What if midlife isn’t a crisis, but your most creative chapter yet?

In this inspiring and deeply personal episode, bestselling author and entrepreneur Seth Godin shares how he’s reinvented his life through purpose-driven work, disciplined freedom, and the belief that life itself is a series of art projects.

We explore why the “dip” is a crucial part of growth, how to walk away from success when it no longer serves you, and what it really means to build a legacy. Seth also opens up about aging, identity, and choosing meaning over momentum.

It’s a conversation full of wisdom, honesty, and practical insight for anyone navigating change. Subscribe for more episodes that help you reimagine your next chapter!

Timestamps:

00:00 Intro

01:16 How Seth and Chip first met at Stanford

02:49 Writing their first book together

03:53 Jay Conrad Levinson as a modern elder

07:01 Writing over 150 books

08:31 Understanding The Dip and its midlife parallels

12:28 Seth’s two “Dip” examples

14:13 Chip’s hotel dip and decision making

17:27 Creativity, resilience, and entrepreneurship after 50

19:36 Not being in high school anymore & insulating yourself

22:49 Midlife crisis or chrysalis?

27:25 Alt MBA, The Carbon Almanac, and collaborative creation

32:03 Rebranding midlife and self-image as we age

35:28 Things that got better with aging

37:54 Seth’s perspective on retirement & legacy

41:16 Seth’s next project

42:42 The future of the U.S. and generational change

46:28 A bumper sticker of wisdom

48:14 The importance of the origin story

Learn more about MEA at https://www.meawisdom.com/

#SethGodinInterview #MidlifeChrysalis #StanfordStories #TheDipBook #PortfolioLife #ModernElderAcademy #CarbonAlmanacProject #AltMBAJourney #RebrandingMidlife #CreativeAging #WisdomInMidlife #OpportunityCostLesson #EntrepreneurAfter50 #LifeAsArtProject #TeachingLegacy

At 40, Hoda Kotb’s world fell apart—cancer, divorce, and the dream of having children slipping away. But what came next wasn’t the end. It was a beginning.

In this amazing episode, Hoda opens up about surviving breast cancer, finding the courage to adopt at 52, and learning that her 50s would become the most meaningful years of her life. She shares raw moments, unexpected joy, and the wisdom that only comes from starting over.

If you're navigating change or wondering if it's too late to begin again, this episode will speak straight to your heart. Subscribe to Midlife Chrysalis and join our community for more stories that prove the second half of life can be the best half.

Timestamps:

00:00 Intro

01:23 Growing Up in an Immigrant Family

03:25 Childhood in Nigeria and Egypt

05:49 Rejection, Resilience, and Unexpected Opportunities

08:27 A Tumultuous Early 40s: Marriage, Cancer & Change

14:14 Aging On-Air and Thriving in Her 50s

17:26 Adoption at 52 and the Joy of Motherhood

23:32 Love & Relationships Later in Life

28:59 Stepping Away from the Today Show

32:51 Starting a New Business at 60

34:39 Gratitude for Her Mom

36:22 Lessons from Her 60s: Be a Beginner Again

41:26 Hoda’s Wisdom Bumper Sticker

44:05 Closing Reflections

Learn more about MEA at https://www.meawisdom.com/

#HodaKotb #MidlifeChrysalis #WomenOver50 #BreastCancerSurvivor #MidlifeTransformation #ReinventionAfter50 #AdoptionStory #LifeAfterCancer #StartingOverAt50 #InspirationalWomen #PersonalGrowthJourney #LateBloomerSuccess #CareerChangeAfter50 #FindingPurposeInMidlife #NeverTooLate

What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna shares how his midlife crisis became a chrysalis—from collapsing under the weight of outward success to rebuilding a life rooted in meaning, connection, and emotional resilience.

He shares the moment he almost gave up, the books and mentors that helped him begin again, and why real leadership starts with healing yourself. If you're navigating uncertainty or chasing purpose after 40, this is your roadmap. Subscribe for more conversations that honour the complexity—and beauty—of becoming whole.

Timestamps:

00:00 Intro

00:51 Greeting and introduction

02:06 Jerry’s background & career journey

09:36 Fundamentally being broken

12:33 The crash of 2001 and Grand Canyon awakening

15:35 Post-9/11 breakdown and decision to change

18:41 The power of asking “How am I complicit?”

21:41 The pursuit of wealth and inner emptiness

25:57 Childhood trauma and the need to be seen

28:31 The transformation: from ego to true self

33:31 Becoming Buddhist business coach

37:57 Lessons from modern elders: Pema, Parker, Sharon

44:56 What gets better with age

47:10 Midlife wisdom and personal integration

51:34 The ability to enjoy bitter sweetness

52:50 Why do we need midlife wisdom schools

54:37 Collective healing and “you’re not alone”

56:10 Bumper sticker of wisdom

Learn more about MEA at https://www.meawisdom.com/

#MidlifeTransformation #JerryColonna #CEOCoach #EmotionalResilience #MidlifeAwakening #MentalHealthMatters #LeadershipWisdom #SpiritualGrowth #BurnoutRecovery #Psychoanalysis #BusinessAndSpirituality #RebootYourLife #ModernElders #LifeAfterSuccess #YoureNotAlone

What if midlife isn’t a crisis—but a chance to grow, heal, and start fresh? In this episode, Michael Franti shares how he transformed personal pain into purpose, why letting go of old stories changed his life, and how music helped him reconnect with himself and others.

Michael opens up about fatherhood, breaking free from emotional patterns, and the daily work of staying present in a distracted world. From his earliest songwriting days to his biggest transformations offstage, he reveals what it really takes to live with heart and intention. This episode is full of truth, warmth, and perspective for anyone ready to evolve.

Timestamps:

00:00 Intro

01:17 Maturing Through Mistakes

03:07 Impactful Midlife Transitions

06:03 AIDS Crisis & The Power of Sharing Stories

10:40 Success in His 50s & Roll of Wisdom

13:09 Creating from Emotion & Collaboration

18:06 Musical Genres & Identity Challenges

21:09 Learning to Play Guitar at 30

25:55 Moments with Bono and Childhood Trauma

34:16 Emotionally Unavailable Adoptive Mother

39:39 Overcoming Phone Addiction

43:17 Creating Deep Family Relationships

44:55 How His Dad Changed After a Stroke

48:26 Break Up with Everything You Don’t Need

51:47 Live Performance

55:33 Letting Go of Old Stories

Learn more about MEA at ⁠MEAWisdom.com

#MichaelFranti #MidlifeTransformation #PersonalGrowth #EmotionalHealing #FatherhoodJourney #LettingGo #LiveWithHeart #MindfulLiving #MusicAsMedicine #BreakTheCycle #StorytellingMatters #LifeAfter50 #HealingThroughMusic #IntentionalLiving #PresenceOverPerfection #SpiritualAwakening #NewBeginnings

What if the most powerful transformation of your life came after the titles, the heartbreak, and the noise? In this deeply moving episode, Maria Shriver opens up about rediscovering her identity beyond the Kennedy legacy, confronting the emptiness behind external success, and finally giving herself permission to become whole.

From her Catholic upbringing and complicated relationship with ambition, to the raw honesty of her poetry and spiritual healing, Maria shares how she moved through loss, betrayal, and public scrutiny—and came out the other side free, grounded, and fully herself.

If you're navigating your own midlife reinvention, craving deeper purpose, or learning to let go of old roles, this conversation will stay with you long after it ends.

Timestamps:

00:00 Intro

00:34 Who is Maria Shriver?

02:18 Faith Journey & Early Influence

05:20 Self-Discovery & Wholeness

07:44 Poetry & Embracing a Feminine Side

09:40 Finding Out Who You Really Are

15:06 The Poem “Connecting the Dots”

19:27 Messy Midlife & Reframing Aging

22:11 The Poem “Chaos” & Coming Out of Mess

30:14 Redefining Purpose, Love, and Legacy

32:21 Vulnerability as a Superpower

38:21 Embracing Freedom & Your True Self

41:05 Living Fully on Your Own Terms

44:48 What is Moral Beauty?

47:57 Evolving & Aging as a Gift

56:20 Final Wisdom

Learn more about MEA at MEAWisdom.com

#MariaShriver #MidlifeTransformation #Reinvention #SpiritualGrowth #FindingYourself #WomenEmpowerment #HealingJourney #EmotionalHealing #LettingGo #PoetryHealing #LegacyBeyondFame #VulnerabilityIsStrength #RedefiningSuccess #MoralBeauty #PersonalGrowth

Welcome to the very first episode of The Midlife Chrysalis!

Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, but a powerful chrysalis for transformation.

He shares his own wild journey and reveals why your 40s, 50s, and beyond can be the most meaningful years of your life. Plus, get a sneak peek at upcoming guests like Maria Shriver, Brian Chesky, Gavin Newsom, and more.

If you're ready to reinvent yourself and thrive in midlife, this is your new go-to podcast.

Timestamps:

00:00 Welcome to The Midlife Chrysalis

00:40 My Journey from Crisis to Chrysalis

01:24 Midlife as Time of Major Transition

02:15 Why This Podcast Matters

02:24 Upcoming Guests

03:08 An Invitation to Join the Journey

Learn more about MEA at ⁠MEAWisdom.com

#MidlifeTransformation #ReinventYourLife #ModernElder #MidlifeJourney #AgingWithPurpose #MidlifeMotivation #LifeAfter40 #LifeAfter50 #SecondActSuccess #MidlifeReinvention #PurposefulLiving #LongevityMindset #ChipConley #UCurveOfHappiness #MidlifeWisdom

What if hitting rock bottom was the best thing that ever happened to you?

In this raw and inspiring conversation, Rich Roll, a former addict turned world-class endurance athlete, shares how he rebuilt his life from scratch, facing failure, financial ruin, and identity loss to find real purpose.

With brutal honesty, he opens up about his addiction, fatherhood, marriage, legacy, and the heavy cost of chasing approval. If you're feeling stuck, burned out, or unsure what comes next, this conversation just might change how you see your own story.

Timestamps:

00:00 Introduction

01:13 Spine Surgery and Recovery

03:02 Losing Identity and Facing Stillness

05:47 Interviewing Master Interviewers

07:17 Life Begins at 40 & Rejecting the Race

11:06 How to Know You’re on the Right Track

13:42 Performance vs. Presence

15:25 Addiction, Achievement, and the Roots of Disconnection

19:49 The Midlife Chrysalis at Age 39

24:29 The Support of His Wife Julie

26:04 Lessons from Rich’s Midlife Chrysalis

32:14 From Blog to Writing a Book

38:10 Launching the Podcast & Relocating to Hawaii

42:27 Gaining Momentum

43:50 Financial Struggles and Family Impact

48:14 What Makes Rich Roll’s Podcast Different

51:58 The Importance of Genuine Curiosity

54:25 The Power of Vulnerability in Conversation

56:31 Rethinking Success and Slowing Down

01:01:46 Legacy, Family, and Showing Up

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeTransformation #RichRoll #SpineSurgeryRecovery #SobrietyJourney #PurposeInMidlife #EnduranceAthlete #AddictionRecovery #MidlifeReinvention #PersonalGrowth #PodcastLife #EmotionalResilience #LifeAfter40 #LegacyWork #AuthenticLiving #ModernElder

What does it really take to start over at 69?

In this inspiring episode, Whole Foods founder John Mackey shares how psychedelics, purpose, and love reshaped his path after selling to Amazon.From ego death to building Love Life wellness centers, he opens up about business regrets, spiritual breakthroughs, and midlife transformation. You'll learn how conscious capitalism evolves with age—and why love might be the ultimate business strategy.

Subscribe for more honest conversations about midlife renewal, purpose-driven living, and personal reinvention.

Timestamps:

00:00 Intro

00:27 Meet John Mackey

01:27 Psychedelics, Ego Death, and Food as Purpose

07:44 Love, Breakups, and Big Business Shifts

08:37 Austin in the '70s and Building Whole Foods

10:40 Advice to His Younger Self

12:34 From Atheism to Spiritual Adventure

14:36 What Is Conscious Capitalism?

17:15 How Whole Foods Revolutionized Grocery Stores

19:28 Learning to Communicate with Kindness

21:46 Selling Whole Foods to Amazon

28:17 Why He Finally Left Whole Foods

29:25 Healing Journey Through Plant Medicine

31:28 What Is Love Life?

37:56 Psychodelics as Therapeutic Method

40:21 Challenges and Financial Realities

43:21 Longevity Myths and What Actually Works

47:49 Redefining Retirement with Purpose

49:54 What He’d Regret Not Doing

52:09 Wisdom Bumper Sticker

55:33 Final Reflections

Learn more about MEA at ⁠https://www.meawisdom.com/

#JohnMackey #WholeFoods #ConsciousCapitalism #MidlifeTransformation #LongevityTips #PlantMedicine #PsychedelicHealing #PurposeDrivenLife #HolisticHealth #LoveLifeWellness #SpiritualGrowth #EntrepreneurMindset #ChipConley #FoundersJourney #ReinventYourself

What if your so-called “midlife crisis” was actually a doorway to reinvention?

In this powerful conversation, Burning Man CEO Marian Goodell joins Chip Conley to explore how the radical spirit of Burning Man offers surprising lessons on aging, identity, leadership, and legacy. From embracing impermanence to finding purpose without a script, this episode is a deep dive into how midlife can be your most creative and meaningful chapter yet.

Timestamps:

00:00 Intro

00:40 Chips Connection to Burning Man

04:43 What Burning Man Really Is

07:01 How Burning Man Became a Global Movement

08:47 The Core Principles That Guide Everything

11:13 Radical Self-Expression and Creating Without Expectation

13:38 Why Burning Man Attracts People in Midlife Transition

16:43 Loss, Legacy, and What We Leave Behind

21:46 Lessons from Larry Harvey as a Modern Elder

25:05 What She Learned as a Burning Man’s CEO

33:00 What Is Fly Ranch and Why It Matters

36:28 Fly Ranch Like Burning Man’s Feminine Side

39:24 Three Tips for Burning Man First-Timers

42:14 Burning the Man and Temple Rituals

47:22 The Healing Power of Ritual

50:08 Why MEA Resonates with Burners

53:40 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#BurningMan #MidlifeCrisis #MidlifeTransformation #MarianGoodell #BurningMan2025 #PersonalGrowth #ReinventionAfter40 #MidlifeAwakening #LifeAfter50 #SpiritualJourney #BurningManExperience #RadicalSelfExpression #MidlifeChrysalis #ChipConley #PurposeInMidlife

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?

In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.

What happens when a successful actor—and the son of a Hollywood legend—hits midlife and starts asking deeper questions?In this powerful episode, Scott Eastwood opens up about building his own identity beyond Clint Eastwood’s shadow, what 40+ films have taught him, and why he’s now prioritizing purpose over fame. He reflects on masculinity, mentorship, mistakes, and what it really means to grow wiser with age.Feeling your own shift? Subscribe to The Midlife Chrysalis and explore Modern Elder Academy’s workshops designed to help you thrive in midlife and beyond.

Timestamps:00:00 Intro00:41 Chip’s Relationship With His Dad 08:28 A Prolific Film Career09:38 Working with Clint Eastwood10:51 Carving His Own Path13:54 New Projects & Genre Exploration15:52 Masculinity in Modern Culture18:09 Growing & Maturing as a Man19:26 Questioning & Redefining Midlife21:32 Childhood Dreams & Creative Shifts24:05 Aging, Directing & Creative Control27:1 Time, Regret & Following Your Gut31:51 The Outpost Movie & Hyperbaric Healing35:07 Real Wellness, Not Wellness Trends37:16 Life Lessons & Emotional Maturity39:44 How Scott Hopes to Be Remembered41:31 Lessons from Mom & Dad43:20 Having Mentors & Becoming One44:13 Scott’s Wisdom Bumper Sticker49:13 Healing a Father-Son Relationship

Learn more about MEA at ⁠https://www.meawisdom.com/

#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut

What happens when one of the most thoughtful voices in public life hits a wall?

In this deeply personal conversation, Krista Tippett opens up about burnout, walking away from success, and rediscovering joy in midlife. From letting go of exhaustion to falling in love again, she shares the hard-won wisdom that’s reshaping how she lives, works, and loves. It’s a moving reminder that it’s never too late to begin again, so don’t miss this one.

Subscribe for more powerful conversations that spark reflection, reinvention, and real change in midlife.

Timestamps:

00:00 Welcome and Setup

00:46 Introducing Lee and the Unique Cast of Guests

01:52 What Makes a Great Interviewer?

06:12 Interviewing John O’Donohue

09:57 Thresholds and Transitions

12:58 Krista’s Childhood and Upbringing in Oklahoma

17:40 The Bible as Her First Text of Imagination

20:00 Interviewing Richard Rohr and Men’s Spiritual Lives

23:36 Krista’s Midlife Reflections

27:06 Midlife Chrysalis and Personal Transformation

30:53 Building a Life Around Love and Friendship

35:36 What She’d Regret Not Doing

38:09 What Brings Joy Now

42:03 Defining Wisdom and Growing Wiser

46:26 Staying Grounded Through Rituals and Attention

51:43 Rethinking Retirement

54:29 The Aging Brain and Synthesizing Wisdom

57:46 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeWisdom

#OnBeing #KristaTippett #MidlifeTransformation #SpiritualGrowth #LifeAfter40 #InnerLife #FindingPurpose #EmotionalResilience #WomenOver40 #BecomingWise #SoulfulLiving #PersonalGrowthJourney #AgingWithGrace #DeepConversations

What if midlife isn’t a breakdown—but a breakthrough?

In this powerful conversation, world-renowned writer Pico Iyer shares the surprising lessons he’s learned from 50 years of friendship with the Dalai Lama, losing everything he owned, and finding stillness in the chaos. From walking away from success in New York to building a soulful life in Japan, Pico reveals how true freedom comes not from having more—but from letting go. This episode is a masterclass in finding purpose, inner peace, and meaning in the second half of life.

Timestamps:

00:00 Intro

01:13 Meet Pico Iyer

02:02 Why TED Keeps Inviting Pico Back

02:50 Pico’s favorite TED talk

04:04 Early Life Across Continents

05:17 What “Home” Really Means

07:21 Stillness and the Midlife Chrysalis

12:33 Moving from Park Avenue to Kyoto

15:31 The Value of Being an Expat

18:10 Inner Calm in a Chaotic World

22:31 Everyday Stillness Practices

29:24 A Lifetime with the Dalai Lama

37:34 Living in Absence of Answers

42:29 Pico’s Anticipated Regret

46:11 What Makes MEA So Special

50:47 Awe, Community, and Transformation

53:27 Pico’s Wisdom Bumper Sticker

56:27 Episode Key Takeaways

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #PicoIyer #ChipConley #MidlifeTransformation #ModernElder #Stillness #InnerWisdom #SpiritualGrowth #LifePurpose #DalaiLama #HomeAndSoul #ExpatLife #GratitudePractice #Resilience #MindfulLiving

What happens when a Harvard scholar, devoted Mormon, and mother of a child with Down syndrome begins to hear psychic messages—and decides to tell the truth no matter the cost?

In this powerful conversation, Martha Beck shares how leaving her religion, embracing polyamory, and facing her deepest fears led her to a life of radical integrity, joy, and healing.

If you’ve ever felt stuck, out of alignment, or afraid to be fully yourself—this episode will change how you see everything.

Timestamps:

00:00 Intro

00:56 Meet Martha Beck

03:02 Growing Up Mormon, Academic Journey, and Her Son’s Diagnosis

10:53 Leaving Mormon Church & Reframing Midlife

14:47 Losing Religion, Finding Soul, and Polyamory

19:20 Returning to True Nature Through Rebellion

21:23 Lessons from Her Son with Down Syndrome

27:10 Psycho-Neuro-Immunology & Integrity

30:58 Shaman Sickness & Becoming a Healer

33:24 A Simple Path to Inner Stillness

40:01 The Radical Power of Not Lying

41:43 How to Listen to Your Body’s Response

52:27 Martha’s Bumper Sticker Wisdom

Learn more about MEA at ⁠https://www.meawisdom.com/

#MarthaBeck #ChipConley #TheWayOfIntegrity #MidlifeTransformation #SpiritualAwakening #LeavingMormonism #DownSyndromeParenting #PolyamoryJourney #LifePurpose #InnerHealing #TrustYourself #ModernElder #SelfDiscovery #PsychicExperiences #AnxietyAwareness

What happens when a self-made billionaire steps away from the company she built and faces the big question: What’s next?

In this inspiring episode, the founder of Spanx opens up about her journey from door-to-door sales to creating a global brand, the emotional challenges of selling her company, and how she’s redefining success, purpose, and identity in midlife. It’s a raw and uplifting conversation about reinvention, intuition, and finding meaning beyond business.

Timestamps:

00:00 Intro

01:56 Family background and kids

03:47 Childhood struggles and early mindset shift

06:32 Discovering Wayne Dyer and self-growth

09:00 Letting go of law school plans

09:46 Intuition and coping mechanisms

13:25 Selling fax machines and rethinking her path

14:17 The idea for Spanx is born

18:40 Building Spanx and landing Neiman Marcus

22:37 Growing Spanx without advertising

25:30 Selling Spanx and facing an identity shift

31:51 Midlife change and grief

34:44 Creating Sneaks brand

43:54 Psychology behind the second venture

47:32 Perimenopause, health issues, and PMDD

50:19 Modern Elder Academy experience

53:37 Focusing on presence and meaning

55:42 Introverts, extroverts, and integration

58:17 Feminine energy as a superpower

59:42 Wisdom bumpersticker

1:02:26 Chip’s final thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

#SarahBlakely #Spanx #FemaleEntrepreneur #WomenInBusiness #EntrepreneurLife #BusinessSuccess #Motivation #Inspiration #FounderStory #StartupJourney #MindsetMatters #SuccessTips #BusinessAdvice #SelfMadeWoman #EntrepreneurMindset #ChipConley #MidlifeChrysalis

Author, speaker, and “Radiant Rebel” Karen Walrond joins Chip Conley for a warm, inspiring conversation on how to age with joy, live on your own terms, and keep your spark alive.

From growing up between Trinidad and the U.S., to leaving engineering and law for a creative life, Karen’s story is full of bold choices and unexpected turns. She shares cultural insights on aging, how to break free from the “success script,” and the seven playful experiments from her new book In Defense of Dabbling that prove it’s never too late to try something new.

Packed with heart, humor, and practical wisdom, this episode will leave you smiling and inspired to chase your own adventures.

Timestamps:

00:00 Intro

00:45 Introduction to Karen Walrond

01:58 Growing up & career journey

06:50 Midlife shift toward writing and creative work

11:38 Cultural perspectives on aging in Trinidad vs. the U.S.

16:55 Defining the “Radiant Rebellion”

19:14 Resisting societal scripts

23:06 Aging in non-white cultures

31:43 Collaboration with Brené Brown

36:12 Introducing In Defense of Dabbling

40:03 The 7 attributes of dabbling

44:08 Why trying new things matters as we age

50:42 Karen’s experience teaching at MEA workshops

53:11 Karen’s wisdom bumper sticker

57:10 Chips’s closing reflections on joy, culture, and lifelong learning

Learn more about MEA at ⁠https://www.meawisdom.com/

#AgingBoldly #MidlifeReinvention #RadiantRebellion #LifeOnYourOwnTerms #NeverTooLate #MidlifeTransformation #CuriosityAndPlay #JoyfulAging #BreakingFree #LiveFully #MidlifeMotivation #RedefiningSuccess #KeepYourSparkAlive #IntentionalLiving #TrySomethingNew

What if aging wasn’t about slowing down—but about leveling up?

In this powerful conversation, Marc Freedman, founder of Encore.org (now CoGenerate), unpacks the surprising history of retirement, why communities like Sun City reshaped how we see aging, and how we can flip the script on what it means to grow older. From encore careers to intergenerational mentorship, Marc shows why midlife is no dead end—it’s a launchpad for purpose, impact, and connection.

If you’ve ever wondered how to thrive after 50, find meaning in your “second act,” or simply stay relevant in a rapidly changing world, this episode will change how you see the road ahead.

Timestamps:

00:00 Intro

00:39 Marc Freedman as Chip’s “modern elder”

02:46 How aging became feared, not revered

04:26 Why older people are no longer revered

07:30 Rise of retirement communities

13:14 Why people question retirement as a goal

15:56 Marc’s personal view on retirement

18:36 The origins & evolution of CoGenerate

24:10 Why intergenerational connection matters

27:46 What CoGenerate does to help

31:52 Big policy ideas for the future

37:31 Tips for those nearing retirement

44:15 Upcoming workshop with Chip

48:47 Wisdom bumper sticker

50:51 How does Marc measure success

54:00 Wrapping up

Learn more about MEA at ⁠https://www.meawisdom.com/

#MarcFreedman #EncoreCareers #ModernElder #MidlifeReinvention #FindingPurpose #LifeAfterRetirement #GenerationalCollaboration #CrossGenerational #AgingWell #WisdomAtWork #EncoreOrg #CoGenerate #ModernElderAcademy #SecondActCareers #PurposeDrivenLife

What happens when one of America’s most celebrated pastors dares to question everything?

In this unfiltered conversation, Rob Bell, once dubbed the “punk rock pastor” and author of the explosive bestseller Love Wins, opens up about the controversy that made him Christianity’s most talked-about heretic, why he walked away from his megachurch at the height of fame, and how midlife pushed him to reinvent himself.

From faith and psychedelics to wisdom traditions, AI, and the art of living an unpigeonholable life, Rob’s journey is as provocative as it is inspiring. Whether you see him as a rebel, visionary, or outlaw, one thing’s clear: you won’t walk away from this episode thinking the same.

Timestamps:

00:00 Intro

00:35 Meet Rob Bell

02:08 Following a Calling & Evolving

05:16 Early Life & First Sermons

11:04 Starting Mars Hill Church

13:02 Performance Art Preaching

15:01 Controversy & Pushback

16:44 Rise to Time’s 100 Most Influential People

21:10 Leaving the Church & Midlife Transition

26:25 Reinventing in His 40s

29:58 Evolving Faith & Moving Beyond Doctrine

31:46 The Greatest Unlearning

35:00 Surfing, painting & daily rituals

38:15 Reconnecting with Spirituality

40:25 On Psychedelics & Temples

44:57 From Knowledge to Wisdom

51:16 Redefining Intelligence

54:56 Rob’s Wisdom Bumper Sticker

57:47 Closing Reflections

Chip shares key takeaways on creativity, freedom, and living beyond expectations.

Learn more about MEA at ⁠https://www.meawisdom.com/

#RobBell #MidlifeChrysalis #PunkRockPastor #LoveWins #SpiritualJourney #MidlifeTransitions #FindingPurpose #WisdomTraditions #SpiritualAwakening #FaithAndCreativity #LeavingReligion #SpiritualGrowth #Unpigeonholable #MidlifeSpirituality #CareerEvolution

How do you survive when the person you can’t live without begins to destroy you?

In this powerful episode of Midlife Chrysalis, Elizabeth Gilbert joins Chip Conley to share the raw story behind her new memoir, All the Way to the River. She opens up about walking alongside her partner through addiction and relapse, confronting her own patterns of codependency, and finding healing through recovery and surrender. It’s an honest, unfiltered look at love, loss, and what it really takes to stand on your own two feet.

Tune in now to hear Elizabeth Gilbert as you’ve never heard her before.

Timestamps:

00:00 Intro

00:40 Introduction to Elizabeth Gilbert

03:06 All the Way to the River book

06:06 Why it took 7 years to write

07:21 A forensic look at repeating patterns

10:36 Love vs. addiction in relationships

13:49 How Liz met Raya & their evolving bond

19:55 Confessing love during Raya’s illness

25:31 Grief, loss, and missing her friend

27:18 Writing in solitude & surrendering to truth

35:00 Surrender, recovery, and true powerlessness

41:21 Dark thoughts & God’s voice

45:15 What sex & love addiction means for Liz

51:36 12-step practices & six years of abstinence

54:35 Reflections on MEA and retreat power

58:22 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #ElizabethGilbert #AllTheWayToTheRiver #GriefJourney #AddictionRecovery #LoveAndLoss #Codependency #HealingFromTrauma #12StepRecovery #SexAndLoveAddiction #SpiritualGrowth #MemoirWriting #MidlifeWisdom #EmotionalSobriety #LifeLessons

What if everything you’ve been taught about happiness and success is upside down?

In this episode of Midlife Chrysalis, Chip Conley talks with Arthur Brooks, Harvard professor, bestselling author, and former French horn prodigy, about his remarkable journey from the concert stage to the world of behavioral science. Together, they unpack why strivers burn out, how our brains shift from fluid to crystallized intelligence, and the simple formula that can turn midlife from a crisis into a transformation.

Don’t miss this inspiring conversation. Listen now and start rethinking your own second curve.

Timestamps:

00:00 Intro

01:06 Arthur Brooks’ origins and family background

02:59 Religious upbringing and conversion to Catholicism

04:56 Navigating academia and faith in secular environments

07:08 Early music training and struggles to become the best

13:06 Striver mentality and American entrepreneurship DNA

16:41 Leaving music for economics and behavioral science

20:52 Imposter syndrome and skills learned from performance

22:33 Becoming CEO of the American Enterprise Institute (AEI)

29:05 Burnout, midlife shift, and vital plane encounter

32:19 Plane encounter with a famous figure and reflection on decline

35:47 Realizing the need for a second curve

38:10 How we move from fluid to crystallized intelligence

42:43 Airbnb and the role of “modern elder” wisdom

45:02 Advice for shifting into careers built on crystallized intelligence

46:56 The danger of pride and Dante’s frozen Satan metaphor

49:40 Learning to want less: the secret to second-curve happiness

54:39 Editing life instead of accumulating - reverse bucket lists

55:55 Generativity, religion, and aging with meaning

57:16 Policy thoughts on midlife education and wisdom schools

1:01:59 Wisdom bumper sticker

1:05:28 Closing reflections from Chip

Learn more about MEA at ⁠https://www.meawisdom.com/

What happens when a world-famous photographer nearly loses everything — and turns it into a movement redefining aging?

In this powerful conversation, David Stewart shares his journey from shooting Vogue covers and working with Andy Warhol’s circle, to battling a life-threatening autoimmune disease that forced him to rethink everything. Out of crisis came transformation — and the creation of Ageist and Super Age, two platforms challenging stereotypes about aging and proving that purpose, health, and vitality don’t fade with time.

Watch now to discover how to stay healthier, live longer, and embrace your true greatness.

Timestamps:

00:00 Catching up: Manhattan, travel, and life during Covid

01:36 Childhood, school struggles, and proving people wrong

04:07 Studying engineering, switching to political science, and discovering photography

06:14 Declaring himself a photographer, early Vogue ad, and move to Paris

07:01 Life in New York: Andy Warhol’s scene, magazine covers, and big clients

08:02 Health crisis, autoimmune disease, and a year in hospital

10:00 Turning point: removing his spleen and changing lifestyle

11:01 The birth of Ageist: challenging age stereotypes in media and advertising

14:50 White-light moment with AT&T campaign and marketing blind spots

18:50 Age dysmorphia, beauty industry challenges, and why older audiences are complex

21:27 From Ageist to Super Age: growth, readership, and global impact

25:27 Health transformation and connecting mindset with the body

30:00 Teaching moments: embodied wisdom, confidence, and breaking limits

33:55 What Super Age does: informing, inspiring, and offering trusted tools

35:10 Longevity pillars: sleep, fitness, stress management, and community

37:31 Why grip strength and VO₂ max matter for longevity

41:42 Smart habits vs. fads: avoiding “dumb stuff” and focusing on basics

44:39 Managing stress, hormetic adaptation, and resilience

45:00 Why men chase longevity more than women

46:04 Thoughts on Brian Johnson and longevity biohacking

47:50 The future of health: AI-driven personalized medicine

51:28 Wearables: when they help vs. when they hurt

53:12 Passing wisdom to the next generation: embracing greatness and usefulness

56:15 Final reflections: passion, usefulness, and living as a contender

Learn more about MEA at ⁠https://www.meawisdom.com/

#Longevity #HealthyAging #RedefiningAging #SuperAge #Ageist #MidlifeReinvention #MindsetMatters #AgingWell #LifeAfterCrisis #HealthTransformation #Vitality #BreakingAgingStereotypes #AgingStrong #LongevityLifestyle #AgelessLiving

What happens when a bestselling writer and a former corporate executive dive deep into life’s second half?

In this powerful conversation, Anne Lamott and Neal Allen share raw, funny, and moving stories about midlife transformation, spiritual awakening, recovery, and how to finally silence that relentless inner critic. From faith and writing to intimacy, aging, and finding purpose, their wisdom will leave you inspired — and maybe even rethinking your own path.

👉 Don’t miss this chance to hear life-changing insights from two voices who know the journey inside out. Watch now and discover how midlife can become your most powerful chapter yet.

Timestamps:

00:00 From Corporate Life to Spiritual Coaching

06:08 Annie’s Christian Spirituality

08:19 Annie’s Childhood, Religion & Humor

12:46 Embracing Christianity in a Ghetto Church

14:40 Annie’s Left-Wing Christianity Views

17:23 Anne’s Washington Post Columns on Aging

21:04 Imposter Syndrome & Life After 50

24:50 The Value of Intimacy & Deeper Connection

28:51 Taming the Inner Critic Workshop

33:46 Wisdom Bumper Stickers

Learn more about MEA at ⁠https://www.meawisdom.com/

#AnneLamott #NealAllen #MidlifeChrysalis #SpiritualGrowth #LifeAfter50 #InnerCritic #WritingCommunity #RecoveryJourney #ChristianSpirituality #PersonalTransformation #MindfulnessPractice #AgingWisdom #SpiritualCoaching #SelfAwarenessJourney #FaithAndHealing

What if the most painful disruptions in life—illness, job loss, divorce, or even an empty nest, were actually the keys to growth?

Bestselling author Bruce Feiler shares how “life quakes” shake up our stories and push us to rewrite them. From his own battle with cancer and family upheaval to studying hundreds of life transitions, Bruce reveals why resilience is a skill, not a trait, and how rituals, creativity, and storytelling can turn crisis into renewal. Dive into his powerful seven tools for navigating transitions, learn why the myth of the midlife crisis is outdated, and how to finally become the hero of your own story.

✨ Tune in to discover how to transform life’s hardest moments into your greatest turning points.

Timestamps:

00:00 Intro

00:40 Introduction to Bruce Feiler

02:24 Background, early life & first book

07:09 Life quakes and losing control of your story

12:15 Knowing when a transition is complete

18:11 The three stages of transition

24:40 Seven tools for navigating transitions

30:31 Acceptance and rituals to mark change

35:18 The ritual renaissance & new book preview

41:28 Routine vs. ritual explained

45:09 Shedding habits & finding creativity

49:19 Updating your story & unveiling your new self

51:19 The debate: midlife vs. transitions at all ages

58:51 Wisdom bumper sticker

01:04:22 Closing reflections & gratitude

Learn more about MEA at ⁠https://www.meawisdom.com/

#BruceFeiler #LifeQuakes #MidlifeTransitions #ReinventYourself #LifeIsInTheTransitions, #PersonalGrowth #OvercomingCrisis #FindingMeaning #ResilienceInMidlife #RewriteYourStory #RitualsAndRenewal #MidlifeReinvention #SelfDiscoveryJourney #ThrivingThroughChange #BeTheHeroOfYourStory

What if the path to a meaningful life had nothing to do with fame or success and everything to do with service and soul?

In this captivating conversation, Rainn Wilson opens up about his transformation from Hollywood ego to spiritual seeker, sharing how faith, meditation, and humility helped him rediscover purpose beyond the spotlight. Together with Chip Conley, he explores why midlife can be a sacred turning point when the soul finally takes the lead.

👉 Watch now to learn how Rainn’s journey can help you reconnect with your own soul.

Timestamps:

00:00 Introduction

02:55 What Is a Soul?

05:52 Chip‘s Definition of Soul

08:18 Humans on a Spiritual Journey

09:32 Growing Up Baha’i

13:58 The 1960s Spiritual Revolution

17:31 Hollywood, Faith & the Dark Night of the Soul

21:01 Becoming Dwight Schrute

22:50 Famous in Midlife

29:01 The Ego and Hollywood

31:38 Letting the Soul Lead

34:08 Devotion & Daily Practice

40:03 The Soul Boom Workbook

42:24 How the Workbook Came to Be

44:41 Wisdom Bumper Sticker

49:24 Chip’s Reflections and Takeaways

Learn more about MEA at https://www.meawisdom.com/

#RainnWilson #SoulBoom #MidlifeChrysalis #ChipConley #SpiritualRevolution #Bahaifaith #SoulJourney #ModernSpirituality #EgoAndSoul #Mindfulness #PersonalGrowth #MentalHealthAwareness #ServiceAndPurpose #ConsciousLiving #SpiritualAwakening

What if the worst thing that ever happened to you became the very thing that set you free? 🌱 In this deeply moving episode, Dr. BJ Miller—physician, amputee, and palliative care visionary—shares how a near-fatal accident in college transformed his understanding of life, loss, and what it really means to live fully. From his journey through unimaginable pain to founding Mettle Health, BJ reveals how facing mortality can open the door to compassion, creativity, and peace.

If you’ve ever feared aging, grief, or change, this conversation will completely shift your perspective.

👉 Watch now and discover how to turn life’s hardest moments into your greatest teachers.

Timestamps:

00:00 Introduction

00:36 The Accident That Changed Everything

04:17 Processing Grief and Feeling “Seen”

09:27 Rebuilding Life in His 20s

14:46 From Art History to Medicine

16:24 Discovering Palliative Care

20:27 What Palliative Care Really Means

24:26 Spiritual Dimensions of Caregiving

27:16 What We Get Wrong About Death

29:42 Making All Healthcare Palliative

32:44 Founding Mettle Health

36:56 Advice for Caregivers

41:25 The Power of Grief

43:50 BJ’s Midlife Chrysalis

47:49 What People Regret Most Before Death

51:48 Dying as a Creative Act

55:25 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#BJMIller #MidlifeChrysalis #ChipConley #EndOfLifeCare #PalliativeCare #HospiceCare #GriefAndHealing #MidlifeWisdom #CaregivingJourney #FindingMeaning #LifeAndDeath #SpiritualGrowth #EmotionalResilience #MindfulLiving #AuthenticLife

Ever wondered what it really means to start over when the world thinks you’ve peaked? In this episode, Daniel Pink, bestselling author of Drive and The Power of Regret, reveals why midlife isn’t a crisis but a creative turning point. He talks about becoming a beginner again after 50, how regret can guide us toward what truly matters, and why lasting motivation comes from autonomy, mastery, and purpose, not paychecks.

👉 Watch now to learn how to reinvent yourself with clarity, courage, and curiosity.

Timestamps:

01:15 Early Career & Al Gore Years

04:12 Leaving Politics for Book Writing

07:05 The Book “Drive” & Science of Motivation

11:10 Leadership & Purpose Within Organizations

14:13 Living an Average Mid-40s Reality

17:08 The Midlife Chrysalis & Year-Long Sabbatical

22:04 Writing for The Washington Post

25:58 Becoming a Rookie at 50

30:00 The Science of Timing

32:03 Evaluating Autonomy, Mastery & Purpose

34:21 How He Wrote “The Power of Regret”

37:42 The Wisdom in Regret

39:24 Anticipated Regret in Action

42:34 On Retirement & Regeneration

46:16 The Idea of Gap Year at 50

49:38 Regenerative vs. Retirement Communities

51:49 Upsides & Downsides of Aging

55:20 Dan’s Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#DanielPink #ChipConley #ModernElderAcademy #MidlifeChrysalis #ThePowerOfRegret #DriveBook #AutonomyMasteryPurpose #MotivationScience #MidlifeReinvention #CareerReinvention #FindingPurpose #AgingWithPurpose #LifelongLearning #PersonalGrowth #MindsetShift

What happens when the person you love most slowly begins to disappear before your eyes? In this deeply emotional and inspiring conversation, Emma Heming Willis opens up about life with Bruce Willis following his diagnosis of frontotemporal dementia and how she turned heartbreak into purpose.

Joined by Helen Christoni, co-founder of Make Time Wellness, the two reveal why women’s brain health is so often ignored, what every caregiver needs to hear, and how to rediscover joy even in the hardest seasons of life.

👉 Watch now and learn how making time for yourself might just be the most powerful act of care there is.

Timestamps:

00:00 Intro

00:54 How Helen and Emma created Make Time Wellness

04:47 Hormones, estrogen loss, and dementia risk

06:03 Helen’s personal connection to dementia

08:04 Starting Make Time as Bruce’s symptoms appeared

08:51 How Emma met Bruce Willis and first signs of FTD

12:05 Understanding anosognosia and early dementia signs

15:29 The meaning of ambiguous loss for caregivers

18:45 Practical tools and exercises for caregivers

20:37 Redefining self-care and “making time”

21:20 How others can help caregivers in real ways

24:09 The caregiving crisis and policy change needed

28:43 Gender roles and men’s perspective on caregiving

31:00 Make Time Wellness mission and products

34:49 Bruce Willis’s current condition and progression

38:20 How their daughters are coping and family life

39:24 Emma’s and Helen’s advice for caregivers

40:57 Wisdom bumper sticker

44:57 Closing reflections and gratitude

Learn more about MEA at ⁠https://www.meawisdom.com/

#EmmaHemingWillis #HelenChristoni #MidlifeCaregiving #WomensBrainHealth #CaregiverSupport #FrontotemporalDementia #DementiaAwareness #MakeTimeWellness #MidlifeResilience #SelfCareReimagined #MidlifeWisdom #WomenSupportingWomen #CaregivingJourney #FindingJoyAgain #ModernElderAcademy

Ever wondered why some people get stronger, wiser, and more grounded with age?

In this powerful conversation, Laird Hamilton and Gabby Reece reveal why midlife is actually the most dynamic, resilient, and liberating season of life. They open up about growing up on islands, how they met, what keeps their partnership strong, and why presence, patience, and community matter more than ever. From breathwork and injury recovery to identity shifts, parenting, and purpose, they share the hard-earned wisdom that helps them stay grounded, strong, and deeply connected.

If you’re ready to see midlife as a chrysalis, not a crisis, this episode is for you. Watch now.

Timestamps:

00:00 Welcome

00:09 Childhood and Island Upbringing

05:06 How Gabby and Laird Met

09:24 Navigating Two Athletic Careers

14:26 Relationship with Your Aging Body

21:46 Breathwork and Training Philosophy

26:04 Books and Science Behind Breathwork

29:42 Midlife Crisis vs Midlife Chrysalis

37:59 What Gets Better With Age

41:51 Relationship With Risk and Mortality

45:36 Presence and Stillness

51:47 Wisdom Bumper Sticker

54:17 Closing Remarks

Learn more about MEA at ⁠https://www.meawisdom.com/

#LairdHamilton #GabbyReece #MidlifeWisdom #MidlifeChrysalis #HealthyAging #LongevityLifestyle #BreathworkTraining #MindBodyHealth #MidlifeTransformation #AgingWell #PeakPerformance #AthleteMindset #MidlifeGrowth #ModernElder #ChipConley

What if the secret to living longer isn’t in your genes… but in your mindset?

In this Wisdom Wednesday episode, Chip Conley reveals the surprising research showing how a simple shift in how we think about aging can add years—yes, actual years—to our lives. From Becca Levy’s longevity findings to Carol Dweck’s growth-mindset principles, Chip breaks down why curiosity, openness, and lifelong learning may be the real fountain of youth.

You’ll learn why “I’m too old to…” is one of the most dangerous beliefs we carry, how anticipated regret can propel us into action, and why midlife is actually one of the most powerful stages for reinvention.

If you’re ready to rethink what’s possible in your next chapter, this episode will change how you see aging forever.

Tune in now and start shaping the mindset that shapes your life.

Timestamps:

00:00 Canadian spelling banter

02:56 Shifting mindset on aging

05:59 Anticipated regret as motivation

07:50 Lifelong learning and curiosity

10:09 What gets better with age

11:21 You’re not “too old” for anything

14:18 Mindset as invisible life framework

15:40 Weekly mindset assignment and closing remarksWhich of the 12 Reasons Most or Least Resonates With You? https://chipconley.com/reasons-quiz/ Learn more about MEA at ⁠https://www.meawisdom.com/

#wisdomwednesday #midlifegrowth #agingmindset #growthmindset #proaging #lifelonglearning #longevitymindset #chipconley #meaprogram #mindsetshift #curiosityasapower #midlifetransitions #positiveaging #mindsetmatters #livebetterlonger

In the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really means in midlife. Chip shares the down-to-earth definition that guides his life and talks about the small, consistent practices that help him turn everyday experiences into something meaningful.

If you’re ready for conversations that spark growth, clarity, and courage…

▶️ Start with Episode 1 and begin your wisdom journey with us.

Timestamps:

00:00 Intro

00:22 Welcome to Wisdom Wednesdays

01:37 What is wisdom and why it matters

02:55 Life lessons as raw material

03:32 Mindfully sharing wisdom

05:28 Can wisdom be cultivated

08:06 The problem with AI wisdom

08:51 The chef metaphor

10:52 Wisdom during cancer treatment

12:51 Chip’s wisdom bumper sticker

14:12 How to start your wisdom practice

15:54 Final reflection

Learn more about MEA at ⁠https://www.meawisdom.com/

#WisdomWednesdays #ChipConley #MidlifeChrysalis #MidlifeWisdom #PersonalGrowthJourney #ModernElder #LifeLessons #MidlifeTransformation #EmotionalWellbeing #MindfulLiving #SelfAwareness #MidlifePurpose #JournalingPractice #InnerGrowth #ThrivingInMidlife

Midlife isn’t a crisis. It’s your greatest awakening.

In this inspiring episode, gerontologist and coach Barbara Waxman redefines aging through the lens of “Middleessence,” a stage of growth, purpose, and renewal. She reveals how to reclaim energy with her Energy Audit, why mindset matters more than genetics for longevity, and how lifestyle medicine helps you live undiminished at every age.

✨ Learn how to flourish, not fade, in your next chapter.

▶️ Watch now on YouTube or listen on Apple Podcasts.

Timestamps:

00:00 Meet gerontologist Barbara Waxman

00:28 How she became a gerontologist

02:56 What is “middle essence”

07:18 Adolescence vs. middle essence

13:37 Why happiness rises after 50

16:42 Debunking the midlife crisis myth

18:53 Redefining legacy and purpose

20:19 Barbara’s own midlife awakening

23:03 What is the Energy Audit

24:36 What lifestyle medicine really means

28:55 The 7 lifestyle levers for thriving

30:42 Mindset’s power in longevity

32:41 Mindset studies that changed lives

35:18 Well-being burnout explained

36:23 Self-care vs. self-indulgence

38:10 Solitude, introverts, and renewal

40:09 Unlocking longevity and the third span

45:46 Living undiminished and flourishing

46:49 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #BarbaraWaxman #MidlifeTransformation #MiddleEssence #LongevityMindset #HealthyAging #LifestyleMedicine #WomenOver40 #LifeTransitions #PersonalGrowth #MindsetShift #AgingWell #HumanFlourishing #EnergyAudit #PurposefulLiving

What if aging isn’t about decline, but about becoming more alive than ever?

The bestselling author and spiritual teacher Mark Nepo opens up about how surviving cancer reshaped his entire understanding of life, creativity, and purpose. He reveals the wisdom behind The Fifth Season, a time in life when the inner world begins to shine brighter than the outer one, and shares how to live and create with authenticity in midlife and beyond.

Mark’s reflections will move you, ground you, and remind you what it truly means to be present, wholehearted, and free.

🎧 Watch now and rediscover how beauty, suffering, and friendship all become part of life’s greatest art: your own becoming.

Timestamps:

00:00 Intro

00:23 The Fifth Season: Creativity in midlife

04:10 What the “Fifth Season” really means

05:28 How cancer changed Mark’s life

09:58 Facing death and finding purpose

12:00 What cancer taught him about life

13:18 Chip’s own cancer story

17:10 Realizing he was a poet

22:14 How Oprah discovered his book

24:47 Success, humility, and staying grounded

29:59 Mark’s Pirouettes poem

34:32 Creativity as a spiritual act

42:17 Aging and letting go of old identities

43:26 The tea ceremony and making lists

46:30 The poetry of friendship

51:14 Teaching at MEA

55:12 Free Fall poem

56:03 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MarkNepo #TheBookOfAwakening #TheFifthSeason #MidlifeChrysalis #ChipConley #MidlifeWisdom #SpiritualGrowth #MidlifeCreativity #PersonalTransformation #CancerSurvivor #MindfulnessJourney #AgingGracefully #PurposeInMidlife #SpiritualAwakening #PoetryOfLife #OprahBookClub #SoulWork #LivingFully #EmotionalHealing #AuthenticLiving

🔥 One night on air changed everything for Tamsen Fadal.

She was at the top of her game as a TV anchor when she suddenly started forgetting words and sweating through live broadcasts, without realizing she was entering menopause. That moment became the turning point that led her from journalism to advocacy. In this conversation, Tamsen shares how she turned confusion into purpose, launching The M Factor documentary and her book How to Menopause.

✨ Join us as we talk about redefining midlife, breaking the silence, and helping women everywhere navigate this powerful new chapter.

Timestamps:

00:43 Early Life and Losing Her Mother

02:44 Lessons from Her Mother and Family Values

04:06 Breaking Into TV News and Facing Stereotypes

07:11 Sexism and Ageism in the Media Industry

09:12 Defining Her On-Air Brand and Early Career Years

11:46 Moving to New York and Personal Life Changes

15:36 Advice to Her 40-Year-Old Self

17:01 Health Issues, Misdiagnosis, and Menopause

23:28 TikTok & Creating Awareness

25:29 Street Interviews, Documentary, and The Book

30:28 Understanding Perimenopause and Menopause

34:16 Hormone Therapy and Medical Education Gaps

36:35 Finding Certified Menopause Practitioners

38:48 How Men and Coworkers Can Be Supportive

41:25 Reframing Midlife and the “Bolden Years”

44:37 Purpose, Creativity, and Daily Motivation

46:28 Redefining Retirement and Lifelong Energy

48:22 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MenopauseAwareness, #Perimenopause, #MidlifeEmpowerment, #WomensHealth, #MenopauseSupport, #MenopauseEducation, #TamsenFadal, #ChipConley, #HowToMenopause, #TheMFactor, #MidlifeCrisisMyth, #BoldenYears, #HormoneTherapy, #MenopauseAdvocate, #MidlifeReinvention

What if awe was the secret ingredient to happiness? 🌿 In this episode, I sit down with UC Berkeley psychologist Dacher Keltner to explore how awe, compassion, and moral beauty can transform the way we live and age. We dive into the science of wonder — from the power of collective joy to how simple “awe walks” can boost your health, purpose, and connection.

✨ Join us as we uncover why we’re truly born to be good and how awe might just be the key to midlife renewal.

🎧 Tune in for the full conversation and get inspired to see life with fresh eyes.

Timestamps:

00:00 Chip welcomes Dacher and reflects on their friendship

00:18 Why people smile when they talk about Dacher

01:06 How early experiences shaped his empathy

03:32 Journey into psychology and emotion science

06:42 Discovering emotion in the human face

07:31 Writing Born to Be Good and redefining human nature

09:42 Science of compassion, gratitude, and kindness

13:15 How the study of awe began

14:17 What awe is and how it feels

18:24 Collecting awe stories from around the world

20:33 The eight wonders of awe

21:00 Collective effervescence and shared joy

23:44 Synchronizing with others through movement and emotion

25:01 How screens disrupt human connection

27:00 Moral beauty and the power of witnessing goodness

31:32 Moral beauty within community and everyday life

32:39 Awe and moral beauty in midlife

36:33 The Awe Walk study and its health benefits

39:47 Finding awe in daily moments

41:25 Inside Dacher’s “Cultivating Awe” workshop

43:51 Practicing awe through grief and gratitude

45:09 Wisdom bumper sticker: seeing hidden beauty in people

47:35 Love (agape) as the essence of awe

49:10 Closing reflections and gratitude

Learn more about MEA at ⁠https://www.meawisdom.com/

#awe #DacherKeltner #ChipConley #MidlifeChrysalis #CultivatingAwe #BornToBeGood #MoralBeauty #CollectiveEffervescence #ScienceOfAwe #HumanConnection #Mindfulness #EmotionalIntelligence #MidlifeWisdom #GratitudePractice #FindingPurpose

What happens when one of the NFL’s most celebrated athletes walks away from fame, fortune, and the life everyone else wanted for him? In this powerful episode, Ricky Williams, now known as Errick Miron, opens up about his transformation from Heisman Trophy winner to healer, teacher, and astrologer. He shares how depression, self-discovery, and spirituality reshaped his identity and helped him find peace beyond the game.

If you’ve ever wondered what it truly means to let go and start over, this conversation will change the way you think about success, purpose, and freedom.

🎧 Listen now and discover how Ricky Williams became Errick Miron and found his true self.

Timestamps:

00:42 Early Ambitions and Upbringing

02:19 Choosing the University of Texas

04:54 College Glory and the Heisman Dream

07:37 NFL Reality Check

10:00 Mental Health and Identity Crisis

15:00 Discovering New Passions

16:14 Leaving the NFL & Coming Back

19:47 Journey to Australia and Discovering Ayurveda

22:32 First Encounter with Astrology

24:26 Return to Football with New Purpose

26:31 Preparing for Life After Sports

29:02 Retirement & Going Back to Astrology

38:41 Evolutionary Astrology Explained

42:46 Meeting His Wife & Becoming Errick Miron

47:21 Redefining Masculinity

49:42 Upcoming Workshop: Evolving Identity

52:16 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#RickyWilliams #ErrickMiron #MidlifeChrysalis #EvolvingIdentity #NFLtoAstrology #MentalHealthJourney #SpiritualAwakening #HealingJourney #AthleteTransformation #AstrologyForGrowth #LifeAfterSports #SelfDiscovery #PersonalGrowth #MasculineHealing #MindfulnessInMidlife

What if everything you’ve believed about midlife is completely outdated?

In this powerful conversation, Marianne Williamson sheds light on the truth about aging, visibility, and what it truly means to enter the second half of life with purpose. She shares raw reflections on menopause, identity shifts, modern rites of passage, and why midlife is less a crisis and more a spiritual turning point. Marianne also speaks about wisdom, reinvention, societal expectations, and how embracing your “third chapter” can unlock a deeper, more courageous version of yourself.

If you’re ready to rethink aging and step into your next chapter with clarity and confidence, watch the full episode now.

Timestamps:

00:00 Midlife awakening as unmapped territory

01:16 Aging, visibility, and grief for past identities

04:30 Rites of passage and communal transitions

08:13 Policy, culture shift, and public support

11:49 Government support for wisdom schools

13:06 Reflections on running for president

18:34 Midlife crisis vs chrysalis

19:14 Phase transition of society

21:31 Pattern recognition, memory, and wisdom

24:40 Teaching wisdom to younger generations

27:45 Family patterns, shadows, and generational conditioning

34:43 “Our deepest fear” and women’s empowerment

38:59 Cellular memory of witch burning

41:38 Sisterhood, bravery, and supporting each other

43:56 Re-inspiring midlife and visibility as women age

47:00 Presence, faith, and receiving life’s lessons

49:16 Chapter three as a crescendo

50:52 Midlife as a call to the soul

52:04 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#midlifeawakening #midlifecrisis #midlifewomen #agingwell #spiritualgrowth #womenswisdom #reinvention #mariannewilliamson #midlifetransformation #menopausejourney #mindfulnesspractice #lifepurpose #selfreinvention #modernelder #innerwisdom

What if living to 100 is more realistic than you think?

Longevity expert Dan Buettner breaks down the real habits behind the world’s longest-living people, from food and movement to purpose, community, and stress relief. He explains why Americans age faster, what actually adds years to your life, and how simple daily choices can transform your future health.

A simple, science-backed path to your best chapter yet. Watch now.

Timestamps:

01:25 What society gets wrong about aging

04:05 Dan’s early life and big expeditions

06:33 Why anti-aging shortcuts don’t work

09:10 Proven habits for longevity

15:42 The alcohol debate and new research

18:56 Benefits of drinking moderately

21:29 Why 65 isn’t “old” anymore

25:02 What the US gets wrong about health

28:51 Processed food, inactivity, and social media

30:52 Blue Zones work in US cities

35:13 What’s happening in original Blue Zones

37:40 New insights for Dan’s next book

39:59 Dan’s divorce and midlife chrysalis

42:31 How Blue Zones became a concept

46:17 What Dan would regret not doing

48:45 Dan’s experience at MEA

51:07 Netflix series and frozen meals success

51:58 Wisdom bumper-sticker

55:19 The role of humility and aging

55:59 The need for a rite of passage at 50

56:19 Why midlife can be the best stage of life

Learn more about MEA at ⁠https://www.meawisdom.com/

#BlueZones #Longevity #DanBuettner #HealthyAging #LiveLonger #HealthSpan #MidlifeChrysalis #AgingWell #LongevitySecrets #LiveTo100 #HealthyLiving #PurposefulLiving #HolisticHealth #LifestyleMedicine #Wellbeing

What if midlife is actually the start of your happiest years?

In this episode, Chip Conley and Derek Gehl break down why life often gets better after 50, from rising emotional intelligence and deeper wisdom to feeling more like your true self. Chip explains why “growing whole” matters more than “staying young,” how Carl Jung’s insights can reshape your mindset, and why a pro-aging outlook can change your health, relationships, and purpose.

If you want a fresh, hopeful take on midlife, don’t miss this conversation. Watch now.

Tune in, and take the quiz! 👇 https://chipconley.com/reasons-quiz/"The Midlife Checkup Quiz"

Timestamps:

00:00 Welcome to Wisdom Wednesday

03:12 Beauty of Santa Fe winters

03:15 Introducing Chip’s book

04:32 Growing whole as we grow older

06:31 Integrating all parts of ourselves

07:46 Stories about aging from Chip’s parents

09:18 Why Chip founded MEA

11:20 Midlife Checkup Quiz

12:07 Time affluence and midlife

14:29 Creating a pro-aging friend group

16:34 Closing thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

Which of the 12 Reasons Most or Least Resonates With You?

https://chipconley.com/reasons-quiz/ 

#MidlifeWisdom #ProAging #AgingWell #MidlifeGrowth #UCurveOfHappiness #EmotionalIntelligence #LifeAfter50 #MidlifeTransformation #HealthyAging #ChipConley #MidlifeMindset #PersonalGrowthJourney #WisdomWednesday #IdentityGrowth #MEACommunity

What happens when Don Lemon gets truly unfiltered?

In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older.

Don also reflects on the state of media, the “prime” controversy, and how stepping away from traditional news helped him reclaim his voice and his joy. If you’re ready for truth, evolution, and a warm reminder that life after 50 can get better, tune in. Watch now.

Timestamps:

00:00 Chip’s episode opening

00:57 Don on aging and happiness

02:34 Don’s childhood and early years

03:38 Politics, Reagan, and identity

06:52 Dating while closeted

09:52 College years and social life

12:17 First gay bar experiences

16:20 Don’s coming-out story

19:47 Coming out publically in a book

21:41 Midlife chrysalis and confidence

25:10 What gets better with age

28:28 The “prime” controversy explained

34:07 State of media and independence

36:30 Politics, division, and future outlook

37:26 Don on never retiring

38:49 Possible regret 10 years from now

40:24 Don’s wisdom bumper sticker

43:543 Judy Garland and music icons

46:50 Chip’s reflections

Learn more about MEA at ⁠https://www.meawisdom.com/

Keywords:

#DonLemon #midlife #agingwell #lifeafter50 #midlifefreedom #midliferenaissance #comingoutstory #lgbtqstories #authenticitymatters #selfacceptance #personaltransformation #midlifewisdom #findingyourvoice #reinventyourlife #unfilteredconversation

Grief isn’t just an emotion, it’s energy that lives in the body until we face it.

I sit down with Meghan Jarvis, a trauma therapist and grief mentor who’s helped countless people find their way through loss. Meghan shares her own story of heartbreak, how grief and trauma intertwine, and the six simple practices she teaches to move that heavy energy through the body and back toward healing. We also talk about midlife transitions, why so many of us feel stuck, and how community can bring us back to life.

👉 Tune in for a real, hopeful conversation about what it truly means to grieve, heal, and grow.

Timestamps:

00:00 Childhood loss that led her to grief work

02:13 Uncovering long-buried trauma

06:02 What trauma teaches about safety and fear

09:29 Grief as energy moving through the body

11:07 How stored grief affects physical health

13:02 Losing her parents and lessons learned

17:29 Checking into treatment and finding purpose

19:32 The vagus nerve and how the body heals

22:19 Midlife transitions and hidden grief

24:18 Helping clients rewrite their stories

26:12 The six pillars of the Grief Mentor Method

31:11 Mindfulness, nourishment, and rituals for healing

39:13 Why midlife brings old losses back

42:21 Signs of unresolved grief

43:55 Finding meaning and joy after healing

47:43 MEA as a space for renewal

51:44 Meghan’s wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeHealing #GriefJourney #EmotionalHealing #MeghanJarvis #LifeTransitions #MidlifeGrowth #HealingAfterLoss #MindBodyConnection #GriefSupport #TraumaRecovery #FindingPurpose #PersonalGrowth #MidlifeAwakening #MentalHealthAwareness #ChipConley

What if everything you’ve believed about aging and retirement is wrong?

In this week’s Wisdom Wednesday, Chip and Derek dive into the surprising truth about aging. Why retirement often makes us less healthy, how community and purpose keep us alive longer, and why our “crystallized intelligence” actually gets stronger well into our 60s and 70s. They explore the real ingredients of a meaningful midlife, the magic of third-vault conversations, and the stories of people who’ve traded old scripts for more inspired lives.

If you’re ready to feel hopeful, energized, and a little more excited about the years ahead, watch the full episode.

Timestamps:

00:00 Intro

00:34 Welcome to Wisdom Wednesdays

01:43 The origins of age 65 retirement

02:59 How retirement affects lifespan

04:08 Fluid intelligence vs crystallized intelligence

06:01 What people need the most after 50

08:27 Chip’s own “mini retirement”

10:07 Rethinking the three-stage life

11:58 The litigator who became a baker

14:11 Keeping your options open

16:15 Changing habits by changing habitat

17:16 The concept of the third vault

20:12 Deeper conversations with aging

20:56 Episode wrap-up and closing remarks

Learn more about MEA at ⁠https://www.meawisdom.com/

#midlifechrysalis #agingwell #longevitymindset #midlifetransformation #purposeafter50 #crystallizedintelligence #rethinkingretirement #healthyaging #midlifewisdom #lifepurpose #aginggracefully #lifestages #livingto100 #midlifecommunity #wisdomwednesdays

Ever wonder if slowing down might actually wake you up? In this episode, I sit down with Susan Cain, the bestselling author of Quiet and Bittersweet, to talk about the hidden strengths of introverts, the surprising beauty in melancholy, and why midlife can be the most creative and peaceful chapter of your life. We dig into what it really means to live with depth, authenticity, and joy, without the noise.

✨ Hit play and join us for a quiet conversation that might just change how you see yourself.

Timestamps:

00:18 The Quiet Life Community

01:23 Susan’s early career as a corporate lawyer

02:18 Realizing law wasn’t her path

03:25 The success of Quiet and its life-changing impact

06:09 Defining introversion and extroversion

09:43 Chip’s story: from introvert to social alchemist

11:35 Why people grow more introverted with age

13:24 Reputational confusion and being open

17:56 What is “Worktrovert”

20:17 Deeper happiness through the bittersweetness

23:05 Daily practices to balance beauty and melancholy

25:44 The power of remembering mortality

27:45 Chip’s near-death experience and slowing down

30:31 Slowing life down in midlife and releasing ambition

33:01 Leaving law and embracing a quiet, creative life

38:31 How awareness of death deepens appreciation for life

40:53 What Susan’s working on now

43:07 Liz Gilbert’s TED Talk and creative pressure

45:50 Susan’s advice for aspiring writers

49:41 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#SusanCain #ChipConley #MidlifeChrysalis #QuietLife #Introversion #Bittersweet #SelfDiscovery #MidlifeTransformation #EmotionalIntelligence #PersonalGrowth #QuietPower #LifeTransitions #MindfulLiving #AuthenticLife #CreativityAndCalm

What happens when two New York City professionals lose their jobs, move to a tiny rural town, and accidentally build one of America’s most beloved skincare brands?

Brent and Josh of Beekman 1802 reveal how kindness, community, and old-fashioned wisdom became the backbone of their business and their midlife reinvention. They share how loving your neighbor can be a real strategy, why contentment matters more than achievement, the 51% rule that keeps their partnership strong, and how better aging starts with simple kindness to yourself and others, all delivered with warmth, wisdom, and humor.

👉 If you’re ready for a kinder, clearer way to think about midlife, just press play.

Timestamps:

00:00 Intro

00:59 Meet Brent & Josh of Beekman 1802

02:47 How Brent & Josh met

04:18 Brent’s upbringing & coming out journey

06:01 Becoming goat farmers & starting Beekman 1802

07:19 How the brand got its name

09:09 Turning a recession into a business opportunity

10:35 Growing from homemade soap to a global brand

12:54 The idea behind Goat Wisdom book

16:33 Their favorite principles

20:46 Community, kindness & homophobia

25:38 Brent’s family and true Christian acceptance

28:41 Being partners in love and business

29:56 The 51% Rule for decision-making

32:06 Radical transparency as kindness

34:37 Personal midlife philosophies

38:42 What they’d regret in 10 years

40:36 Redefining success as contentment

41:55 “Better aging,” social connection & kindness

45:16 Farm wisdom for life

48:56 Wisdom bumper stickers

52:12 Chip’s closing reflections

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeTransformation #GoatWisdom #Beekman1802 #ChipConley #MidlifeChrysalis #BetterAging #KindnessCulture #EntrepreneurJourney #LifeReinvention #ContentmentOverAchievement #LGBTQEntrepreneurs #ModernElders #AgingWisdom #MidlifeReinvention #SmallTownStories

What if midlife became your chance to ROAR, not retire?

In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how reinvention is not only possible, it’s essential.

He breaks down the ROAR framework for reimagining your future, explains why “life layering” is the antidote to midlife crisis, and dives into the emerging world of longevity science, age-positive culture, and purpose-driven living. If you’ve ever wondered what’s next, or what’s possible, this episode shows you how to build a richer, more meaningful second half of life.

Watch now and start reimagining what your future can be.

Timestamps:

00:00 Michael’s Santa Fe moment

01:31 Early life, father’s influence, love of words

05:27 A career in publishing

08:02 Midlife awakening at 39

10:50 Climbing Kilimanjaro and building an adventurous life

12:32 Returning to school at 67

15:56 The ROAR framework begins

20:00 Ageism, language shifts, modern role models

25:13 Life layering and building new identities

27:45 Preparing for post-career life

29:01 Reinvention stories and reimagineers

30:51 Relationships, editing your circle, and support systems

35:25 Growth mindset and lifelong curiosity

37:33 Longevity insights and the next book

39:18 Why longevity is having a cultural moment

44:01 Why the US is falling behind on lifespan

45:22 Rethinking work, age diversity, and longer careers

49:56 Longevity clinics and new health models

52:57 Longevity travel and residential communities

54:35 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeReinvention #Longevity #PurposeAfter50 #ReimaginingAging #LifeLayering #ROARMethod #SecondHalfOfLife #HealthyAging #MidlifeAwakening #RewireNotRetire #AgingWell #LiveLongerBetter #MidlifeTransformation #ModernAging #LifelongLearning

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.

In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.

Chip shares:

• The three stages of every transition and where most people get stuck

• What really happens inside the messy middle

• Why men and women experience midlife so differently

• How transitional intelligence (TQ) helps you move forward with clarity

If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need.

If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights.

Timestamps:

00:00 Film Festival & Holiday Mood

01:55 Crisis vs Chrysalis and the Hollywood Myth

05:15 The Three Stages of Transition

07:07 Emotions in the Messy Middle

09:33 Finding Your Through Line

11:21 Ritualizing Endings

13:16 How Men Experience Midlife

15:40 How Women Experience Midlife

15:53 Why Women Navigate Midlife Differently

19:27 Identity, Purpose, and Feeling Stuck

21:35 Chip’s Personal Midlife Story

22:42 Why Men Resist This Work

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #MidlifeTransition #MidlifeCrisis #MessyMiddle #PersonalGrowthJourney #LifeTransitions #ChipConley #TransitionalIntelligence #MidlifeWisdom #SelfDiscovery #MidlifeWomen #MidlifeMen #EmotionalWellbeing #LifeReinvention #GrowthMindset

Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you.

In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel reframes dating not as luck but as a learnable skill, especially in midlife.

Together, we explore:

- Why the people who make us happiest don’t always match our dating checklists

- How chemistry can fool us and what actually leads to lasting connection

- The quiet dating rules that keep smart people single

- Why love often shows up in unexpected packages

- How modern couples are redefining partnership, including living apart together

This is a hopeful, practical conversation about dating with wisdom, curiosity, and openness, not fear or frustration.

👉 Listen or watch now and discover why midlife may be your most meaningful, and romantic, chapter yet.

Timestamps:

00:46 Meet matchmaker Rachel Greenwald

03:36 From Harvard MBA to professional matchmaker

04:03 A midlife pivot that changed everything

07:29 The highs and lows of matchmaking

09:44 What is keeping people single

10:20 The most powerful question in dating

13:11 Chemistry vs compatibility & happiness

17:11 Why we repeat unfinished relationship patterns

19:46 Why dating checklists can backfire

22:39 Why men make up most matchmaking clients

25:08 Why parents hire matchmakers for young adults

28:03 Why midlife dating isn’t hopeless

35:57 The three must-haves that really matter

38:26 Living apart together and modern relationships

44:51 Inside the Santa Fe dating workshop

48:27 Wisdom bumper sticker

53:11 Final takeaways on love and dating in midlife

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeDating #DatingAfter40 #DatingAfter50 #MidlifeRelationships #FindingLoveLaterInLife #DatingAdvice #ModernDating #RelationshipAdvice #DatingWisdom #MidlifeWomen #MidlifeMen #Matchmaking #LoveAfterDivorce #DatingOver40 #MidlifeChrysalis

Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.

In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning.

In this conversation, you’ll discover:

• Why great mentorship is a two-way exchange, not top-down advice

• How modern elders learn alongside younger generations

• The difference between a librarian mentor and a confidant mentor

• Why respect and curiosity matter more than credentials

• How asking the right questions creates real growth at work and in lifeIf you’re navigating midlife, leading across generations, or rethinking how you share your wisdom, this episode is for you.

Watch now and join us for Wisdom Wednesday. 

Timestamps:

01:58 Why mentorship matters in midlife

04:16 Digital natives vs digital immigrants

05:11 The respect gap in mentorship

06:20 Defining wisdom and lived experience

07:10 Four stages of becoming a modern elder

08:22 Appreciative inquiry and powerful questions

10:30 Librarian mentor vs confidant mentor

12:20 Chip Conley and Herb Kelleher mentorship story

14:20 How confidant mentorship builds confidence

15:45 How to structure a healthy mentorship

16:53 Mentors vs coaches explained

18:35 The mentorship gap and retention impact

18:51 How to start mentoring at midlife

20:55 Mentorship and renewed purpose

21:51 Final reflections and closing 

Learn more about MEA at ⁠https://www.meawisdom.com/

We’re surrounded by information but many of us still feel unsure about how to live well.

This episode gently explores why midlife pulls us toward wisdom, not more answers. Chip Conley is joined by bestselling author Eric Weiner (The Geography of Bliss, Man Seeks God, The Socrates Express), a curious guide who’s spent years learning from philosophers, cultures, and lived experience. Together, they talk about what ancient wisdom can teach us about modern life—especially when certainty starts to fall away. 

In this conversation, you’ll hear:

• Why midlife naturally turns us into philosophers
• The difference between knowing more and living better
• How thinkers like Socrates, Thoreau, and Marcus Aurelius offer practical guidance
• Why wonder, humility, and generosity matter more than expertise
• Simple ideas that help us navigate change, relationships, and uncertainty

 This is a warm, thoughtful, and often playful conversation about slowing down, asking better questions, and learning how to live with more clarity and meaning.

Watch now and step into the wisdom midlife is inviting you to explore. 

Timestamps:

04:21 Welcome to Midlife Chrysalis

04:59 Writing with humility and vulnerability

07:02 Book titles and framing ideas

08:34 Geography of Bliss origin story

12:31 Favorite places and soul place

13:54 Ben Franklin and usefulness

18:31 Writing about God and belief

21:44 Geography of Genius and creativity

23:30 Introducing The Socrates Express

24:10 Knowledge vs wisdom

27:23 What philosophy really is

30:38 Wonder vs curiosity

34:40 Stoicism and modern relevance

37:33 Philosophers that resonated most

40:53 Thoreau and learning how to see

44:52 Why philosophy matters in midlife

49:20 Wisdom bumper stickers

52:26 Closing and Santa Fe workshop 

Learn more about MEA at ⁠https://www.meawisdom.com/

What happens when ambition slows down, and wisdom begins to lead? Chip Conley, founder of Modern Elder Academy and host of Midlife Chrysalis, sits down with California Governor Gavin Newsom for a rare, deeply personal conversation shaped by nearly 30 years of mentorship and friendship. This is not a political interview, it’s an honest exploration of midlife, identity, and becoming.Together, they reflect on:

• How Gavin’s upbringing and dyslexia shaped his leadership
• Why legalizing same-sex marriage became a defining moral moment
• What the “winter years” between mayor and governor revealed
• How fatherhood and midlife reshaped his relationship with power
• Why grace, humility, and resilience matter now more than ever

Warm, thoughtful, and deeply human, this episode explores what’s possible when we slow down and listen. If you’re navigating change or reinvention, watch now and step into the chrysalis.

Timestamps:

03:26 Welcome to Midlife Chrysalis

04:06 Long friendship and early mentorship

05:54 Childhood and family background

08:48 Gavin’s writing experience

16:03 Becoming mayor of San Francisco

17:38 Decision to legalize gay marriage

25:11 Impact of marriage equality

27:54 Political winter as lieutenant governor

29:24 Identity loss and slowing down33:21 Humility and leadership lessons

35:22 Grace humility after years of division

38:46 The lost art of civil disagreement41:49 Political vision and building bridges

44:10 Stoicism and wisdom traditions

47:44 Fatherhood and authenticity

49:27 Wisdom bumper stickerLearn more about MEA at ⁠https://www.meawisdom.com/

What happens when success stops working and midlife hits hard?

Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement.

Blake opens up about:

- How selling part of TOMS triggered an unexpected identity collapse

- Why midlife depression often follows success, not failure

- The treatments and inner work that helped him recover, including ketamine therapy and TMS

- The simple but life-changing realization that shifted everything: “I am enough”

- Why connection and community matter more than success or status

👉 Watch now to hear Blake Mycoskie’s most vulnerable and meaningful story yet.

Timestamps:

01:11 Blake’s early entrepreneur journey

02:49 Reality Central and first major failure

04:59 The business lesson that shaped TOMS

07:49 Creating the one for one model

08:43 Selling TOMS and losing identity

12:36 Depression behind the public image

16:23 Searching for relief outside himself

17:24 Medication fog and deep isolation

19:30 Why telling others saved his life

20:54 Moving beyond traditional medication

21:12 Ketamine and TMS

25:53 Discovering the core wound

28:49 India and lasting inner freedom

33:27 Launching the Enough initiative

35:58 I’m Enough ritual poem

37:57 How the nonprofit model works

38:47 The growing mental health crisis

43:13 Self compassion and flow state

46:28 How to support someone in depression

51:54 Living with fear of relapse

54:17 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#BlakeMycoskie #MidlifeCrisis #MentalHealthAwareness #EntrepreneurMentalHealth #SuccessAndDepression #TOMSFounder #MidlifeJourney #DepressionRecovery #FindingPurpose #SelfWorth #MentalHealthPodcast #MidlifeTransformation #HealingJourney #MenAndMentalHealth #IAmEnough

What if aging alone isn’t the only option?

As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude?

In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe to address loneliness, gray divorce, and the realities of solo aging.

In this episode, you’ll learn:

- Why more women are aging solo in midlife

- Why social connection matters more than health hacks

- How housing no longer fits modern midlife needs

- What Golden Girls–style living could look like in practice

This isn’t a finished solution — it’s a timely experiment that reimagines how we live and age.

👉 Watch now and decide if community belongs in your next chapter.

Timestamps:

02:40 Golden Girls homes concept

03:41 Gray divorce and solo agers

06:20 Loneliness and housing mismatch

08:05 Why Golden Girls homes now

10:10 The Santa Fe pilot homes

12:49 Workshops and community vision

15:29 What the research revealed

18:14 Matching roommates and house culture

21:10 Affordability and rental model

24:10 What about men

26:36 Long term vision and legacy

29:21 How to get involved

29:55 Final reflections

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #GoldenGirlsHomes #MidlifeTransition #SoloAgers #GrayDivorce #LonelinessEpidemic #IntentionalLiving #MidlifeCommunity #WomenOver50 #AgingWell #CommunityLiving #ModernElders #MidlifeWisdom #HousingInnovation #SocialConnection