From Famous Father to Finding Purpose: Scott Eastwood at Midlife
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 RelationshipLearn more about MEA at https://www.meawisdom.com/#ScottEastwood #MidlifeChrysalis #ChipConley #ClintEastwood #MasculinityToday #ActorLife #FilmIndustry #PersonalGrowth #LegacyAndIdentity #MidlifeReflection #LifeLessons #EmotionalMaturity #CreativeJourney #WellnessWisdom #FollowYourGut
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Why Krista Tippett Walked Away at the Peak of Her Career
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 Setup00:46 Introducing Lee and the Unique Cast of Guests01:52 What Makes a Great Interviewer?06:12 Interviewing John O’Donohue09:57 Thresholds and Transitions12:58 Krista’s Childhood and Upbringing in Oklahoma17:40 The Bible as Her First Text of Imagination20:00 Interviewing Richard Rohr and Men’s Spiritual Lives23:36 Krista’s Midlife Reflections27:06 Midlife Chrysalis and Personal Transformation30:53 Building a Life Around Love and Friendship35:36 What She’d Regret Not Doing38:09 What Brings Joy Now42:03 Defining Wisdom and Growing Wiser46:26 Staying Grounded Through Rituals and Attention51:43 Rethinking Retirement54:29 The Aging Brain and Synthesizing Wisdom57:46 Wisdom Bumper StickerLearn more about MEA at https://www.meawisdom.com/#MidlifeWisdom #OnBeing #KristaTippett #MidlifeTransformation #SpiritualGrowth #LifeAfter40 #InnerLife #FindingPurpose #EmotionalResilience #WomenOver40 #BecomingWise #SoulfulLiving #PersonalGrowthJourney #AgingWithGrace #DeepConversations
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What Burning Man Teaches Us About Aging, Identity & Legacy | Marian Goodell
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 Intro00:40 Chips Connection to Burning Man04:43 What Burning Man Really Is07:01 How Burning Man Became a Global Movement08:47 The Core Principles That Guide Everything11:13 Radical Self-Expression and Creating Without Expectation13:38 Why Burning Man Attracts People in Midlife Transition16:43 Loss, Legacy, and What We Leave Behind21:46 Lessons from Larry Harvey as a Modern Elder25:05 What She Learned as a Burning Man’s CEO33:00 What Is Fly Ranch and Why It Matters36:28 Fly Ranch Like Burning Man’s Feminine Side39:24 Three Tips for Burning Man First-Timers42:14 Burning the Man and Temple Rituals47:22 The Healing Power of Ritual50:08 Why MEA Resonates with Burners53:40 Wisdom Bumper StickerLearn more about MEA at https://www.meawisdom.com/#BurningMan #MidlifeCrisis #MidlifeTransformation #MarianGoodell #BurningMan2025 #PersonalGrowth #ReinventionAfter40 #MidlifeAwakening #LifeAfter50 #SpiritualJourney #BurningManExperience #RadicalSelfExpression #MidlifeChrysalis #ChipConley #PurposeInMidlife
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Psychedelics, Purpose & the Next Chapter of John Mackey’s Life
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 Intro00:27 Meet John Mackey01:27 Psychedelics, Ego Death, and Food as Purpose07:44 Love, Breakups, and Big Business Shifts08:37 Austin in the '70s and Building Whole Foods10:40 Advice to His Younger Self12:34 From Atheism to Spiritual Adventure14:36 What Is Conscious Capitalism?17:15 How Whole Foods Revolutionized Grocery Stores19:28 Learning to Communicate with Kindness21:46 Selling Whole Foods to Amazon28:17 Why He Finally Left Whole Foods29:25 Healing Journey Through Plant Medicine31:28 What Is Love Life?37:56 Psychodelics as Therapeutic Method40:21 Challenges and Financial Realities43:21 Longevity Myths and What Actually Works47:49 Redefining Retirement with Purpose49:54 What He’d Regret Not Doing52:09 Wisdom Bumper Sticker55:33 Final ReflectionsLearn more about MEA at https://www.meawisdom.com/#JohnMackey #WholeFoods #ConsciousCapitalism #MidlifeTransformation #LongevityTips #PlantMedicine #PsychedelicHealing #PurposeDrivenLife #HolisticHealth #LoveLifeWellness #SpiritualGrowth #EntrepreneurMindset #ChipConley #FoundersJourney #ReinventYourself
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Rich Roll on Reinventing Yourself After Rock Bottom
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 Recovery03:02 Losing Identity and Facing Stillness05:47 Interviewing Master Interviewers07:17 Life Begins at 40 & Rejecting the Race11:06 How to Know You’re on the Right Track13:42 Performance vs. Presence15:25 Addiction, Achievement, and the Roots of Disconnection19:49 The Midlife Chrysalis at Age 3924:29 The Support of His Wife Julie26:04 Lessons from Rich’s Midlife Chrysalis32:14 From Blog to Writing a Book38:10 Launching the Podcast & Relocating to Hawaii42:27 Gaining Momentum43:50 Financial Struggles and Family Impact48:14 What Makes Rich Roll’s Podcast Different51:58 The Importance of Genuine Curiosity54:25 The Power of Vulnerability in Conversation56:31 Rethinking Success and Slowing Down01:01:46 Legacy, Family, and Showing UpLearn more about MEA at https://www.meawisdom.com/#MidlifeTransformation #RichRoll #SpineSurgeryRecovery #SobrietyJourney #PurposeInMidlife #EnduranceAthlete #AddictionRecovery #MidlifeReinvention #PersonalGrowth #PodcastLife #EmotionalResilience #LifeAfter40 #LegacyWork #AuthenticLiving #ModernElder
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.
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