The Midlife Chrysalis

Chip Conley
  • 4.9 (73)
  • 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

    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

  2. 4d ago

    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

  3. 6d ago

    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

  4. 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

  5. Jul 3

    The Biggest Myth We Believe About Aging | Dr. Michael Gurven

    Most of us have been taught that humans used to die young, aging means decline, and longevity is something only modern science can unlock. Anthropologist Dr. Michael Gurven offers a very different perspective. In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Gurven, author of Seven Decades, to explore what indigenous cultures can teach us about aging, health, purpose, and living well. Together, they discuss: Why humans often lived much longer than we assumeWhat traditional societies reveal about healthy aging and chronic diseaseWhy elders earned respect through purpose and contributionHow aging and menopause were sometimes seen as sources of freedom and powerWhy community, movement, and meaning matter more than we think This conversation challenged so many modern assumptions about aging, from the myth that humans used to die at 30 to the surprising ways traditional societies viewed elders, menopause, health, and purpose later in life. Timestamps: (03:32) Introduction to Seven Decades book (05:34) Why Humans Were Meant to Live Longer (08:30) Longevity Myths and Historical Lifespans (10:22) The Role of Elders in Human Evolution (12:38) Geronticide and Elder Care Traditions (15:17) Lessons from Indigenous Communities (17:58) What Modern Society Can Learn About Health (22:35) Why Retirement Is Unnatural (24:59) Midlife, Identity, and the U Curve (29:39) Workaholism and Personal Reflections (32:28) Midlife Needs Rituals and Rites of Passage (35:32) Menopause, Aging, and New Life Stages (38:32) Blue Zones and Indigenous Longevity (44:13) Wisdom Learned Through Midlife (48:24)Parenting, Identity, and Letting Go (50:30) Final Thoughts and Book Recommendation Learn more about MEA at ⁠https://www.meawisdom.com/ #Longevity #HealthyAging #HumanLongevity #Anthropology #IndigenousWisdom #AgingWell #MidlifeChrysalis #HealthyLifestyle #BlueZones #AncientHumans #HumanEvolution #AgingMyths #LongevitySecrets #PurposeAndAging #ModernAging

  6. Jul 1

    Stop Trying to Fit In: The Hidden Gift of Aging

    What if one of the greatest gifts of aging is finally caring less about fitting in? In this Wisdom Wednesday conversation, Chip Conley and Derek Gehl explore why growing older isn't just about gaining wisdom, but about gaining the freedom to become more fully yourself. Chip shares why authenticity becomes more important than achievement, how we shift from building a resume to building a legacy, and why embracing your quirks may be one of the healthiest forms of personal growth. In this episode, you'll learn: Why people-pleasing becomes less important with ageThe difference between being admired for what you do and who you areHow to identify the qualities you want to be remembered forWhy "getting weird" may actually be a sign of growth If you're ready to stop living by convention and start living more authentically, this conversation is for you. Watch now and discover what it means to become delightfully unhinged. Timestamps: (00:48) Becoming Delightfully Unhinged (02:20) Why We Love Eccentric Older People (04:18) Admiration Addiction and Authentic Success (06:30) Growing Older and Growing Whole (08:35) Admired for What You Do vs Who You Are (12:32) Curating Your Eulogy (15:30) Embracing Your Idiosyncrasies (17:00) Authenticity and Code Switching (17:39) How Different Cultures Define Weird (19:06) Michelle Obama and Authentic Choices (20:00) Jim Flaherty and Aging with Originality (21:16) Creativity and Delightful Weirdness (21:32) This Week’s Homework: Go Be Weird Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #PersonalGrowth #Authenticity #SelfDiscovery #AgingWell #LifeLessons #MidlifeTransformation #PurposeInLife #Wisdom #SelfAcceptance #MentalWellbeing #EmotionalHealth #ChipConley #ModernElder #MidlifeChrysalis

  7. Jun 29

    Can Your Mind Change How You Age? | Ellen Langer

    Aging may have less to do with your body than you think. In this fascinating conversation, Chip Conley talks with Harvard psychologist Ellen Langer, whose groundbreaking research has spent decades challenging what we think we know about aging, health, mindfulness, and human potential. Drawing on stories from her life and her famous Counterclockwise study, Ellen explains why many of the limits we accept as part of growing older may be more flexible than we realize. In this episode, you'll discover: Why mindfulness begins with simply noticingWhat Ellen's Counterclockwise study revealed about agingHow our beliefs influence memory, health, and performanceWhy uncertainty can make life richer, not scarierHow questioning assumptions can open new possibilities at any age Warm, thought-provoking, and often surprisingly funny, this conversation will leave you looking at aging, and life itself, in a completely different way. Listen now and find out why Ellen believes we're capable of far more than we think. Timestamps: (01:37) What Mindfulness Really Means (04:48) Why We Live Mindlessly (08:16) Is Mindlessness More Efficient? (11:46) Mindfulness and Aging (13:06) Memory Loss or Something Else? (17:26) The Counterclockwise Study (20:00) Testing Mind-Body Unity (24:02) Can You Turn Back the Clock? (25:07) Learning New Skills at Any Age (27:45) Fixed Mindsets About Aging (28:50) Who Says So? (32:04) What Gets Better With Age? (36:03) Getting Comfortable in Your Own Skin (37:44) Will Ellen Ever Retire? (39:11) Ellen’s Core Life Lesson (40:33) The Story Behind Mind-Body Unity (43:24) Finding Opportunity in Adversity (45:25) Coming Full Circle to Mindfulness Learn more about MEA at ⁠https://www.meawisdom.com/ #EllenLanger #Mindfulness #HealthyAging #Longevity #AgingWell #PositiveAging #Psychology #Mindset #PersonalGrowth #MentalHealth #HarvardPsychology #SuccessfulAging #CounterclockwiseStudy #MidlifeChrysalis #ChipConley

  8. Jun 26

    Why We Spend Years Chasing Things We Don't Really Want | Alain de Botton

    You followed the rules, built a successful career, and checked the boxes you thought would make you happy. So why does something still feel missing? In this powerful conversation, bestselling author, philosopher, psychotherapist, and founder of The School of Life, Alain de Botton joins Chip Conley to explore what midlife teaches us about happiness, relationships, purpose, and becoming more fully ourselves. In this episode, you'll learn: Why status, success, and achievement often fail to deliver lasting fulfillmentHow heartbreak, loneliness, and setbacks can become sources of wisdomWhy friendship becomes more valuable as we get olderThe hidden reason so many relationships struggle and what better love requiresWhy self-knowledge is the foundation of a meaningful life Filled with insight, honesty, and practical wisdom, this conversation offers a refreshing perspective on aging, growth, and what truly matters. Watch now and discover why midlife may not be a crisis at all. It may be the beginning of your most authentic chapter. Timestamps: (02:00) Meet Alain de Botton (03:25) Philosophy vs Psychotherapy (05:59) The Origin of The School of Life (07:42) Knowledge vs Wisdom (11:33) Status Anxiety Explained (14:48) Why Midlife Changes Us (17:12) What Gets Better After 50 (19:10) Friendship and Heartbreak (21:23) Modern Love and Relationships (24:52) The Art of Travel (27:14) Travel as Self-Discovery (30:15) Places That Feed the Soul (31:24) Childhood and Curiosity (33:46) Solving Our Parents' Problems (34:35) Becoming a Psychotherapist at 50 (37:33) A Wisdom Bumper Sticker (40:40) Know Yourself (41:16) Learning New Things Later in Life (43:17) Final Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #PersonalGrowth #SelfKnowledge #Happiness #SuccessMindset #LifePurpose #EmotionalIntelligence #Wisdom #MeaningOfLife #StatusAnxiety #Relationships #Psychology #TheSchoolOfLife #AlainDeBotton #MidlifeCrisis

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4.9
out of 5
73 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
    133
  • Rating
    Clean
  • Copyright
    © Chip Conley
  • Show Website
    The Midlife Chrysalis

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