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

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

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 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