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 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 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 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 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