Education

The Midlife Chrysalis

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.

Latest Episodes:

From Breakdown to Wholeness: The Hero’s Path Through Midlife with Ben Katt Jan 05, 2026

Show notes

Have you ever reached a point in life where what once worked… suddenly doesn’t?

In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are.

In this episode, you’ll discover:

- Why midlife often feels disorienting, even when life looks “successful” on the outside

- How releasing familiar identities creates space for deeper purpose and wholeness

- Why stillness, reflection, and meditation are essential during times of change

- How community and support help us move through transitions with more easy

If you’re feeling restless, uncertain, or quietly asking “What’s next?”, this conversation offers clarity, comfort, and a sense of direction.

👉 Watch now and explore what this chapter of your life is gently calling you toward.

Timestamps:00:35 The Hero’s Journey and The Way Home

04:49 Ben’s five-year soul journey

07:20 Achievement perfectionism and people pleasing

09:44 Meditation and inner balance

13:19 Phase 1: Leaving the familiar

15:46 Phase 2: Falling into the unknown

18:30 Dark night of the ego

20:51 Wander in the wild

23:56 Support and community

29:52 Phase 3: Rising to wholeness

33:46 Stillness and begin again

38:58 Teaching wisdom without religion

44:13 The wisdom well metaphor

47:21 Why wisdom matters now

50:28 Wisdom bumper sticker

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

Find Ben Katt at https://benkattofficial.com/

#MidlifeTransition #MidlifeCrisis #MidlifeTransformation #HeroJourney #FindingPurpose #MidlifeWisdom #LifeTransitions #PersonalGrowth #MidlifeAwakening #SecondHalfOfLife #InnerWork #MeaningInMidlife #JosephCampbell #WisdomTraditions #MidlifeChrysalis

Jeff Krasno & Schuyler Grant: What Midlife Health Really Requires Jan 02, 2026

Show notes

What if the wellness advice you followed for years stops working after 50?

In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age.

With decades spent in yoga, wellness festivals, and lived experience, they share what actually matters now.

They share insights on:

- Why yoga alone isn’t enough after 50

- How muscle and strength shape metabolic and brain health

- The importance of diverse movement, not extremes

- How simple habits and presence support long-term well-being

This is a grounded, honest conversation about aging well — without hype or shortcuts.

👉 Watch now and rethink what midlife wellness really requires.

Timestamps:

01:22 Skylar’s yoga studio near Ground Zero

05:54 The origins of Wanderlust

09:47 Early resistance to the festival idea

11:28 Wellness hotels and business travel

14:32 Challenges of working with a spouse

20:52 What wellness means after 50

20:52 Muscle, metabolism, and aging

26:30 Yoga versus strength training

29:43 Muscle health and brain health

31:37 Diversity of movement in midlife

34:38 Curiosity, learning, and discomfort

37:34 Habit stacking explained

40:27 Wellness and politics

45:49 Upcoming Baja workshop

49:27 Wisdom bumper stickers

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

#WellnessAfter50 #MidlifeWellness #HealthyAging #StrengthAfter50 #MuscleAfter50 #AgingWell #Over50Health #MidlifeHealth #LongevityLifestyle #FunctionalFitness #WellnessPodcast #HealthyMidlife #MindBodyHealth #HabitsForHealth #LifeAfter50

Stop Starting Over: How to Build Habits That Actually Last Dec 31, 2025

Show notes

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone.

In this episode, you’ll learn:

- Why most resolutions fail

- How habit stacking makes change automatic

- The “Four Ps” that make goals stick

- Why public accountability matters

- How to build habits that last beyond January

If you’re done repeating the same resolutions every year, this episode will help you do it differently.

👉 Watch now and start the year with habits that actually stick.

Timestamps:

00:44 Morning people and Baja midnight

01:39 Why New Year’s resolutions fail

02:07 Common resolutions and lack of a plan

03:30 Habit stacking explained

05:10 Turning resolutions into daily practice

06:10 The four Ps framework

07:45 Pairing and social accountability

08:39 Passion versus accountability

09:50 Why fewer goals work better

11:03 Learning from past resolutions

11:50 Personal resolutions and alcohol

13:10 Family time as a long-term priority

14:14 Final reflections for 2025

15:02 Age, milestones, and perspective

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

#NewYearsResolutions #HabitBuilding #HabitsThatStick #PersonalGrowth #MidlifeWisdom #BehaviorChange #GoalSetting #Accountability #HabitStacking #Mindfulness #SelfImprovement #Longevity #Wellbeing #LifeDesign #WisdomWednesday

Why Transitions Break Us and Heal Us | Kari Cardinale Dec 29, 2025

Show notes

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next.

In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to navigate them is an essential life skill. Through her work on Transitional Intelligence, Kari shares what’s really happening during midlife change and how to move through it with greater clarity and confidence.

You’ll learn:

• Why most midlife “crises” are actually misunderstood transitions

• The three stages of change: endings, the messy middle, and new beginnings

• Why the messy middle feels so hard — and why it matters

• How rituals, community, and small “glimmers” guide what comes next

If you’re feeling stuck or sensing a shift in your life, this episode will help you understand where you are and how to move forward.

👉 Navigating Transitions online course from Modern Elder Academy offers a supportive, step-by-step way to work through change with clarity and confidence, starting March 2: https://www.meawisdom.com/navigating-transitions-online/

Timestamps:

01:20 What is transitional intelligence

03:58 The three stages of transition

06:02 Voluntary and involuntary change

08:02 Why transitions take longer than we expect

11:50 The role of ritual in midlife

15:54 The messy middle and uncertainty

17:53 Glimmers and new beginnings

21:44 Growth mindset in midlife

24:28 Kari’s personal transition story

28:37 The birth of Modern Elder Academy

31:36 Love and relationships in midlife

34:48 What truly gets better with age

37:23 Building community and belonging

42:31 Wisdom bumper sticker

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

#KariCardinale #MidlifeTransitions #MidlifeChange #MessyMiddle #LifeTransitions #PersonalGrowth #MidlifeWisdom #ModernElder #TransitionalIntelligence #EmotionalIntelligence #MidlifePurpose #NewBeginnings #GrowthMindset #MidlifeJourney #InnerWork

From Skateboarding Icon to Modern Elder: Stacy Peralta Dec 26, 2025

Show notes

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity.

Rather than chasing security or certainty, Stacy reveals why reinvention requires becoming a beginner again and why midlife may be the most powerful time to do it.

In this conversation, Stacy explores:

- Why holding onto past identities quietly blocks your future

- How embracing vulnerability and being a “kook” unlocks growth

- The difference between loving something and knowing when to let it go

- How intuition, not logic, often guides the most meaningful transitions

- Daily practices that keep creativity, curiosity, and vitality alive

👉 Watch the full episode now and discover why letting go might be the most powerful move you can make.

Timestamps:

00:58 Early life mischief and finding skateboarding

03:32 Understanding transitions and success

05:57 Realizing it was time to leave skateboarding

06:38 Becoming a beginner in filmmaking

10:46 Family influence and unconventional paths

13:16 Work ethic creativity and self reliance

15:19 Learning from surfer elders

16:59 Following what you love in midlife

18:41 Giving your gift and letting it go

20:00 Embracing vulnerability and being a kook

24:10 Facing fear of being too old

28:00 Flow challenge and skill

31:10 MEA workshops experience

34:25 Quiet rebellion and midlife dreams

37:05 Listening intuition and creating space

39:05 Letting go of control

41:23 Daily practices for vitality

42:46 Harmonizing heart and mind

43:07 The power of listening

44:51 Closing reflections and gratitude

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

#StacyPeralta #MidlifeReinvention #ModernElder #PersonalReinvention #MidlifeTransition #GrowthMindset #CreativeLife #LettingGo #SecondAct #PurposeInMidlife #LifeTransitions #DogtownAndZBoys #SkateboardingLegend #BecomingABeginner #Intuition

The Success Treadmill Is Real: Here’s How to Escape Dec 24, 2025

Show notes

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.”

Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied.

In this conversation, you’ll learn:

- Why success can feel addictive but never fulfilling

- The crucial difference between happiness and joy

- How a simple gratitude practice can change how life feels day to day

- What midlife teaches us about meaning, ego, and impact

Thoughtful, honest, and deeply human, this episode is an invitation to pause, reflect, and reconnect with what actually matters.

👉 Watch now and step off the success treadmill.

Timestamps:

01:00 Holiday plans and family time

01:51 MEA Film Festival vision and growth

04:28 Defining success and ambition

06:30 Happiness vs. Joy

10:03 Making gratitude intentional

11:27 Realizing the success treadmill

15:21 Ego shift at Airbnb

16:32 Getting off the treadmill sooner

16:50 Near death experience and perspective

18:30 Service as gratitude practice

19:40 Facing illness and loss

21:33 This too shall pass

21:49 Collective gratitude and closing

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

#SuccessTreadmill #GratitudePractice #MidlifeWisdom #FindingMeaning #HappinessVsJoy #PersonalGrowth #MidlifeTransformation #RedefiningSuccess #LifePurpose #InnerFulfillment #ChipConley #MidlifeCrisis #SelfReflection #LifeLessons #MindfulLiving

The Hidden Cost of Playing It Safe in Midlife | Dr. Margie Warrell Dec 22, 2025

Show notes

What if the real risk in midlife isn’t change but staying comfortable?

In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Warrell, global expert on courage and bestselling author of The Courage Gap, to explore why so many smart, capable people feel stuck and how to move forward with clarity and bravery.

Drawing from her journey from a rural Australian farm to the world stage, Margie shares powerful insights on courage, reinvention, and choosing growth over safety.

In this episode, you’ll learn:

- Why comfort quietly keeps you stuck

- The hidden “timidity tax” of playing it safe

- The tension between belonging and becoming

- Why courage is a decision, not a feeling

- Simple ways to take braver action in midlife

If you’re ready to stop circling what’s familiar and start stepping into what’s possible, this conversation is for you.

🎧 Watch now and choose courage over comfort.

Timestamps:

00:05 Meet Margie Warrell

01:08 Margie’s rural upbringing

02:33 The horse story and learning courage

05:00 Traveling the world after university

06:33 Early adulthood and global moves

08:47 Trauma, healing, and transformation

09:51 Life now and current work

11:05 Why courage is difficult

13:26 Becoming versus belonging

16:40 Regret and missed chances

21:19 Courage as action, not feeling

23:42 Closing the courage gap

23:42 Reset your focus

29:10 Challenge your certainty

33:50 Take the chance

36:13 Real-life courage breakthroughs

39:05 Courage, anxiety, and connection

42:34 Wisdom bumper sticker

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

#MidlifeCrisis #CourageOverComfort #PersonalGrowth #LifeTransitions #MidlifeReinvention #LeadershipMindset #SelfDevelopment #EmotionalResilience #FindingPurpose #SecondHalfOfLife #FearAndGrowth #AuthenticLiving #WomenInLeadership #BraveLiving #TheCourageGap

Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald Dec 19, 2025

Show notes

Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you.

In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel reframes dating not as luck but as a learnable skill, especially in midlife.

Together, we explore:

- Why the people who make us happiest don’t always match our dating checklists

- How chemistry can fool us and what actually leads to lasting connection

- The quiet dating rules that keep smart people single

- Why love often shows up in unexpected packages

- How modern couples are redefining partnership, including living apart together

This is a hopeful, practical conversation about dating with wisdom, curiosity, and openness, not fear or frustration.

👉 Listen or watch now and discover why midlife may be your most meaningful, and romantic, chapter yet.

Timestamps:

00:46 Meet matchmaker Rachel Greenwald

03:36 From Harvard MBA to professional matchmaker

04:03 A midlife pivot that changed everything

07:29 The highs and lows of matchmaking

09:44 What is keeping people single

10:20 The most powerful question in dating

13:11 Chemistry vs compatibility & happiness

17:11 Why we repeat unfinished relationship patterns

19:46 Why dating checklists can backfire

22:39 Why men make up most matchmaking clients

25:08 Why parents hire matchmakers for young adults

28:03 Why midlife dating isn’t hopeless

35:57 The three must-haves that really matter

38:26 Living apart together and modern relationships

44:51 Inside the Santa Fe dating workshop

48:27 Wisdom bumper sticker

53:11 Final takeaways on love and dating in midlife

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

#MidlifeDating #DatingAfter40 #DatingAfter50 #MidlifeRelationships #FindingLoveLaterInLife #DatingAdvice #ModernDating #RelationshipAdvice #DatingWisdom #MidlifeWomen #MidlifeMen #Matchmaking #LoveAfterDivorce #DatingOver40 #MidlifeChrysalis

Inside the Messy Middle: What Actually Drives Transformation in Midlife Dec 17, 2025

Show notes

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.

In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.

Chip shares:

• The three stages of every transition and where most people get stuck

• What really happens inside the messy middle

• Why men and women experience midlife so differently

• How transitional intelligence (TQ) helps you move forward with clarity

If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need.

If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights.

Timestamps:

00:00 Film Festival & Holiday Mood

01:55 Crisis vs Chrysalis and the Hollywood Myth

05:15 The Three Stages of Transition

07:07 Emotions in the Messy Middle

09:33 Finding Your Through Line

11:21 Ritualizing Endings

13:16 How Men Experience Midlife

15:40 How Women Experience Midlife

15:53 Why Women Navigate Midlife Differently

19:27 Identity, Purpose, and Feeling Stuck

21:35 Chip’s Personal Midlife Story

22:42 Why Men Resist This Work

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

#MidlifeChrysalis #MidlifeTransition #MidlifeCrisis #MessyMiddle #PersonalGrowthJourney #LifeTransitions #ChipConley #TransitionalIntelligence #MidlifeWisdom #SelfDiscovery #MidlifeWomen #MidlifeMen #EmotionalWellbeing #LifeReinvention #GrowthMindset

Michael Clinton on Life Layering: How to Build a Richer Life After 50 Dec 15, 2025

Show notes

What if midlife became your chance to ROAR, not retire?

In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how reinvention is not only possible, it’s essential.

He breaks down the ROAR framework for reimagining your future, explains why “life layering” is the antidote to midlife crisis, and dives into the emerging world of longevity science, age-positive culture, and purpose-driven living. If you’ve ever wondered what’s next, or what’s possible, this episode shows you how to build a richer, more meaningful second half of life.

Watch now and start reimagining what your future can be.

Timestamps:

00:00 Michael’s Santa Fe moment

01:31 Early life, father’s influence, love of words

05:27 A career in publishing

08:02 Midlife awakening at 39

10:50 Climbing Kilimanjaro and building an adventurous life

12:32 Returning to school at 67

15:56 The ROAR framework begins

20:00 Ageism, language shifts, modern role models

25:13 Life layering and building new identities

27:45 Preparing for post-career life

29:01 Reinvention stories and reimagineers

30:51 Relationships, editing your circle, and support systems

35:25 Growth mindset and lifelong curiosity

37:33 Longevity insights and the next book

39:18 Why longevity is having a cultural moment

44:01 Why the US is falling behind on lifespan

45:22 Rethinking work, age diversity, and longer careers

49:56 Longevity clinics and new health models

52:57 Longevity travel and residential communities

54:35 Wisdom bumper sticker

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

#MidlifeReinvention #Longevity #PurposeAfter50 #ReimaginingAging #LifeLayering #ROARMethod #SecondHalfOfLife #HealthyAging #MidlifeAwakening #RewireNotRetire #AgingWell #LiveLongerBetter #MidlifeTransformation #ModernAging #LifelongLearning

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