EducationSelf-Improvement

The Midlife Chrysalis

Chip Conley

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.

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34 episodes
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Avg 39 min
English

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S1 · E169
Yesterday · 44 min
He Died 11 Years Ago. Their Relationship Never Ended. | Lucy Kalanithi
Eleven years after losing her husband, the pain has changed. The love hasn’t. Dr. Lucy Kalanithi, physician and widow of Paul Kalanithi, author of When Breath Becomes Air, joins Chip Conley for a deeply personal conversation about grief, caregiving, uncertainty, and building a meaningful life after profound loss. Drawing on her experience as a wife, mother, caregiver, and doctor, Lucy shares what more than a decade of living with grief has taught her: Why death doesn’t necessarily end our relationship with someone we love How grief changes over time, even when the love remains Why caregivers need permission to ask for help and protect themselves How losing Paul changed the way she cares for patients and their families How to live with uncertainty when there are no clear answers Watch the full episode for a moving perspective on love, loss, and what it means to keep living when life changes forever. Timestamps: (04:14) Lucy Kalanithi’s Story (05:20) When Breath Becomes Air (06:40) Staying Connected After Loss (13:20) How Grief Changes Over Time (14:18) Advice for Living With Grief (16:04) How Loss Changed Her as a Doctor (18:44) The Reality of Caregiving (21:06) What Caregivers Really Need (23:45) Living With Uncertainty (27:33) Finding Acceptance in the Unknown (31:42) Serenity, Courage, and Wisdom (35:05) Raising a Child After Loss (38:13) Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ Be part of the conversation at the End Well Conference in Los Angeles on November 12, where Lucy Kalanithi and Chip Conley will take the stage to explore how we can live, care, and face life’s biggest transitions with greater meaning. Learn more and get tickets: https://endwellproject.org/end-well-2026/ #LucyKalanithi #PaulKalanithi #WhenBreathBecomesAir #Grief #LifeAfterLoss #LoveAfterLoss #Bereavement #Caregiving #LivingWithLoss #Mortality #Uncertainty #Acceptance #MidlifeWisdom #ChipConley #MidlifeChrysalis
S1 · E168
Friday · 35 min
Why Life Can Get Harder and Happier After 50 | Jonathan Rauch
Jonathan Rauch had reached the top of his career, yet each year he felt less satisfied. Then came the loss of his parents, his job, and a startup he had tried to build. To his surprise, his sense of contentment began to grow. Rauch is a journalist and the author of The Happiness Curve, The Constitution of Knowledge, and Cross Purposes. He joins Chip Conley to explore what his personal experience and research reveal about getting older, and why the future looks more troubling for younger adults. In this conversation: Why achievement does not always bring the happiness we expect Why life satisfaction often rises after 50, even through setbacks Why young adults’ loss of hope concerns Rauch Why free speech alone is not enough to establish what is true How wisdom helps us navigate conflict, and why it can be taught Watch for an honest, thought-provoking conversation about happiness, truth, and the value of staying curious throughout life. Timestamps: 03:49 Seeing what others miss06:59 The midlife happiness curve10:31 Why life can get better after 5012:21 Why young adults are losing hope15:49 How society knows what is true20:57 Wisdom in an age of disinformation24:53 Advice for the next generation26:34 Staying curious as we age Learn more about MEA at ⁠https://www.meawisdom.com/ #JonathanRauch #ChipConley #TheHappinessCurve #HappinessAfter50 #MidlifeHappiness #AgingWell #LifeSatisfaction #YoungAdultHappiness #Wisdom #Truth #Disinformation #ConstitutionOfKnowledge #ModernElder #MidlifeWisdom #Curiosity
S1 · E167
Wednesday · 27 min
The Hardest Leadership Lesson: Let Someone Else Be the Hero
Being the person who saves the day feels good. But letting someone else do it can make you a better leader. MEA founder Chip Conley joins Derek Gehl to talk about one of the hardest changes in his career: moving from hero to coach. Chip shares how he is learning to step back, trust his team, and make room for others to lead. Why having all the answers can hold your team back How asking questions helps others grow into leaders Why purpose matters as an organization gets bigger How to build something that can thrive without you What leadership can become in your next chapter Watch the full episode to hear Chip’s candid take on letting go and leading with greater wisdom. Timestamps: (00:00) Intro (02:30) From Hero to Coach (04:39) Bill George and Purpose Driven Leadership (07:40) Learning to Lead Together (10:06) Servant Leadership (11:20) Finding Meaning in Work (12:31) Leadership as a Practice (14:19) Building Culture Across an Organization (16:09) Building an Organization That Thrives Without You (18:25) Your Next Chapter of Leadership (22:48) The Bill George Workshop (25:17) A Leadership Experiment Learn more about MEA at ⁠https://www.meawisdom.com/ Listen to the podcast episode with Bill George, CEO of Medtronic: https://youtu.be/M9PuSyubTB0 #ChipConley #Leadership #LeadershipDevelopment #WiseLeadership #MidlifeLeadership #ServantLeadership #FounderLeadership #LeadershipCoaching #Mentorship #PurposeDrivenLeadership #OrganizationalCulture #BillGeorge #ModernElder #WisdomWednesdays #TeamLeadership
S1 · E174
September 28 · 35 min
What Changes When You Finally Let Go of Control? | Thomas DeLong
Success can look impressive on a résumé and still leave you wondering who you really are. At 76, Harvard Business School professor and former Morgan Stanley executive Thomas DeLong is rethinking some of the biggest lessons he has learned about leadership, courage, relationships, and success. In this conversation with Chip Conley, he reflects on: Why letting go of control can deepen relationships How to move from image management to essence Why vulnerability is a powerful form of courage How inherited success scripts can define the path we follow Why later life is about investing wisdom, not just retiring From family and leadership to identity and aging, DeLong shares the hard-earned lessons that have changed how he sees himself and the people around him. Watch now for a deeply personal conversation about letting go, finding courage, and defining success on your own terms. Timestamps: (02:40) Letting Go of Control (04:31) Building Closer Relationships (07:20) Vulnerability With His Daughters (09:35) Courage and Self-Doubt (13:00) Courageous Life Decisions (16:45) From Image to Essence (20:44) Changing Leadership at Morgan Stanley (23:38) The Parable of the Sadhu (26:04) Measuring a Meaningful Life (30:58) Investing Wisdom in the Next Decade (34:00) Sing Loudly and in Harmony (36:10) Breaking Free From the Success Script (38:36) A New Definition of Success Learn more about MEA at ⁠https://www.meawisdom.com/ Watch Chip’s Soul Biography, created by filmmaker Nic Askew: MEAWisdom.com/Soul #ThomasDeLong #ChipConley #MidlifeChrysalis #HarvardBusinessSchool #Leadership #RedefiningSuccess #PersonalGrowth #SelfAcceptance #Vulnerability #Courage #LettingGo #MidlifeWisdom #AuthenticLeadership #LifeLessons #HealthyAging
S1 · E164
September 25 · 51 min
Let Life Lead: A Different Way to Navigate Midlife | Nic Askew
Sometimes the most powerful way forward begins by doing less. Filmmaker Nic Askew has spent more than two decades capturing what happens when people stop performing and simply allow themselves to be seen. Through his Soul Biographies, he has discovered a different way of approaching connection, identity, and life itself. In this episode, Nic explores: Why “starting with nothing” can reveal what effort cannot How stillness creates space for the soul rather than the ego to lead Why doing less can help us truly see and connect with others How letting go of control can reveal what comes next in lifeIt’s a fascinating conversation about soul, human connection, and learning to let life lead. Watch the full episode and discover the power of starting with nothing. Timestamps: (03:24) Discovering Filmmaking at Midlife (04:18) Picking Up a Camera (08:54) A Calling Out of Nowhere (12:14) Starting With Nothing (16:53) The Soul Biographies (17:32) Speaking From Ego vs. Soul (19:17) Letting Life Lead (23:48) Stillness Before Action (28:13) Truly Seeing Others (31:07) Deepening Connection (37:34) Filming the MEA Community (42:13) Seeing Beyond the Persona (46:51) Nic’s Life Wisdom The Soul of MEA, the link is: MEAWisdom.com/Soul Learn more about MEA at ⁠https://www.meawisdom.com/ #NicAskew⁠ ⁠#SoulBiographies⁠ ⁠#Midlife⁠ ⁠#MidlifeTransformation⁠ ⁠#PersonalGrowth⁠ ⁠#SelfDiscovery⁠ ⁠#AuthenticLiving⁠ ⁠#LifePurpose⁠ ⁠#HumanConnection⁠ ⁠#Stillness⁠ ⁠#SoulWork⁠ ⁠#MidlifeWisdom⁠ ⁠#LetLifeLead⁠ ⁠#Presence⁠ ⁠#MEA
S1 · E163
September 23 · 24 min
Be Useful, Not Youthful: The Secret to Aging Well
At some point in midlife, achievement stops being enough. The titles matter less, the phone may stop ringing, and the question becomes: where does your value come from now? In this episode of Wisdom Wednesday, MEA founder Chip Conley joins Derek Gehl to explore the shift from achievement and admiration toward generativity, usefulness, and helping others grow. Key insights include: Why feeling invisible doesn’t mean becoming irrelevant How to move from “sage on the stage” to “guide on the side” Why being useful matters more than staying youthful How becoming “good soil” helps other people and future generations flourish Why doing good without getting credit can be one of the most meaningful forms of contribution Watch the full episode to discover a different way to think about purpose, relevance, and growing older. Timestamps: (00:00) Welcome to Wisdom Wednesday (00:41) The Sacred Pause (03:48) Becoming Good Soil (05:43) Regenerating Soil and Soul (07:55) Shifting Roles in Midlife (08:30) From Sage to Guide (10:21) Generativity vs. Stagnation (13:47) Staying Generative After Retirement (15:20) Feeling Invisible in Midlife (15:59) What You Have to Offer (18:55) Be Useful, Not Youthful (19:15) Finding a New Role (21:19) Crystallized Intelligence (22:26) Give Without Getting Credit (23:55) Letting Others Grow (25:12) Quiet Generosity Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #MidlifeChrysalis #ModernElderAcademy #WisdomWednesday #Generativity #MidlifePurpose #LifeAfter50 #AgingWell #MidlifeWisdom #CrystallizedIntelligence #PurposeAfter50 #Mentorship #MidlifeTransition #SacredPause #GoodSoil
S1 · E162
September 21 · 56 min
Can Your Beliefs Actually Change How You Age? | Shawn Achor
We’re taught to expect decline as we get older. But the science tells a far more hopeful story. In this episode, bestselling author and positive psychology expert Shawn Achor joins us to explore how our beliefs can shape the way we age. Drawing from his new book, The Power of Beliefs, groundbreaking research, and his own midlife experience, Shawn reveals why getting older can bring new opportunities for growth, meaning, happiness, and wisdom. You’ll discover: How beliefs about aging can influence our physical and cognitive outcomes Why midlife doesn’t have to mark the beginning of decline How negative expectations can become powerful nocebo effects Why life can become more meaningful even as our priorities change How “neuroscaping” can reshape the stories we tell about our lives From stepping away from career success to rediscovering what truly matters, Shawn offers a compelling new perspective on aging and the potential that remains ahead. Watch now to discover why your beliefs about getting older may matter more than you think. Timestamps: (03:04) Finding Joy and Wonder in Family Life (04:54) Rethinking Potential in Midlife (09:07) How Fatherhood Changed His Priorities (12:47) Feeling Replaced and Rediscovering Meaning (15:20) How Divinity School Reshaped His Faith (20:16) The Power of Beliefs (24:18) The Nocebo Effect (25:38) How Beliefs About Aging Shape Outcomes (29:09) Optimism and the U-Curve of Happiness (34:11) Why Meaning Can Grow With Age (38:51) Neuroscaping Your Memories (45:59) Turning Possibility Into Reality (47:21) Why Happiness Leads to Success (50:58) Growing Wiser With Age Learn more about MEA at ⁠https://www.meawisdom.com/ #ShawnAchor #PositivePsychology #PowerOfBeliefs #Midlife #HealthyAging #PsychologyOfAging #Happiness #Mindset #AgingWell #PersonalGrowth #MeaningAndPurpose #Optimism #Neuroscaping #MidlifeGrowth #SuccessfulAging
S1 · E161
September 18 · 50 min
He Spent 10 Years Filming the World’s Oldest People | Sam Green
What can the world’s oldest people teach us about time, aging, and being alive? Academy Award nominated filmmaker Sam Green spent 10 years filming people who held the title of the world’s oldest living person. His documentary The Oldest Person in the World began as a curiosity but became a deeply personal exploration of mortality, connection, and how we use the time we have. In this episode, Sam shares: What life really looks like at 115 and what seems to matter most The surprising traits he noticed among the world’s oldest people How a serious illness transformed his own relationship with time Why accepting life’s uncertainty can change how we live His advice for staying connected, creative, and engaged as we age This conversation isn’t about defeating aging. It’s about paying attention to the life you have while you have it. Watch now for a fascinating perspective on longevity, mortality, and what makes a life meaningful. Timestamps: (05:13) The Oldest Person in the World (08:14) Longevity vs. Mortality (10:21) What Centenarians Have in Common (13:20) What Life Is Like at 115 (15:12) Meeting the World’s Oldest People (17:49) What Helps Us Live Longer (19:36) A Life-Changing Diagnosis (23:22) The Film Distribution Challenge (28:02) Making a Living in Documentary Film (30:19) Becoming a Filmmaker (32:33) Advice for Aspiring Filmmakers (36:01) Favorite Documentaries (38:07) Would You Live to 115? (39:50) The Origins of MEA (42:14) Make Younger Friends Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: ⁠https://www.meawisdom.com/celebrate Learn more about MEA at ⁠https://www.meawisdom.com/ #SamGreen #TheOldestPersonInTheWorld #Longevity #Aging #HealthyAging #Mortality #LivingTo115 #DocumentaryFilm #DocumentaryFilmmaking #Midlife #LifeLessons #MeaningfulLife #SundanceFilmFestival #Wisdom #MEA
S1 · E160
September 16 · 22 min
Why Birthdays Matter More as We Get Older
Why do we celebrate birthdays as kids, then slowly stop celebrating ourselves as we get older? In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl for a conversation about birthdays, aging, and why life’s milestones deserve more attention, not less. After decades of marking his own milestone birthdays in memorable ways, Chip shares why celebration has become even more meaningful as he’s grown older and faced his own mortality. Key insights from the episode: Birthdays are more than a number. They can become rituals that help us recognize where we’ve been and who we’re becoming. Turning 50 deserves to be celebrated. Midlife is a major transition and an opportunity to consciously mark a new chapter. Celebration doesn’t have to mean being the center of attention. It can be an experience shared with the people who matter most. One of the gifts of aging is wisdom. Instead of focusing only on getting older, we can recognize everything we’ve learned along the way. Life gives us more reasons to celebrate than we notice. Careers, relationships, transitions, achievements, and even unexpected milestones can all be worth honoring. Tune in for a refreshing conversation about aging, wisdom, and why celebrating life may matter more than ever as we get older. Timestamps: (00:00) Introduction (00:25) Celebrating Life Through Milestone Birthdays (05:10) Why We Stop Celebrating as We Age (07:17) Why Turning 50 Deserves a Ritual (09:11) Resistance to Celebrating Yourself (10:26) Reframing Birthdays as Celebrations of Life (12:14) Why Adults Stop Celebrating Birthdays (15:11) Making Your Birthday a Gift to Others (15:54) Celebrating the Wisdom That Comes With Age (18:43) What Else Should We Celebrate? (19:41) Experiment of the Week Check out Chip's Celebrating Life's Wisdom Oct 25-29 2026 workshop: https://www.meawisdom.com/celebrate Learn more about MEA at ⁠https://www.meawisdom.com/ #ChipConley #WisdomWednesday #MidlifeWisdom #CelebrateLife #CelebratingAging #MilestoneBirthday #Turning50 #LifeAfter50 #MidlifeMilestones #PositiveAging #WisdomAndAging #BirthdayCelebration #MidlifeTransition #RitesOfPassage #AgingWithPurpose
S1 · E159
September 14 · 48 min
Surfing at 87, Writing at 91: James Flaherty’s Rules for Life
At 91, James Flaherty isn’t slowing down. He’s still writing, creating, learning, and planning what comes next. A former advertising executive, entrepreneur, innkeeper, and author who wrote five books in his 80s, James joins Chip Conley to share what nine decades of living have taught him about aging well and staying fully engaged with life. In this episode, James shares: Stay useful, not youthful. Growing older brings experience and wisdom that can be put to work for others. Always have a reason to wake up. Purpose, goals, and new projects keep life moving forward at every age. Never stop learning. Curiosity opens new doors and gives you opportunities to keep growing and discovering new parts of yourself. Stay connected. Community, friendship, and being present for others become even more important as we age. Help someone today. Small acts of kindness and service can make someone else’s life better while giving greater meaning to your own. Watch the full episode for an inspiring perspective on longevity, purpose, and making every stage of life count. Timestamps: (00:00) Meet James Flaherty (03:06) Writing Five Books in His 80s (05:21) James’ Early Life and Career (08:20) Moving to Argentina (10:30) A 47-Year Partnership (15:36) Caring for a Partner With Dementia (18:37) What Gets Better With Age (21:16) The Wisdom That Comes With Age (23:33) James’ Longevity Recipe (26:57) How to Find Your Purpose (28:39) Four Pathways to Purpose (33:45) Advice for Younger Generations (34:39) Help Someone Today (38:12) What James Still Wants to Do Learn more about MEA at ⁠https://www.meawisdom.com/ #HealthyAging #Longevity #Purpose #AgingWell #ActiveAging #Midlife #LifeAfter50 #PositiveAging #HealthyLongevity #PersonalGrowth #Wisdom #FindingPurpose #SuccessfulAging #JamesFlaherty #ChipConley
S1 · E158
September 11 · 49 min
From Role to Soul: Who Are You Without What You Do? | Connie Zweig
Aging isn’t just about getting older. It’s about discovering who you are when the roles that once defined you begin to fall away. In this episode, Chip Conley sits down with Connie Zweig, author of The Inner Work of Age, to explore the deeper psychological and spiritual work of midlife and beyond. Connie shares what it takes to move from simply growing old to becoming an elder, including: Moving from role to soul: Why identity built around achievement and productivity may need to loosen as we age. Meeting your shadow: How the parts of ourselves we ignore can surface during major life transitions and shape our choices without us realizing it. Listening to the unlived life: Why buried desires, abandoned paths, and old patterns often reappear at midlife. Learning to let go: How releasing outdated roles, beliefs, relationships, and attachments can make space for a new stage of life. Accepting impermanence: What Connie has learned in her 70s about mortality, control, self-reflection, and living more consciously. This is a thoughtful conversation about aging not as decline, but as a profound inner transition. Watch now and discover what it means to move from role to soul. Timestamps: (02:40) Growing and Aging Throughout Life (08:17) Letting Go of Roles and Identities (10:02) Moving From Doing to Being (17:28) What Is Shadow Work? (20:05) From Role to Soul (23:17) The Unlived Life and Midlife Crisis (29:14) The Inner Ageist (31:58) The Chrysalis of Midlife (34:41) Facing Death and Mortality (39:37) What Rumi Can Teach Us (43:35) Wisdom for Younger Generations (45:40) Impermanence, Control, and Conscious Living Learn more about MEA at ⁠https://www.meawisdom.com/ #Midlife #ConsciousAging #ShadowWork #MidlifeTransformation #HealthyAging #InnerWork #CarlJung #RoleToSoul #MidlifeCrisis #PersonalGrowth #SelfReflection #AgingWell #SecondHalfOfLife #UnlivedLife #ConnieZweig
S1 · E157
September 9 · 22 min
You Can’t Rush Grief: Learning to Feel What We’ve Lost
Some losses hit harder than we ever expect, and grief doesn’t follow our timeline. In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the unexpected death of his beloved dog Jamie and what the experience has taught him about grief, love, and loss. Key insights from the episode: Grief comes in waves. It can surface as sadness, anger, exhaustion, or simply the need for space. You can’t rush grief. Searching for meaning too quickly can keep us from actually feeling what we’ve lost. Grief reveals what we love. The depth of our grief often reflects the depth of the connection. Some losses go unacknowledged. Pets, relationships, careers, health, and unrealized expectations can leave grief we never fully allowed ourselves to feel. Tune in for an honest and moving conversation about the losses we carry, the emotions we can’t control, and why there is no shortcut through grief. Watch the full episode now. Timestamps: (00:00) Welcome to Wisdom Wednesday (02:10) Remembering Jamie (07:05) How Grief Comes in Waves (10:40) The Losses We Don’t Talk About (11:44) Why Unexpected Loss Hits Harder (12:54) Finding Ways to Cope With Grief (13:55) The Danger of Spiritual Bypass (18:53) You Can’t Force Grief (19:16) Grief, Anger, and Boundaries (20:30) Letting Emotions Pass Through (22:07) An Experiment for Unprocessed Grief (24:34) Grieving the Losses of Cancer (26:03) Closing Thoughts Learn more about MEA at ⁠https://www.meawisdom.com/ #Grief #GriefAndLoss #CopingWithGrief #PetLoss #UnprocessedGrief #GrievingProcess #ChipConley #MidlifeChrysalis #EmotionalHealing #SpiritualBypass #LifeAfterLoss #UnexpectedLoss #GriefJourney #MidlifeWisdom #MEA
S1 · E156
September 7 · 43 min
What Happens After You Achieve Your Biggest Dream? | Paul Harris
What happens when the identity you've spent your entire life building suddenly disappears? Former South African international cricketer Paul Harris reached the highest level of his sport, but retiring at just 33 forced him into an even bigger challenge: discovering who he was beyond cricket. In this powerful conversation, Paul shares the emotional reality of life after professional sports and the lessons that helped him build a meaningful second chapter. In this episode, you'll learn: Why major life transitions often trigger an identity crisis The hidden mental health challenges many high achievers face The three principles that helped Paul rebuild his confidence, purpose, and career Why the people you surround yourself with can shape your future Why "Outwork Everybody" became the foundation of his success Paul's journey proves that losing one identity doesn't mean losing yourself. Sometimes the end of one chapter is the beginning of a more meaningful one. If you enjoyed this episode, please like, subscribe, and share it with someone who could benefit from Paul's story. Timestamps: (02:46) Meet Paul Harris (03:44) Early Life and Playing Cricket (08:36) What is a Spinner? (10:45) Baseball vs. Cricket (11:22) Why Cricket Never Caught in the US (13:15) Why He Retired At 33 (15:00) Losing His Identity After Cricket (18:24) Life After Fame (21:14) Starting Over At 40 (22:22) Why Retired Athletes Struggle (27:01) Advice For Major Life Transitions (31:30) What Midlife Means To Him (33:35) Wisdom Bumper Sticker Learn more about MEA at ⁠https://www.meawisdom.com/ #PaulHarris #LifeAfterSuccess #IdentityCrisis #ProfessionalAthlete #LifeAfterSports #CareerTransition #FindingPurpose #SecondChapter #MentalHealth #HighPerformance #Resilience #PersonalGrowth #SuccessMindset #Cricket #MidlifeChrysalis
S1 · E155
September 4 · 49 min
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
S1 · E154
September 2 · 24 min
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
S1 · E153
August 31 · 45 min
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 today Why prevention needs to play a much bigger role in how we approach health and aging How longer lives are changing the way we think about work, money, retirement, and our communities Why purpose, connection, and staying engaged matter as much as staying healthy How 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
S1 · E152
August 28 · 47 min
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
S1 · E151
August 26 · 23 min
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 everyone What MEA has learned from its first shared homes and Golden Girls retreats Why privacy, flexibility, and compromise are essential to making shared living work How shared homes can grow into vibrant “distributed villages” built around friendship, learning, and common interests How 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
S1 · E150
August 24 · 50 min
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 emptiness How AI is changing leadership and work The role curiosity plays in personal growth Why self-care is a leadership skill A 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
S1 · E149
August 21 · 49 min
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 could How becoming a beginner again can bring fresh energy to midlife Why learning, earning, and giving back can happen throughout our lives What younger generations can teach us about work and purpose Why 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

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