Education

The Midlife Chrysalis

The Midlife Chrysalis is a one-hour podcast hosted by Chip Conley, bestselling author of Learning to Love Midlife and founder of MEA (Modern Elder Academy). Chip and his high-profile guests – including Maria Shriver, Hoda Kotb, Elizabeth Gilbert, Michael Franti, and more – dive into raw, vulnerable conversations about the profound transitions they’ve experienced in midlife.

Listeners get a rare look at how even the most successful individuals have to navigate life’s pivotal changes – and gain practical wisdom they can apply in their own lives for a more fulfilling and purposeful next chapter.

Latest Episodes:

Arthur Brooks on How to Break Free from the Striver’s Curse in Midlife Oct 08, 2025

Show notes

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/

From Near Death to Super Age: David Stewart’s Bold Reboot Oct 01, 2025

Show notes

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

Midlife Awakening & Spiritual Growth with Anne Lamott & Neal Allen Sep 24, 2025

Show notes

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

How to Rewrite Your Story After a Life Quake with Bruce Feiler Sep 17, 2025

Show notes

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

Elizabeth Gilbert’s Untold Story of Love and Addiction Sep 10, 2025

Show notes

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

From Punk Rock Pastor to Spiritual Outlaw: Rob Bell’s Midlife Reinvention Sep 03, 2025

Show notes

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 Intergenerational Living Creates Purpose & Joy | Marc Freedman Aug 27, 2025

Show notes

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

Aging Boldly and Living on Your Own Terms with Karen Walrond Aug 20, 2025

Show notes

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

Martha Beck on Psychic Gifts, Polyamory, and Finding Purpose Aug 13, 2025

Show notes

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

How Sara Blakely Built Spanx and Found Her Next Big Purpose Aug 06, 2025

Show notes

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

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