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

Welcome to the very first episode of The Midlife Chrysalis!

Chip Conley kicks off this amazing podcast by redefining midlife. It’s not as a crisis, but a powerful chrysalis for transformation.

He shares his own wild journey and reveals why your 40s, 50s, and beyond can be the most meaningful years of your life. Plus, get a sneak peek at upcoming guests like Maria Shriver, Brian Chesky, Gavin Newsom, and more.

If you're ready to reinvent yourself and thrive in midlife, this is your new go-to podcast.

Timestamps:

00:00 Welcome to The Midlife Chrysalis

00:40 My Journey from Crisis to Chrysalis

01:24 Midlife as Time of Major Transition

02:15 Why This Podcast Matters

02:24 Upcoming Guests

03:08 An Invitation to Join the Journey

Learn more about MEA at ⁠MEAWisdom.com

#MidlifeTransformation #ReinventYourLife #ModernElder #MidlifeJourney #AgingWithPurpose #MidlifeMotivation #LifeAfter40 #LifeAfter50 #SecondActSuccess #MidlifeReinvention #PurposefulLiving #LongevityMindset #ChipConley #UCurveOfHappiness #MidlifeWisdom