Ever wonder if slowing down might actually wake you up? In this episode, I sit down with Susan Cain, the bestselling author of Quiet and Bittersweet, to talk about the hidden strengths of introverts, the surprising beauty in melancholy, and why midlife can be the most creative and peaceful chapter of your life. We dig into what it really means to live with depth, authenticity, and joy, without the noise.
✨ Hit play and join us for a quiet conversation that might just change how you see yourself.
Timestamps:
00:18 The Quiet Life Community
01:23 Susan’s early career as a corporate lawyer
02:18 Realizing law wasn’t her path
03:25 The success of Quiet and its life-changing impact
06:09 Defining introversion and extroversion
09:43 Chip’s story: from introvert to social alchemist
11:35 Why people grow more introverted with age
13:24 Reputational confusion and being open
17:56 What is “Worktrovert”
20:17 Deeper happiness through the bittersweetness
23:05 Daily practices to balance beauty and melancholy
25:44 The power of remembering mortality
27:45 Chip’s near-death experience and slowing down
30:31 Slowing life down in midlife and releasing ambition
33:01 Leaving law and embracing a quiet, creative life
38:31 How awareness of death deepens appreciation for life
40:53 What Susan’s working on now
43:07 Liz Gilbert’s TED Talk and creative pressure
45:50 Susan’s advice for aspiring writers
49:41 Wisdom bumper sticker
Learn more about MEA at https://www.meawisdom.com/
#SusanCain #ChipConley #MidlifeChrysalis #QuietLife #Introversion #Bittersweet #SelfDiscovery #MidlifeTransformation #EmotionalIntelligence #PersonalGrowth #QuietPower #LifeTransitions #MindfulLiving #AuthenticLife #CreativityAndCalm
What happens when two New York City professionals lose their jobs, move to a tiny rural town, and accidentally build one of America’s most beloved skincare brands?
Brent and Josh of Beekman 1802 reveal how kindness, community, and old-fashioned wisdom became the backbone of their business and their midlife reinvention. They share how loving your neighbor can be a real strategy, why contentment matters more than achievement, the 51% rule that keeps their partnership strong, and how better aging starts with simple kindness to yourself and others, all delivered with warmth, wisdom, and humor.
👉 If you’re ready for a kinder, clearer way to think about midlife, just press play.
Timestamps:
00:00 Intro
00:59 Meet Brent & Josh of Beekman 1802
02:47 How Brent & Josh met
04:18 Brent’s upbringing & coming out journey
06:01 Becoming goat farmers & starting Beekman 1802
07:19 How the brand got its name
09:09 Turning a recession into a business opportunity
10:35 Growing from homemade soap to a global brand
12:54 The idea behind Goat Wisdom book
16:33 Their favorite principles
20:46 Community, kindness & homophobia
25:38 Brent’s family and true Christian acceptance
28:41 Being partners in love and business
29:56 The 51% Rule for decision-making
32:06 Radical transparency as kindness
34:37 Personal midlife philosophies
38:42 What they’d regret in 10 years
40:36 Redefining success as contentment
41:55 “Better aging,” social connection & kindness
45:16 Farm wisdom for life
48:56 Wisdom bumper stickers
52:12 Chip’s closing reflections
Learn more about MEA at https://www.meawisdom.com/
#MidlifeTransformation #GoatWisdom #Beekman1802 #ChipConley #MidlifeChrysalis #BetterAging #KindnessCulture #EntrepreneurJourney #LifeReinvention #ContentmentOverAchievement #LGBTQEntrepreneurs #ModernElders #AgingWisdom #MidlifeReinvention #SmallTownStories
In the very first episode of Wisdom Wednesdays, Chip Conley and Derek Gehl sit down for a thoughtful, honest conversation about what wisdom really means in midlife. Chip shares the down-to-earth definition that guides his life and talks about the small, consistent practices that help him turn everyday experiences into something meaningful.
If you’re ready for conversations that spark growth, clarity, and courage…
▶️ Start with Episode 1 and begin your wisdom journey with us.
Timestamps:
00:00 Intro
00:22 Welcome to Wisdom Wednesdays
01:37 What is wisdom and why it matters
02:55 Life lessons as raw material
03:32 Mindfully sharing wisdom
05:28 Can wisdom be cultivated
08:06 The problem with AI wisdom
08:51 The chef metaphor
10:52 Wisdom during cancer treatment
12:51 Chip’s wisdom bumper sticker
14:12 How to start your wisdom practice
15:54 Final reflection
Learn more about MEA at https://www.meawisdom.com/
#WisdomWednesdays #ChipConley #MidlifeChrysalis #MidlifeWisdom #PersonalGrowthJourney #ModernElder #LifeLessons #MidlifeTransformation #EmotionalWellbeing #MindfulLiving #SelfAwareness #MidlifePurpose #JournalingPractice #InnerGrowth #ThrivingInMidlife
Midlife isn’t a crisis. It’s your greatest awakening.
In this inspiring episode, gerontologist and coach Barbara Waxman redefines aging through the lens of “Middleessence,” a stage of growth, purpose, and renewal. She reveals how to reclaim energy with her Energy Audit, why mindset matters more than genetics for longevity, and how lifestyle medicine helps you live undiminished at every age.
✨ Learn how to flourish, not fade, in your next chapter.
▶️ Watch now on YouTube or listen on Apple Podcasts.
Timestamps:
00:00 Meet gerontologist Barbara Waxman
00:28 How she became a gerontologist
02:56 What is “middle essence”
07:18 Adolescence vs. middle essence
13:37 Why happiness rises after 50
16:42 Debunking the midlife crisis myth
18:53 Redefining legacy and purpose
20:19 Barbara’s own midlife awakening
23:03 What is the Energy Audit
24:36 What lifestyle medicine really means
28:55 The 7 lifestyle levers for thriving
30:42 Mindset’s power in longevity
32:41 Mindset studies that changed lives
35:18 Well-being burnout explained
36:23 Self-care vs. self-indulgence
38:10 Solitude, introverts, and renewal
40:09 Unlocking longevity and the third span
45:46 Living undiminished and flourishing
46:49 Wisdom bumper sticker
Learn more about MEA at https://www.meawisdom.com/
#MidlifeChrysalis #BarbaraWaxman #MidlifeTransformation #MiddleEssence #LongevityMindset #HealthyAging #LifestyleMedicine #WomenOver40 #LifeTransitions #PersonalGrowth #MindsetShift #AgingWell #HumanFlourishing #EnergyAudit #PurposefulLiving
What if aging isn’t about decline, but about becoming more alive than ever?
The bestselling author and spiritual teacher Mark Nepo opens up about how surviving cancer reshaped his entire understanding of life, creativity, and purpose. He reveals the wisdom behind The Fifth Season, a time in life when the inner world begins to shine brighter than the outer one, and shares how to live and create with authenticity in midlife and beyond.
Mark’s reflections will move you, ground you, and remind you what it truly means to be present, wholehearted, and free.
🎧 Watch now and rediscover how beauty, suffering, and friendship all become part of life’s greatest art: your own becoming.
Timestamps:
00:00 Intro
00:23 The Fifth Season: Creativity in midlife
04:10 What the “Fifth Season” really means
05:28 How cancer changed Mark’s life
09:58 Facing death and finding purpose
12:00 What cancer taught him about life
13:18 Chip’s own cancer story
17:10 Realizing he was a poet
22:14 How Oprah discovered his book
24:47 Success, humility, and staying grounded
29:59 Mark’s Pirouettes poem
34:32 Creativity as a spiritual act
42:17 Aging and letting go of old identities
43:26 The tea ceremony and making lists
46:30 The poetry of friendship
51:14 Teaching at MEA
55:12 Free Fall poem
56:03 Wisdom bumper sticker
Learn more about MEA at https://www.meawisdom.com/
#MarkNepo #TheBookOfAwakening #TheFifthSeason #MidlifeChrysalis #ChipConley #MidlifeWisdom #SpiritualGrowth #MidlifeCreativity #PersonalTransformation #CancerSurvivor #MindfulnessJourney #AgingGracefully #PurposeInMidlife #SpiritualAwakening #PoetryOfLife #OprahBookClub #SoulWork #LivingFully #EmotionalHealing #AuthenticLiving
🔥 One night on air changed everything for Tamsen Fadal.
She was at the top of her game as a TV anchor when she suddenly started forgetting words and sweating through live broadcasts, without realizing she was entering menopause. That moment became the turning point that led her from journalism to advocacy. In this conversation, Tamsen shares how she turned confusion into purpose, launching The M Factor documentary and her book How to Menopause.
✨ Join us as we talk about redefining midlife, breaking the silence, and helping women everywhere navigate this powerful new chapter.
Timestamps:
00:43 Early Life and Losing Her Mother
02:44 Lessons from Her Mother and Family Values
04:06 Breaking Into TV News and Facing Stereotypes
07:11 Sexism and Ageism in the Media Industry
09:12 Defining Her On-Air Brand and Early Career Years
11:46 Moving to New York and Personal Life Changes
15:36 Advice to Her 40-Year-Old Self
17:01 Health Issues, Misdiagnosis, and Menopause
23:28 TikTok & Creating Awareness
25:29 Street Interviews, Documentary, and The Book
30:28 Understanding Perimenopause and Menopause
34:16 Hormone Therapy and Medical Education Gaps
36:35 Finding Certified Menopause Practitioners
38:48 How Men and Coworkers Can Be Supportive
41:25 Reframing Midlife and the “Bolden Years”
44:37 Purpose, Creativity, and Daily Motivation
46:28 Redefining Retirement and Lifelong Energy
48:22 Wisdom Bumper Sticker
Learn more about MEA at https://www.meawisdom.com/
#MenopauseAwareness, #Perimenopause, #MidlifeEmpowerment, #WomensHealth, #MenopauseSupport, #MenopauseEducation, #TamsenFadal, #ChipConley, #HowToMenopause, #TheMFactor, #MidlifeCrisisMyth, #BoldenYears, #HormoneTherapy, #MenopauseAdvocate, #MidlifeReinvention
What if awe was the secret ingredient to happiness? 🌿 In this episode, I sit down with UC Berkeley psychologist Dacher Keltner to explore how awe, compassion, and moral beauty can transform the way we live and age. We dive into the science of wonder — from the power of collective joy to how simple “awe walks” can boost your health, purpose, and connection.
✨ Join us as we uncover why we’re truly born to be good and how awe might just be the key to midlife renewal.
🎧 Tune in for the full conversation and get inspired to see life with fresh eyes.
Timestamps:
00:00 Chip welcomes Dacher and reflects on their friendship
00:18 Why people smile when they talk about Dacher
01:06 How early experiences shaped his empathy
03:32 Journey into psychology and emotion science
06:42 Discovering emotion in the human face
07:31 Writing Born to Be Good and redefining human nature
09:42 Science of compassion, gratitude, and kindness
13:15 How the study of awe began
14:17 What awe is and how it feels
18:24 Collecting awe stories from around the world
20:33 The eight wonders of awe
21:00 Collective effervescence and shared joy
23:44 Synchronizing with others through movement and emotion
25:01 How screens disrupt human connection
27:00 Moral beauty and the power of witnessing goodness
31:32 Moral beauty within community and everyday life
32:39 Awe and moral beauty in midlife
36:33 The Awe Walk study and its health benefits
39:47 Finding awe in daily moments
41:25 Inside Dacher’s “Cultivating Awe” workshop
43:51 Practicing awe through grief and gratitude
45:09 Wisdom bumper sticker: seeing hidden beauty in people
47:35 Love (agape) as the essence of awe
49:10 Closing reflections and gratitude
Learn more about MEA at https://www.meawisdom.com/
#awe #DacherKeltner #ChipConley #MidlifeChrysalis #CultivatingAwe #BornToBeGood #MoralBeauty #CollectiveEffervescence #ScienceOfAwe #HumanConnection #Mindfulness #EmotionalIntelligence #MidlifeWisdom #GratitudePractice #FindingPurpose
What happens when one of the NFL’s most celebrated athletes walks away from fame, fortune, and the life everyone else wanted for him? In this powerful episode, Ricky Williams, now known as Errick Miron, opens up about his transformation from Heisman Trophy winner to healer, teacher, and astrologer. He shares how depression, self-discovery, and spirituality reshaped his identity and helped him find peace beyond the game.
If you’ve ever wondered what it truly means to let go and start over, this conversation will change the way you think about success, purpose, and freedom.
🎧 Listen now and discover how Ricky Williams became Errick Miron and found his true self.
Timestamps:
00:42 Early Ambitions and Upbringing
02:19 Choosing the University of Texas
04:54 College Glory and the Heisman Dream
07:37 NFL Reality Check
10:00 Mental Health and Identity Crisis
15:00 Discovering New Passions
16:14 Leaving the NFL & Coming Back
19:47 Journey to Australia and Discovering Ayurveda
22:32 First Encounter with Astrology
24:26 Return to Football with New Purpose
26:31 Preparing for Life After Sports
29:02 Retirement & Going Back to Astrology
38:41 Evolutionary Astrology Explained
42:46 Meeting His Wife & Becoming Errick Miron
47:21 Redefining Masculinity
49:42 Upcoming Workshop: Evolving Identity
52:16 Wisdom Bumper Sticker
Learn more about MEA at https://www.meawisdom.com/
#RickyWilliams #ErrickMiron #MidlifeChrysalis #EvolvingIdentity #NFLtoAstrology #MentalHealthJourney #SpiritualAwakening #HealingJourney #AthleteTransformation #AstrologyForGrowth #LifeAfterSports #SelfDiscovery #PersonalGrowth #MasculineHealing #MindfulnessInMidlife
What if the path to a meaningful life had nothing to do with fame or success and everything to do with service and soul?
In this captivating conversation, Rainn Wilson opens up about his transformation from Hollywood ego to spiritual seeker, sharing how faith, meditation, and humility helped him rediscover purpose beyond the spotlight. Together with Chip Conley, he explores why midlife can be a sacred turning point when the soul finally takes the lead.
👉 Watch now to learn how Rainn’s journey can help you reconnect with your own soul.
Timestamps:
00:00 Introduction
02:55 What Is a Soul?
05:52 Chip‘s Definition of Soul
08:18 Humans on a Spiritual Journey
09:32 Growing Up Baha’i
13:58 The 1960s Spiritual Revolution
17:31 Hollywood, Faith & the Dark Night of the Soul
21:01 Becoming Dwight Schrute
22:50 Famous in Midlife
29:01 The Ego and Hollywood
31:38 Letting the Soul Lead
34:08 Devotion & Daily Practice
40:03 The Soul Boom Workbook
42:24 How the Workbook Came to Be
44:41 Wisdom Bumper Sticker
49:24 Chip’s Reflections and Takeaways
Learn more about MEA at https://www.meawisdom.com/
#RainnWilson #SoulBoom #MidlifeChrysalis #ChipConley #SpiritualRevolution #Bahaifaith #SoulJourney #ModernSpirituality #EgoAndSoul #Mindfulness #PersonalGrowth #MentalHealthAwareness #ServiceAndPurpose #ConsciousLiving #SpiritualAwakening
What if the worst thing that ever happened to you became the very thing that set you free? 🌱 In this deeply moving episode, Dr. BJ Miller—physician, amputee, and palliative care visionary—shares how a near-fatal accident in college transformed his understanding of life, loss, and what it really means to live fully. From his journey through unimaginable pain to founding Mettle Health, BJ reveals how facing mortality can open the door to compassion, creativity, and peace.
If you’ve ever feared aging, grief, or change, this conversation will completely shift your perspective.
👉 Watch now and discover how to turn life’s hardest moments into your greatest teachers.
Timestamps:
00:00 Introduction
00:36 The Accident That Changed Everything
04:17 Processing Grief and Feeling “Seen”
09:27 Rebuilding Life in His 20s
14:46 From Art History to Medicine
16:24 Discovering Palliative Care
20:27 What Palliative Care Really Means
24:26 Spiritual Dimensions of Caregiving
27:16 What We Get Wrong About Death
29:42 Making All Healthcare Palliative
32:44 Founding Mettle Health
36:56 Advice for Caregivers
41:25 The Power of Grief
43:50 BJ’s Midlife Chrysalis
47:49 What People Regret Most Before Death
51:48 Dying as a Creative Act
55:25 Wisdom Bumper Sticker
Learn more about MEA at https://www.meawisdom.com/
#BJMIller #MidlifeChrysalis #ChipConley #EndOfLifeCare #PalliativeCare #HospiceCare #GriefAndHealing #MidlifeWisdom #CaregivingJourney #FindingMeaning #LifeAndDeath #SpiritualGrowth #EmotionalResilience #MindfulLiving #AuthenticLife
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