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

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

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 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

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

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