #LifeLessons #AgingWell #Midlife #Retirement #SelfDiscovery #Inspiration #Walking #SpiritualJourney #ChipConley
• 
  The Power of Play in Reinventing Your Life | Kristine Michie & JD Schramm 24.07.2026 45min

  Play isn't just for kids. It's one of the most powerful tools for navigating change, finding purpose, and becoming more fully yourself.In this episode of Midlife Chrysalis, Chip Conley sits down with Kristine Michie founder of the Playful Podcast, and JD Schramm, communication expert and former Stanford professor, to explore how play, storytelling, and authenticity can transform the way we approach midlife.What you'll discover:Why losing a job can become the beginning of your next chapter.How the need to impress others quietly shapes our identity.Why your experience and wisdom are your greatest competitive advantage.How play and human connection can be the antidote to an AI-driven world.What it truly means to become the person you're meant to be.If you're in the middle of a career transition, feeling the pressure to prove yourself, or wondering how to stay deeply human in an AI-driven world, this episode offers a refreshing roadmap for what comes next.Enjoy the episode, and don't forget to like, subscribe, and share it with someone who could use this message.Timestamps:(04:34) Kristine's Journey to Purpose(07:19) JD's Storytelling Career(08:56) Reinventing Yourself in Midlife(12:17) Finding Opportunity After Job Loss(16:09) The Pressure to Impress Others(18:09) Advice for Midlife Career Changes(20:54) Discovering Your Unique Strengths(24:04) The Power of Play and Story(26:16) Why Play Sparks Creativity(29:45) Play as the Antidote to AI(31:50) 10 Benefits of Play(34:54) Type 2 Fun and Growth(37:05) The Different Play Personalities(38:32) Wisdom Gained Through Life(39:24) Kristine's Life Lesson(40:30) JD's Advice on Becoming Yourself(41:18) Living a Life of Continuous GrowthLearn more about MEA at ⁠https://www.meawisdom.com/#MidlifeChrysalis #Midlife #CareerTransition #LifeTransitions #Authenticity #PersonalGrowth #ReinventYourself #PowerOfPlay #Storytelling #SelfDiscovery #Purpose #AI #HumanConnection #EmotionalWellbeing #MidlifeReinvention
• 
  Can AI Ever Be Wise? Knowledge vs. Human Experience 22.07.2026 21min

  Can AI really replace human wisdom? Or are we undervaluing the one thing machines will never have?In this Wisdom Wednesday, Chip Conley and Derek Gehl explore a powerful idea inspired by the Spanish language: there are two different ways of "knowing." One is knowledge anyone, including AI, can access. The other comes only through lived experience.In this conversation, you'll discover:Why AI can know facts but will never have real wisdom.The difference between knowing something and experiencing it.Why stories are more powerful than information alone.A simple habit to help you learn from your own life.How to trust your intuition with more confidence.As AI becomes part of everyday life, understanding the difference between knowledge and wisdom has never been more important.🎧 Watch now, and if you enjoy the episode, please like, subscribe, and share it with others.Timestamps:(00:00) Introduction(01:40) Two Ways of Knowing(05:14) What AI Can and Can't Know(08:31) Experience vs Information(10:01) Why Stories Matter(16:01) Turn Experience Into Wisdom(18:10) Everyone Has Wisdom(19:30) This Week's Reflection(20:03) Trusting Your IntuitionLearn more about MEA at ⁠https://www.meawisdom.com/#ArtificialIntelligence #HumanWisdom #AIvsHumans #LivedExperience #KnowledgeVsWisdom #Storytelling #Leadership #PersonalGrowth #CriticalThinking #FutureOfWork #EmotionalIntelligence #LifelongLearning #HumanPotential #Midlife #MidlifeChrysalis
• 
  The Science Behind a Better Midlife| Dr. Margie E. Lachman 20.07.2026 45min

  Midlife is far more hopeful and full of possibility than most of us have been led to believe.In this episode of The Midlife Chrysalis, Chip Conley talks with Dr. Margie E. Lachman, one of the world's leading experts on lifespan psychology, director of the landmark MIDUS study, and author of Prime Time. Drawing on decades of research, she shares why midlife is one of the most important stages of life and how the choices we make today shape our future health, happiness, and sense of purpose.In this conversation, you'll learn:Why midlife is the perfect time to reflect, reset, and growHow your mindset about aging can influence your health and longevityWhat the science says about feeling younger than your ageWhy mentoring others and finding purpose become more meaningful over timePractical ways to make the second half of life your best yetIf you're looking for a more positive, research backed perspective on aging, this episode is for you.Enjoy the conversation, and if you find it valuable, please like, subscribe, and share it with someone who could use a fresh perspective on midlife.Timestamps:(00:00) Intro(03:04) Margie's Personal Story(05:17) Why Midlife Gets a Bad Reputation(09:11) Seeing the Opportunity in Midlife(11:04) The Midlife Review(14:32) Midlife as a Hinge Point(16:19) Who You Are and Who You Want to Be(20:13) What Generativity Really Means(22:07) What Makes a Great Mentor(24:06) The MIDUS Study Explained(26:30) The Biggest Lessons About Midlife(28:05) The Power of Subjective Age(33:39) Why Americans Struggle More in Midlife(36:28) Do We Need Midlife Wisdom Schools?(38:42) Healthspan Over Lifespan(39:22) Stop and Smell the RosesLearn more about MEA at ⁠https://www.meawisdom.com/#Midlife #HealthyAging #SuccessfulAging #MidlifeResearch #PositiveAging #MargieLachman #Psychology #LifespanDevelopment #MidlifeMindset #AgingWell #Resilience #Purpose #Wellbeing #MidlifeWellbeing #MidlifeChrysalis
• 
  How to Build a Life You Don't Want to Retire From | Stephen Herman & Evelyn Neaman 17.07.2026 47min

  Retirement isn't the end of your career. It's the beginning of the life you've been preparing for.In this episode, filmmaker and former lawyer Stephen Herman and criminal justice reform leader Evelyn Neaman share the personal experiences that inspired them to rethink retirement and help others navigate this major life transition with purpose and confidence.Together, they explore:Why so many people struggle after retirement, even when they're financially prepared.How purpose, community, and meaningful work shape a happier next chapter.Why it's worth thinking about retirement long before you're ready to stop working.How trying something new in midlife can completely change the future.This conversation is full of practical wisdom for anyone wondering what comes next, whether retirement is years away or just around the corner.If you enjoyed this episode, please like, subscribe, and share it with someone who could use a fresh perspective on retirement and life's next chapter.Timestamps:(06:37) Welcome Stephen and Evelyn(07:49) Why Retirement Needs Planning(11:26) Purpose Community and Wellness(13:08) Building a New Career Together(15:58) Making a Film About Retirement(19:39) Advice for First Time Filmmakers(22:24) Why Retirement Conversations Matter(24:16) Planning Retirement Early(28:20) Fear of Uncertainty(30:01) The Value of Retirement Coaches(32:48) Redefining Retirement(36:50) Retirement and the Fear of Aging(39:06) Wisdom for a Meaningful Life(43:11) The Bumper Sticker That Says It AllLearn more about MEA at ⁠https://www.meawisdom.com/#RetirementPlanning #LifeAfterRetirement #PurposeAfterRetirement #SecondAct #RetirementPurpose #RetirementMindset #CareerTransition #LifeBeyondWork #RetireWithPurpose #RetirementAdvice #RetirementJourney #IdentityAfterRetirement #MeaningfulRetirement #StephenHerman #EvelynNeaman
• 
  What Your Future Self Wants You to Know About Life 15.07.2026 20min

  Have you ever wondered what your 80 year old self would tell you today?In this episode, Derek and Chip talk about aging, relationships, purpose, and the life lessons that only become clear with time. Through a powerful exercise imagining a conversation with his future self, Chip shares the insights that have reshaped how he thinks about success, love, health, and what truly matters.In this episode, you'll discover:Why talking to your future self can help you make better decisions today.The surprising relationship lesson that completely changed Chip's perspective on growing older.How a simple journaling exercise unlocked unexpected insights and self reflection.Why success, legacy, and achievement become less important than the people you grow with.How your priorities naturally evolve as you move through the second half of life.If you're navigating midlife, rethinking your priorities, or simply looking for a fresh perspective on what makes a meaningful life, this conversation is full of wisdom you won't want to miss.🎧 Watch the full episode and join the conversation.Timestamps:(00:00) Welcome(01:53) Talking to Your Elder Self(04:17) Lessons From Your Future Self(06:43) The Importance of Relationships(10:44) Leaving a Meaningful Legacy(11:44) Taking Better Care of Your Health(12:43) How to Do the Elder Self Exercise(15:33) What the Experience Felt Like(18:06) Applying the Lessons to Life(20:09) Building a Lasting Legacy(21:28) Final ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#FutureSelf #FutureSelfExercise #ChipConley #MidlifeChrysalis #MidlifeWisdom #GrowingOlder #LifeLessons #MeaningfulRelationships #PersonalLegacy #SelfReflection #Journaling #Purpose #HealthyAging #PersonalGrowth #SecondHalfOfLife
• 
  How Time Away Can Change Your Future | DJ DiDonna 13.07.2026 49min

  Burnout, career uncertainty, and midlife stuckness have become increasingly common, but stepping away may be the key to moving forward.In this episode, Chip Conley sits down with DJ DiDonna, Harvard Business School senior lecturer, entrepreneur, and author of Big Time Off. After reaching burnout while running his dream company, DJ took a four-month sabbatical that transformed his perspective on work, success, and life.In this conversation, DJ shares:Why burnout is often a sign that something needs to changeHow sabbaticals create space for clarity, growth, and reinventionThe role of travel, pilgrimage, and reflection in personal transformationWhy midlife is the perfect time to reassess your prioritiesPractical advice for planning a sabbatical, even if it feels out of reachIf you're feeling stuck, overwhelmed, or ready for a new chapter, this conversation offers a powerful reminder that sometimes the most important step forward is taking a step back.Listen now and discover the transformative power of time away.Timestamps:(01:47) Introduction & DJ’s New Book(02:53) Burnout That Led to a Sabbatical(04:42) The Freedom of Having No Structure(06:18) Why Pilgrimages Transform People(10:47) What Changed After Four Months Away(13:08) Sabbaticals Inside Organizations(16:20) Do Employees Leave After Sabbaticals?(20:40) How Sabbaticals Improve Retention(22:20) The Value of Floating Managers(24:20) Fear, Burnout & Quiet Quitting(25:51) Why Midlife Needs Sabbaticals(31:00) Creating Midlife Inflection Points(32:20) The Three Sabbatical Archetypes(35:30) How to Take a Successful Sabbatical(39:40) Planning for Sabbaticals Financially(41:10) Sabbaticals as Regret Insurance(42:40) Wisdom Bumper StickerLearn more about MEA at ⁠https://www.meawisdom.com/#Sabbatical #MidlifeReset #PersonalGrowth #CareerChange #BurnoutRecovery #Midlife #LifeTransition #SelfDiscovery #WorkLifeBalance #PurposeDrivenLife #PersonalDevelopment #CareerReinvention #TimeOff #ChipConley #MidlifeChrysalis
• 
  The Soul of Money: Why Life Gets Better After 50 | Lynne Twist & Sara Vetter 10.07.2026 57min

  Can your greatest purpose begin after 50?In this powerful conversation, Chip Conley sits down with Lynne Twist, bestselling author of The Soul of Money, and her longtime collaborator Sara Vetter to explore purpose, money, mentorship, and the surprising opportunities that come with midlife.In this episode, you'll learn:Why midlife can be the start of your most meaningful chapter.How a life-changing trip to the Amazon transformed their paths.The mindset shift that can completely change your relationship with money.Why great partnerships are built on trust, honesty, and shared purpose.How joy and gratitude can shape a richer, more fulfilling life.Enjoyed this conversation? Like, subscribe, and share it with a friend. Then tell us in the comments: Has midlife changed your perspective on purpose, money, or what truly matters?Timestamps:(05:12) How Lynn and Sara Became Partners(12:02) Sara's Life-Changing Experience at 50(15:02) The Secret to a Lasting Partnership(18:08) Navigating Conflict with Honesty(20:45) Why the Pachamama Alliance Matters(27:11) Ayahuasca, Healing, and the Amazon(31:52) Why Midlife Can Change Your Life(37:52) Lynn's Calling at Age 50(43:45) The Soul of Money Explained(48:07) How to Transform Your Money Mindset(53:16) Life Lessons to Live ByLearn more about MEA at ⁠https://www.meawisdom.com/#LynneTwist #SaraVetter #ChipConley #Midlife #Purpose #TheSoulOfMoney #MoneyMindset #PersonalGrowth #LifeAfter50 #MeaningfulLife #MidlifeTransformation #SelfDiscovery #ConsciousLiving #AgingWell #PachamamaAlliance
• 
  How Wise People Handle Uncertainty 08.07.2026 23min

  Uncertainty is everywhere, from economic shifts and AI disruption to health challenges and major life transitions. The question isn't how to eliminate uncertainty, but how to navigate it with confidence.In this Wisdom Wednesday episode, Chip Conley and Derek Gehl explore practical ways to stay grounded when life feels unpredictable. Drawing from his experiences as an entrepreneur and his ongoing cancer journey, Chip shares the tools that have helped him face uncertainty with greater resilience, clarity, and purpose.In this episode, you'll learn:Why uncertainty is a normal part of lifeThe connection between anxiety, uncertainty, and powerlessnessHow to focus on what you can controlWhy intuition and wisdom matter most during difficult timesA simple exercise for reducing stress and making better decisionsListen now, and if you enjoy the episode, be sure to subscribe, leave a review, and share it with a friend.Timestamps:(00:00) Introduction(01:28) How to Navigate Uncertainty(04:14) Reducing Uncertainty Through Questions(06:42) Powerlessness and Agency(09:24) Lessons from Business Crises(11:18) Cancer, Denial, and Taking Action(13:22) Living in the Present Moment(14:32) Letting Go of Control(17:41) Key Lessons About Uncertainty(19:33) The Serenity Prayer and Wisdom(20:27) Building Confidence in Decisions(21:40) The Anxiety Balance Sheet Exercise(23:10) Worst Case vs Best Case Thinking(24:02) Final ThoughtsLearn more about MEA at ⁠https://www.meawisdom.com/#Uncertainty #Anxiety #MentalHealth #PersonalGrowth #WisdomWednesday #ChipConley #Resilience #SelfImprovement #LifeLessons #Mindset #EmotionalIntelligence #DecisionMaking #StressManagement #PersonalDevelopment #Midlife
• 
  The Skills That Will Matter Most in the AI Era | Chris Shipley & Scott Barry Kaufman 06.07.2026 45min

  AI is changing the way we work, but the skills that matter most are still deeply human.In this episode of The Midlife Chrysalis, Chip Conley is joined by Chris Shipley, technology visionary and leadership expert, and Scott Barry Kaufman, psychologist and bestselling author, for a thoughtful conversation about leadership, purpose, and human potential in the age of AI.Together, they explore why the future belongs to leaders who combine technology with wisdom, curiosity, and genuine human connection.In this episode, you'll discover:Why human skills will become even more valuable as AI evolvesHow leaders can reduce fear and build trust during times of changeWhy wisdom may be your greatest advantage in the futureHow different generations can learn from each otherWhy having a clear vision for your future self can change your lifeWhether you're leading a team, planning your next career move, or simply wondering what the future of work will look like, this conversation offers practical ideas and a hopeful perspective.Watch now and discover why the future belongs to leaders who never stop growing.Timestamps:(00:00) Intro(00:42) Introducing Chris Shipley & Scott Barry Kaufman(02:07) Leading For Tomorrow(05:53) The Future Of Human-Centered Leadership(07:11) What Would Maslow Think About AI?(08:56) Leading Through AI Uncertainty(11:24) Easing AI Anxiety At Work(14:13) What Makes People Feel They Matter(16:50) Best Lessons From The Book(22:39) Midlife In Silicon Valley(26:52) Becoming An Integrator In Midlife(28:33) Bridging The Generational Gap(35:10) Wisdom For Your Younger Self(39:27) Three Key TakeawaysLearn more about MEA at ⁠https://www.meawisdom.com/#AILeadership #HumanLeadership #FutureOfLeadership #FutureOfWork #LeadershipSkills #HumanPotential #ScottBarryKaufman #ChrisShipley #ChipConley #AIAnxiety #LeadershipDevelopment #HumanCenteredLeadership #Wisdom #EmotionalIntelligence #MidlifeChrysalis