Why do so many relationships lose intimacy over time, even when love is still there?

In this episode of Midlife Chrysalis, Chip Conley talks with renowned couples therapist Terry Real, creator of Relational Life Therapy and bestselling author of Fierce Intimacy and The New Rules of Marriage. For decades, Terry has helped couples understand why connection fades—and how to rebuild it.

In this conversation, he explains:

• Why love requires skills most people were never taught
• How childhood patterns quietly shape adult relationships
• Why traditional masculinity often blocks emotional intimacy
• How couples can reignite connection in midlife

Terry argues that relationships don’t fail because people stop caring, they fail because no one teaches us how to do intimacy well.

Watch the episode to learn the relationship skills that can change everything.

Timestamps:

01:30 Terry Real joins from Anguilla

03:01 What is Relational Life Therapy (RLT)

03:54 Why RLT takes sides in couples therapy

06:18 The core principles of RLT

08:14 Trauma triggers and childhood patterns in relationships

11:59 What holds men back in relationships

15:04 Redefining masculinity for intimacy

16:25 Patriarchy and the modern relationship crisis

18:23 Relational joy vs gratification culture

22:44 Reigniting intimacy as empty nesters

27:03 Why couples must confront resentment

29:46 Independence vs connection in long-term relationships

33:24 Are you really happy in your relationship

36:53 Why relationships require practice and skill

40:08 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#midliferelationships #relationshipadvice #intimacy #modernrelationships #couplestherapy #loveskills #relationshipskills #midlifechrysalis #emotionalintimacy #terryreal #relationshipgrowth #relationshipproblems #communicationinrelationships #longtermrelationships #midlifelove

The moment that breaks your life can also be the moment that transforms it.

In this episode of Midlife Chrysalis, Chip Conley sits down with comedian and writer Pete Holmes for a deep and surprisingly funny conversation about heartbreak, spirituality, and the search for meaning. Pete shares how a painful divorce in his twenties pushed him to fully commit to comedy and set him on a journey into consciousness, psychedelics, fatherhood, and what it really means to live a good life.

In this episode, Pete reveals:

• How his divorce became the turning point that changed his life and career
• Why humor may be one of the most powerful tools for healing
• What psychedelics taught him about consciousness and awareness
• Why midlife can actually be the most meaningful chapter of life
• The life-changing idea: don’t believe everything you think

Warm, honest, and thought-provoking, this conversation explores how laughter and self-awareness can transform even life’s hardest moments.

👉 Watch the full episode to hear Pete Holmes’ story and discover why humor might be the secret to a better life.

Timestamps:

03:46 Is Pete Christian Comedian?

06:25 Was Jesus Funny?

09:04 Humor Humility and Getting Older

10:44 Can You Train Your Sense of Humor?

13:41 Why Midlife Is Actually Better

15:36 Fatherhood and Life in His 40s

19:52 Turning 47 and the Happiness Curve

20:59 Divorce at 28 and the Turning Point

26:17 Why Comedy Exploded After 9/11

30:42 Humor as Healing for Pain

31:54 Comedy Is Saying What Everyone Thinks

35:46 Aging What Gets Worse and What Gets Better

39:50 Psychedelics and Spiritual Awakening

46:39 Bringing Spirituality Into Comedy

49:48 Pete Holmes’ Best Life Advice

54:33 Relationship Advice That Actually Works

56:19 Final Thoughts and Richard Rohr

Learn more about MEA at ⁠https://www.meawisdom.com/

#PeteHolmes #MidlifeChrysalis #MidlifeWisdom #ComedyPodcast #PeteHolmesInterview #StandUpComedy #SpiritualityAndComedy #MidlifeGrowth #PersonalGrowthPodcast #PsychedelicInsights #RichardRohr #LifeLessonsPodcast #ConsciousComedy #SpiritualAwakening #SelfDiscovery

What if the most powerful move you could make at midlife… is to pause?

In this episode of Wisdom Wednesday, Derek sits down with Chip Conley to explore the rise of the midlife sabbatical and why more people over 50 are choosing a reset instead of racing toward retirement.

Chip challenges the old “learn, earn, retire” model and introduces a new idea: the midlife pit stop — a courageous break to refuel before the next chapter.

In this conversation, you’ll learn:

• Why a sabbatical isn’t a vacation. It’s renewal
• How stepping away can strengthen your career and relationships
• What Chip discovered during his own two-year break
• How to design a meaningful month off, even if a year feels impossible

Midlife isn’t about slowing down. It’s about getting intentional.

If this resonates, share it with someone who might need a reset and subscribe for more Wisdom Wednesday insights.

Timestamps:

00:05 Spring Travel Chat & Baja Living

05:34 The Rise of the Midlife Gap Year

11:20 The Midlife Atrium Concept

13:15 Why Employers Should Support Sabbaticals

17:14 Starting Small with a Gap Weekend

18:07 Chip’s Two-Year Sabbatical Experience

23:13 Ego, Curiosity, and Deepened Friendships

24:31 How to Design a One-Month Sabbatical

26:58 Saving for a Midlife Pit Stop

29:19 Escaping One-Dimensional Living

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeReset #MidlifeSabbatical #MidlifeGapYear #SecondAct #LifeAfter50 #CareerBreak #SabbaticalLife #WorkLifeBalance #RetirementRedefined #PersonalGrowthJourney #EmptyNestLife #ReinventYourLife #MidlifeTransformation #PurposeAfter50 #ChipConley

Most of us try to solve midlife. What if that’s exactly the wrong approach?

In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “figuring it all out.”

Instead of chasing the right answer, Bill and Dave invite us to prototype our way forward gently, curiously, and without fear of getting it wrong.

Key insights from the conversation:

• Midlife isn’t a crisis. It’s a chrysalis, a space for becoming
• There is no single “right” life, only many good lives you can design
• Stop solving your life and start prototyping small experiments
• Curiosity matters more than certainty
• Meaning isn’t found in big answers, but in everyday moments of flow

This is a hopeful, grounding conversation for anyone who feels stuck, restless, or quietly ready for what’s next.

👉 Click to watch and discover how to design the next chapter of your life without pressure, panic, or pretending.

Timestamps:

03:48 What Designing Your Life is

06:55 What is design thinking

09:22 Designing yourself as a wicked problem

10:20 Gravity problems and anchor problems

12:32 Opening the aperture of choice

14:03 Applying design thinking to midlife

16:49 Creativity and reinvention after success

18:03 Are midlifers more stuck than younger people

19:14 Permission to change in midlife

21:50 Prototyping your next chapter

24:08 Self-criticism fear and resistance

25:00 Learning to be incompetent again

27:49 Personal midlife transitions

31:14 Dark night of the soul

36:53 Introducing the meaning book

38:11 Designing meaning in everyday life

40:21 Redesigning midlife as a culture

44:01 Rethinking work and education

48:25 Reframing midlife identity

52:07 Wisdom bumper stickers

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #DesignYourLife #MidlifeTransition #FindingPurpose #SecondHalfOfLife #LifeDesign #MidlifeMeaning #PersonalGrowth #MidlifeReinvention #DesignThinking #CareerTransition #CuriosityMindset #ModernElder #MidlifeWisdom #LifeAfter40

Real growth rarely happens when life feels comfortable. It begins when we slow down, question our patterns, and face the deeper truths about how we live and lead.

In this episode of Midlife Chrysalis, Chip Conley talks with Diana Chapman, leadership coach and co-author of The 15 Commitments of Conscious Leadership. Drawing from decades of coaching founders and CEOs, Diana shares practical wisdom on how awareness can transform relationships, leadership, and personal growth.

In this conversation, she explores:

• How the Drama Triangle fuels conflict and how to step out of it
• Why playfulness is essential in long-term relationships
• The difference between your zone of excellence and your zone of genius
• Why midlife transformation often requires quiet and surrender

The episode also turns deeply personal as Chip reflects on mortality, purpose, and stepping away from constant busyness to reconnect with what matters most.

Watch the full episode to explore what a true midlife chrysalis can look like.

Timestamps:

03:43 Diana’s path to conscious leadership

07:37 Teach the Class tool

09:03 The Drama Triangle explained

10:43 Personas and playful awareness in relationships

12:31 Lessons from a 44-year marriage

14:32 The 15 Commitments of Conscious Leadership

16:55 Conscious leadership in today’s polarized world

17:53 The new book No Drama Teams

22:05 Trust vs threat in team dynamics

24:26 Coaching leaders through crisis

27:53 What makes a great coach

33:10 Discovering your zone of genius

36:28 Diana’s midlife chrysalis experience

39:42 Chip’s idea for a “month of dying” retreat

44:20 Lessons from a founder facing death

46:04 The value of fallow ground and quiet time

47:18 Designing a life of aliveness

48:36 Wisdom vs knowledge in the age of AI

49:26 Diana’s wisdom bumper sticker

50:21 Childhood truth and trusting your inner knowing

52:30 Reflections on truth, growth, and love

55:17 Closing reflections and invitation to the workshop

Learn more about MEA at ⁠https://www.meawisdom.com/

#DianaChapman #ConsciousLeadership #15CommitmentsOfConsciousLeadership #DramaTriangle #ConsciousLeadershipGroup #ZoneOfGenius #LeadershipCoaching #ConsciousLeadershipTools #NoDramaTeams #LeadershipMindset #EmotionalIntelligence #SelfLeadership #LeadershipTransformation #ConsciousLiving #MidlifeChrysalis

The drive that made you successful may not be meant to lead you forever.

In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens when achievement stops being enough.

In this conversation, you’ll learn:

• Why ego builds the first half of life but can limit the second
• How to move from performer to elder
• What generativity really means
• Why awe and space are essential for soul growth

If you’ve felt a quiet nudge that there’s something deeper beyond success, this episode will resonate.

Tune in and consider who’s driving your life now.

Timestamps:

01:13 Gehl’s Proud Dad Moment

04:17 Enneagram and Early Identity

06:20 Coming Out and Authenticity

09:40 The Ballroom Dance Metaphor

11:47 Richard Rohr and Falling Upward

14:14 Living Stuck in Ego

15:24 Ego, Generativity, and Aging

18:22 From Frontman to Guide

19:30 Reincarnation & Evolving Conciousness

21:32 Where People Get Stuck

25:07 Spirituality & Seeking Awe

26:06 Practices to Soften the Ego

27:26 Richard Rohr Workshop in Santa Fe

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeCrisis #MidlifeTransformation #FindingPurpose #LifeAfter50 #PersonalGrowth #SpiritualGrowth #SelfDiscovery #IdentityShift #PurposeDrivenLife #EgoVsSoul #SecondHalfOfLife #MeaningInLife #InnerGrowth #ModernElder #MidlifeAwakening

What if the real key to longevity isn’t a biohack but a wake-up call?

In this episode, Dr. Brad Jacobs, longevity expert, integrative medicine pioneer, and former UCSF professor, shares what truly helps us thrive in midlife.

After losing his father to cancer at 27, Brad made it his life’s work to understand how we can live longer and better.

In this episode, we explore:

• What actually extends your life (and what’s a distraction)
• Why sleep and stress matter more than most supplements
• How psychedelics are reshaping emotional healing
• What modern masculinity has to do with longevity
• Why midlife is a powerful reset, not a decline

If you’re in your second half and ready to live with more vitality, clarity, and purpose, this conversation will challenge and inspire you.

Press play! Your midlife upgrade starts here.

Timestamps:

04:10 Martial arts to longevity medicine

08:58 Rethinking US healthcare

11:26 Integrative health in midlife

14:42 Sleep optimization and wearables

18:02 Longevity myths and overtraining

19:13 Food philosophy and Blue Zones

21:59 Stress overload and chronic disease

25:50 Love, partnership and second chances

29:57 Psychedelic medicine and ketamine

35:11 Ketamine vs. Psilocybin

37:45 Modern masculinity redefined

41:08 Chip on coming out & courage

48:50 Live Longer Age Better workshop

50:28 Wisdom Bumper Sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#Longevity #MidlifeHealth #HealthyAging #IntegrativeMedicine #LiveLonger #PsychedelicTherapy #KetamineTherapy #ModernMasculinity #MidlifeReset #SleepOptimization #BlueZones #EmotionalHealth #Biohacking #PreventChronicDisease #MidlifeTransformation

In this episode of Midlife Chrysalis, poet and philosopher David Whyte explores why midlife often feels like losing your way and why that experience may be exactly what opens the door to deeper meaning.

Drawing on poetry, psychology, and Dante’s famous “dark wood,” David explains how moments of uncertainty can become powerful turning points in our lives.

In this conversation, he shares:

• Why midlife can feel like exile from your old life
• What Dante’s “dark wood” teaches about transformation
• Why silence and the unknown are essential for growth
• How vulnerability and grief can lead to wisdom

If you’ve ever felt lost, stuck, or questioning the direction of your life, this conversation offers a powerful new way to see it.

👉 Watch the full episode and discover why getting lost in midlife might be the beginning of something greater.

Timestamps:

02:29 What “Midlife Chrysalis” Really Means

06:37 Dante and the Exile of Midlife

13:00 Aging, Eldership and the Inner Horizon

17:40 The Power of Silence and Contemplation

22:55 Poetry, Discipline and Inner Transformation

27:01 Why People Turn to Poetry in Midlife

33:13 Masculinity, Friendship, and Emotional Isolation

37:39 Work as a Spiritual Pilgrimage

44:22 The First Step to Deeper Conversations

50:00 Friendship with the Unknown

52:30 Vulnerability, Care, and Asking for Help

55:09 Wisdom Learned Between 50 and 70

58:27 Final Reflections on Caring and Presence

Learn more about MEA at ⁠https://www.meawisdom.com/

#midlifecrisis #midlifetransformation #midlifeawakening #midlifejourney #personalgrowth #selfdiscovery #lifeafter40 #lifeafter50 #purposeinlife #innertransformation #philosophyoflife #poetryandwisdom #dantesinferno #spiritualgrowth #meaningoflife