The Midlife Chrysalis

Aging isn’t just about getting older. It’s about discovering who you are when the roles that once defined you begin to fall away.

In this episode, Chip Conley sits down with Connie Zweig, author of The Inner Work of Age, to explore the deeper psychological and spiritual work of midlife and beyond.

Connie shares what it takes to move from simply growing old to becoming an elder, including:

• Moving from role to soul: Why identity built around achievement and productivity may need to loosen as we age.
• Meeting your shadow: How the parts of ourselves we ignore can surface during major life transitions and shape our choices without us realizing it.
• Listening to the unlived life: Why buried desires, abandoned paths, and old patterns often reappear at midlife.
• Learning to let go: How releasing outdated roles, beliefs, relationships, and attachments can make space for a new stage of life.
• Accepting impermanence: What Connie has learned in her 70s about mortality, control, self-reflection, and living more consciously.

This is a thoughtful conversation about aging not as decline, but as a profound inner transition.

Watch now and discover what it means to move from role to soul.

Timestamps:

(02:40) Growing and Aging Throughout Life

(08:17) Letting Go of Roles and Identities

(10:02) Moving From Doing to Being

(17:28) What Is Shadow Work?

(20:05) From Role to Soul

(23:17) The Unlived Life and Midlife Crisis

(29:14) The Inner Ageist

(31:58) The Chrysalis of Midlife

(34:41) Facing Death and Mortality

(39:37) What Rumi Can Teach Us

(43:35) Wisdom for Younger Generations

(45:40) Impermanence, Control, and Conscious Living

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

#Midlife #ConsciousAging #ShadowWork #MidlifeTransformation #HealthyAging #InnerWork #CarlJung #RoleToSoul #MidlifeCrisis #PersonalGrowth #SelfReflection #AgingWell #SecondHalfOfLife #UnlivedLife #ConnieZweig

Some losses hit harder than we ever expect, and grief doesn’t follow our timeline.

In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the unexpected death of his beloved dog Jamie and what the experience has taught him about grief, love, and loss.

Key insights from the episode:

• Grief comes in waves. It can surface as sadness, anger, exhaustion, or simply the need for space.

• You can’t rush grief. Searching for meaning too quickly can keep us from actually feeling what we’ve lost.
• Grief reveals what we love. The depth of our grief often reflects the depth of the connection.
• Some losses go unacknowledged. Pets, relationships, careers, health, and unrealized expectations can leave grief we never fully allowed ourselves to feel.

Tune in for an honest and moving conversation about the losses we carry, the emotions we can’t control, and why there is no shortcut through grief.

Watch the full episode now.

Timestamps:

(00:00) Welcome to Wisdom Wednesday

(02:10) Remembering Jamie

(07:05) How Grief Comes in Waves

(10:40) The Losses We Don’t Talk About

(11:44) Why Unexpected Loss Hits Harder

(12:54) Finding Ways to Cope With Grief

(13:55) The Danger of Spiritual Bypass

(18:53) You Can’t Force Grief

(19:16) Grief, Anger, and Boundaries

(20:30) Letting Emotions Pass Through

(22:07) An Experiment for Unprocessed Grief

(24:34) Grieving the Losses of Cancer

(26:03) Closing Thoughts

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

#Grief #GriefAndLoss #CopingWithGrief #PetLoss #UnprocessedGrief #GrievingProcess #ChipConley #MidlifeChrysalis #EmotionalHealing #SpiritualBypass #LifeAfterLoss #UnexpectedLoss #GriefJourney #MidlifeWisdom #MEA

What happens when the identity you've spent your entire life building suddenly disappears?

Former South African international cricketer Paul Harris reached the highest level of his sport, but retiring at just 33 forced him into an even bigger challenge: discovering who he was beyond cricket. In this powerful conversation, Paul shares the emotional reality of life after professional sports and the lessons that helped him build a meaningful second chapter.

In this episode, you'll learn:

• Why major life transitions often trigger an identity crisis
• The hidden mental health challenges many high achievers face
• The three principles that helped Paul rebuild his confidence, purpose, and career
• Why the people you surround yourself with can shape your future
• Why "Outwork Everybody" became the foundation of his success

Paul's journey proves that losing one identity doesn't mean losing yourself. Sometimes the end of one chapter is the beginning of a more meaningful one.

If you enjoyed this episode, please like, subscribe, and share it with someone who could benefit from Paul's story.

Timestamps:

(02:46) Meet Paul Harris

(03:44) Early Life and Playing Cricket

(08:36) What is a Spinner?

(10:45) Baseball vs. Cricket

(11:22) Why Cricket Never Caught in the US

(13:15) Why He Retired At 33

(15:00) Losing His Identity After Cricket

(18:24) Life After Fame

(21:14) Starting Over At 40

(22:22) Why Retired Athletes Struggle

(27:01) Advice For Major Life Transitions

(31:30) What Midlife Means To Him

(33:35) Wisdom Bumper Sticker

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

#PaulHarris #LifeAfterSuccess #IdentityCrisis #ProfessionalAthlete #LifeAfterSports #CareerTransition #FindingPurpose #SecondChapter #MentalHealth #HighPerformance #Resilience #PersonalGrowth #SuccessMindset #Cricket #MidlifeChrysalis

Sometimes the most powerful thing we can do is stop doing and simply be present.

In this episode, Chip Conley talks with Teddi Dean, former Bones Brigade skateboarder turned filmmaker, mindfulness teacher, and Head of Mind & Body at MEA.

Teddy shares his journey through sobriety, yoga, meditation, and decades of exploring what it means to live with greater awareness.

You’ll discover:

• Why stillness can be transformative and help us reconnect with ourselves.
• How 10 to 20 minutes of daily mindfulness can change how we respond to life.
• Why mindfulness goes beyond meditation, from walking and surfing to ordinary daily activities.
• How listening to your body and breath can lead to wiser choices.
• Why paying attention makes ordinary life richer and helps us see familiar things with fresh eyes. Teddi’s hard earned wisdom is beautifully simple: Just be.

Watch the full episode for a practical and inspiring conversation about becoming more present for your own life. 

Timestamps:

(00:00) Meet Teddi Dean

(01:05) Growing Up in Skate Culture

(03:03) Joining the Bones Brigade

(05:20) Walking Away From Skateboarding

(08:57) Drinking and Life After Skateboarding

(10:04) Getting Sober at 35

(11:00) Finding Yoga and Mindfulness

(14:23) Starting a New Life in Baja

(17:10) Joining the Modern Elder Academy

(19:04) Why Midlife Needs a Wisdom School

(21:35) The Power of Silent Retreats

(26:49) Learning to Sit With Yourself

(28:39) Building a Daily Mindfulness Practice

(30:22) Creating Space Between Stimulus and Response

(32:01) Turning Everyday Activities Into Mindfulness

(35:05) What Is Embodied Prayer?

(36:30) Listening to the Wisdom of the Body

(39:06) Becoming Amazed by the Mundane

(41:18) Wisdom Bumper Sticker

(43:00) Sunday Sangha 

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

#TeddiDean #ChipConley #ModernElderAcademy #JustBe #PowerOfPresence #MindfulnessInMidlife #SilentRetreat #DailyMindfulness #FromDoingToBeing #MindBodyAwareness #EmbodiedPrayer #MindfulnessAndSobriety #BonesBrigade #FindingStillness #MidlifeWisdom

Happiness and purpose may not be enough for a truly rich life.

In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness and why curiosity, new experiences, challenge, and spontaneity become especially valuable as we age.

You’ll discover:

• Why psychological richness matters as we get older and how curiosity keeps us engaged with life.
• The question that can reshape your next decade: What will you regret not learning, doing, or investing in 10 years from now?
• Why becoming a beginner again matters, from learning a new skill to pursuing a passion you’ve neglected.
• Why spontaneity and stepping beyond routine enrich our lives and open us to experiences we might otherwise miss.

Watch the full episode and choose one thing you’re ready to finally do. 

Timestamps:

(00:02) Welcome to Wisdom Wednesday

(02:23) What Is a Psychologically Rich Life?

(05:58) Creating More Psychological Richness

(10:33) Reinventing Yourself in Midlife

(12:04) What Will You Regret in 10 Years?

(14:33) Is the Door Really Closed?

(16:04) Why We Regret What We Don’t Do

(17:48) Ways to Enrich Your Life

(20:24) Pilgrimages and New Experiences

(21:40) Curiosity and Leaving Your Comfort Zone

(22:08) The Power of Spontaneity

(24:01) This Week’s Challenge24:50 Make Your Commitment Public 

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

#PsychologicallyRichLife #PsychologicalRichness #ChipConley #MidlifeChrysalis #MidlifeReinvention #Curiosity #HealthyAging #LifelongLearning #GrowthMindset #MidlifePurpose #LifeAfter50 #LivingWithoutRegret #NewExperiences #MidlifeTransformation #Longevity

The longevity revolution isn’t coming. We’re already living it, and we’re not ready.

In this episode, David Sinclair of the International Longevity Centre joins Chip Conley to explore what longer lives mean for all of us and why society needs to catch up with a future that’s already here.

In this conversation:

• Why the real longevity challenge isn’t living to 100, but adapting to longer lives today
• Why prevention needs to play a much bigger role in how we approach health and aging
• How longer lives are changing the way we think about work, money, retirement, and our communities
• Why purpose, connection, and staying engaged matter as much as staying healthy
• How the wisdom we accumulate over a lifetime can be shared with the next generation

Watch the full episode for a fresh perspective on longevity and what it will take to make our longer lives healthier, more purposeful, and more connected. 

Timestamps:

(03:13) Why Society Isn’t Ready for Longer Lives

(04:47) Why We Keep Ignoring the Aging Crisis

(07:13) What Governments Must Do About Longevity

(10:14) Why Prevention Should Come First

(12:01) Building Cities for Longer, Healthier Lives

(15:48) The Economics of an Aging Population

(18:09) Rethinking Life for the 100 Year Age

(20:39) Can Human Lifespan Keep Increasing?

(26:13) Living Longer Isn’t Enough

(27:18) Why Purpose Matters as We Age

(31:21) David Sinclair on the Other David Sinclair

(34:53) Who Is Getting Longevity Policy Right?

(37:53) The Responsibility to Pass on Wisdom

(41:04) The Business Opportunity of Longevity 

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

#DavidSinclair #InternationalLongevityCentre #Longevity #AgingSociety #HealthyAging #LongevityEconomy #AgingPopulation #FutureOfAging #PurposefulAging #100YearLife #LongevityPolicy #FutureOfRetirement #PreventiveHealth #AgeFriendlyCities #LifelongLearning

Success can look impressive on the outside and still leave you feeling like something is missing.Seth Streeter, co-founder of Mission Wealth, spent decades building a successful career while constantly pushing himself to achieve more. But after personal crisis, health struggles, and a major identity shift, he began questioning what success was really for.

In this episode, Seth shares his journey from achievement to Life 3.0, a new chapter centered on fulfillment, purpose, and what truly makes us come alive.

Key insights include:

• Achievement can become an identity. When worth is tied to productivity and success, stepping away can be harder than expected.
• Redefining success changes what matters. A fulfilling life requires looking beyond money, status, and conventional measures of achievement.
• Transformation requires letting go. Moving forward often means releasing old roles, habits, and ideas about who we need to be.
• Your values reveal what’s missing. Identifying what matters most can expose the gap between the life you’re living and the life you want.

Tune in for an inspiring conversation about redefining success, finding what makes you come alive, and creating a more fulfilling next chapter. 

Timestamps:

(04:04) Seth’s origin story

(09:12) The cost of relentless achievement

(09:51) Building Mission Wealth

(12:31) When life fell apart

(15:39) Finding a new way forward

(19:50) Wealth vs. fulfillment

(23:16) Leaving the company he built

(27:12) Finding purpose in Life 3.0

(29:30) What keeps people stuck in Life 2.0

(32:45) What makes you come alive?

(33:39) Identifying your core values

(36:01) Love, impact, and health

(38:07) Building deeper human connection

(40:12) Redefining success

Learn more about MEA at ⁠https://www.meawisdom.com/#Life30 #RedefiningSuccess #MidlifeTransformation #MidlifeReinvention #PersonalGrowth #LifePurpose #Fulfillment #FindingPurpose #LifeTransitions #IdentityShift #MeaningfulLife #CoreValues #SelfDiscovery #MidlifeWisdom #SethStreeter

Growing older is changing. Maybe the way we live should change with it.

In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to later life: shared homes that combine independence, connection, and community.

Drawing on MEA’s growing Golden Girls experiment, Chip shares:

• Why traditional senior living and aging in place don’t work for everyone
• What MEA has learned from its first shared homes and Golden Girls retreats
• Why privacy, flexibility, and compromise are essential to making shared living work
• How shared homes can grow into vibrant “distributed villages” built around friendship, learning, and common interests
• How this model could inspire new approaches to housing and community far beyond MEA

Watch the full episode to discover a different way to think about home, community, and growing older.

Timestamps:

(00:00) Welcome to Wisdom Wednesday

(01:39) Rethinking How We Live as We Age

(05:05) The Golden Girls Shared Living Idea

(07:05) Sage House and Chrysalis House

(10:26) The Realities of Shared Living

(12:51) Are You Ready to Live With Others?

(14:46) Bringing the Concept to Other Communities

(16:38) Creating a Distributed Village

(19:09) The Long-Term Vision for MEA Homes

(22:09) What About the Golden Guys?

(23:05) How to Explore Golden Girls Living

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

#ChipConley #WisdomWednesday #ModernElderAcademy #MEA #GoldenGirlsLiving #SharedLiving #AgingWell #HealthyAging #PositiveAging #SeniorLiving #CommunityLiving #LifeAfter55 #Midlife #Longevity #AgingInPlace

What happens when you achieve the success you've worked for... and it still doesn't feel like enough?

In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success.

Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work and leadership, and what it really takes to build a meaningful life in the second half of adulthood.

Key insights include:

• Why success often creates unexpected emptiness
• How AI is changing leadership and work
• The role curiosity plays in personal growth
• Why self-care is a leadership skill
• A powerful question that can help shape your next decade

If you're navigating midlife, rethinking your priorities, or wondering what comes after achievement, this conversation offers practical wisdom for building a more meaningful future.

Watch now and discover what might be waiting on the other side of success.

Timestamps:

(01:14) Meet Edward Sullivan

(02:34) What Makes a Great Coach?

(04:54) AI Anxiety and Burnout

(06:44) Tuning the Instrument

(08:37) Coaching Young Founders

(09:42) Wisdom and Age Diversity

(12:49) Building Intergenerational Teams

(17:16) Curiosity Before Advice

(20:11) Midlife and the Happiness Curve

(22:37) Right-Sizing Expectations

(24:32) Why Success Can Feel Empty

(28:56) The Power of Small Experiments

(32:17) Designing a Meaningful Life

(35:43) Advice for New Coaches

(37:57) The Business of Coaching

(40:16) Finding Your Coaching Niche

(41:32) A Lesson Learned the Hard Way

(43:41) What Now Workshop

(44:18) Building a Career Crescendo

(45:38) Closing Thoughts

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

Workshop with MEA in March 2027: https://www.meawisdom.com/workshop/what-now-finding-passion-and-purpose-after-a-big-success-march-2027/

#LifeAfterSuccess #WhatNow #PurposeAndMeaning #ExecutiveCoaching #LeadershipDevelopment #CareerTransition #PersonalGrowth #MidlifeTransition #SuccessfulButUnfulfilled #SelfDiscovery #MeaningfulLife #ModernElder #ChipConley #EdwardSullivan #VelocityCoaching

Your job title tells people what you do. The problem you care about tells them who you are.

Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life.

Some of the ideas they explore:

• Why following your energy can lead you somewhere a career plan never could
• How becoming a beginner again can bring fresh energy to midlife
• Why learning, earning, and giving back can happen throughout our lives
• What younger generations can teach us about work and purpose
• Why our most human strengths matter even more in the age of AI

From leaving a 20-year career in venture capital to stepping into the vulnerability of teaching and public service, Arun shares why the next chapter doesn’t need to be mapped out before you begin it.

Watch the full episode of The Midlife Chrysalis.

Timestamps:

(03:39) Arun Gupta’s Mission-Driven Journey

(09:05) From India to Venture Capital

(12:50) Why Careers Don’t Follow a Straight Path

(16:28) What Gen Z Is Teaching Us

(20:33) Rethinking Learn, Earn, and Return

(22:33) Finding New Purpose Later in Life

(25:07) What Makes a Great Mentor

(29:24) Learning Across Generations

(33:23) AI and the Future of Work

(36:17) Building Human Capital in the AI Age

(39:25) Arun’s Midlife Career Reinvention

(43:46) What Problem Do You Care About?

(47:24) Doing Good and Doing Well

(49:00) Rebuilding Trust Through Interdependence

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

#ArunGupta #ChipConley #MidlifeChrysalis #TheMissionGeneration #NobleReach #CareerReinvention #PurposeDrivenCareer #MidlifeCareer #FutureOfWork #IntergenerationalMentorship #LifelongLearning #AIAndWork #CareerPurpose #MeaningfulWork #SecondAct