The Midlife Chrysalis

Chip Conley
  • 4.9 (74)
  • 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. 13h ago

    Can AI Ever Be Wise? Knowledge vs. Human Experience

    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 Intuition Learn more about MEA at ⁠https://www.meawisdom.com/ #ArtificialIntelligence #HumanWisdom #AIvsHumans #LivedExperience #KnowledgeVsWisdom #Storytelling #Leadership #PersonalGrowth #CriticalThinking #FutureOfWork #EmotionalIntelligence #LifelongLearning #HumanPotential #Midlife #MidlifeChrysalis

  2. 2d ago

    The Science Behind a Better Midlife| Dr. Margie E. Lachman

    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 yet If 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 Roses Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #HealthyAging #SuccessfulAging #MidlifeResearch #PositiveAging #MargieLachman #Psychology #LifespanDevelopment #MidlifeMindset #AgingWell #Resilience #Purpose #Wellbeing #MidlifeWellbeing #MidlifeChrysalis

  3. 5d ago

    How to Build a Life You Don't Want to Retire From | Stephen Herman & Evelyn Neaman

    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 All Learn more about MEA at ⁠https://www.meawisdom.com/ #RetirementPlanning #LifeAfterRetirement #PurposeAfterRetirement #SecondAct #RetirementPurpose #RetirementMindset #CareerTransition #LifeBeyondWork #RetireWithPurpose #RetirementAdvice #RetirementJourney #IdentityAfterRetirement #MeaningfulRetirement #StephenHerman #EvelynNeaman

  4. Jul 15

    What Your Future Self Wants You to Know About Life

    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 Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #FutureSelf #FutureSelfExercise #ChipConley #MidlifeChrysalis #MidlifeWisdom #GrowingOlder #LifeLessons #MeaningfulRelationships #PersonalLegacy #SelfReflection #Journaling #Purpose #HealthyAging #PersonalGrowth #SecondHalfOfLife

  5. Jul 13

    How Time Away Can Change Your Future | DJ DiDonna

    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 reach If 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 Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #Sabbatical #MidlifeReset #PersonalGrowth #CareerChange #BurnoutRecovery #Midlife #LifeTransition #SelfDiscovery #WorkLifeBalance #PurposeDrivenLife #PersonalDevelopment #CareerReinvention #TimeOff #ChipConley #MidlifeChrysalis

  6. Jul 10

    The Soul of Money: Why Life Gets Better After 50 | Lynne Twist & Sara Vetter

    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 By Learn more about MEA at ⁠https://www.meawisdom.com/ #LynneTwist #SaraVetter #ChipConley #Midlife #Purpose #TheSoulOfMoney #MoneyMindset #PersonalGrowth #LifeAfter50 #MeaningfulLife #MidlifeTransformation #SelfDiscovery #ConsciousLiving #AgingWell #PachamamaAlliance

  7. Jul 8

    How Wise People Handle Uncertainty

    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 decisions Listen 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 Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #Uncertainty #Anxiety #MentalHealth #PersonalGrowth #WisdomWednesday #ChipConley #Resilience #SelfImprovement #LifeLessons #Mindset #EmotionalIntelligence #DecisionMaking #StressManagement #PersonalDevelopment #Midlife

  8. Jul 6

    The Skills That Will Matter Most in the AI Era | Chris Shipley & Scott Barry Kaufman

    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 life Whether 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 Takeaways Learn more about MEA at ⁠https://www.meawisdom.com/ #AILeadership #HumanLeadership #FutureOfLeadership #FutureOfWork #LeadershipSkills #HumanPotential #ScottBarryKaufman #ChrisShipley #ChipConley #AIAnxiety #LeadershipDevelopment #HumanCenteredLeadership #Wisdom #EmotionalIntelligence #MidlifeChrysalis

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4.9
out of 5
74 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
    137
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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