Ever notice how some friendships don’t end, they just stop deepening?You still care about each other, but the conversations feel thinner than they used to. In midlife, that quiet shift is more common than we admit.

In this Wisdom Wednesday episode, Chip Conley, founder of MEA, joins Derek Gehl for a warm, honest conversation about friendship in the second half of life: why it changes, why it matters more than ever, and how it can grow again.

What you’ll take away:

• Friendship is a practice, not a personality trait
• Most of us outgrow conversations, not people
• Depth and vulnerability create real connection
• Reaching out — even after years — can reopen meaningful bonds

If you’ve ever wondered how to build friendships that actually nourish you as you age, this conversation is for you.

Listen now and discover how midlife friendships can become richer, not smaller.

Timestamps:

00:13 Friends in midlife and outgrowing friendships

00:45 Friendship as a practice

02:10 Reconnecting with old friends

04:20 Outgrowing conversations not people

06:00 Depth vulnerability and the three vaults

09:40 Why friendship requires depth

10:48 Men opening up emotionally

13:05 Leading with vulnerability

13:58 Creating deeper conversations naturally

15:48 Different levels of friendship

16:39 Couples growth and shared language

17:37 Transactional vs real friends

18:02 How to rebuild friendships in midlife

20:13 Closing thoughts and wrap up

Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeFriendships, #MidlifeConnection, #FriendshipAfter40, #SecondHalfOfLife, #MeaningfulRelationships, #EmotionalIntelligence, #PersonalGrowth, #SocialConnection, #AuthenticLiving, #MidlifeWisdom, #LifeTransitions, #ProAging, #ModernAging, #HumanConnection, #WisdomWednesday

Ever wonder what happens when “success” still feels empty?

At 47, Greg Scheinman looked like he had it all, career, family, success, yet felt completely lost. That moment pushed him to reinvent himself and create Midlife Male, a movement helping men find purpose, strength, and authenticity in midlife.

In this episode, we dive into what modern masculinity really means, why so many men struggle with identity and purpose, and how to turn a midlife crisis into a life by design.

Tune in to learn how Greg turned breakdown into breakthrough and how you can too.

Timestamps:

00:00 Introduction

00:24 Early Life & Family Loss

02:38 Working for Harvey Weinstein

05:03 From Film to Entrepreneurship

08:15 Lessons on Curiosity & Reinvention1

0:53 Identity Crisis at 40

13:29 Entering the Insurance Industry

15:16 Building a PBS Show

16:57 Struggling with Identity

22:20 Tipping Point at 47

24:33 Creating Midlife Male

26:30 Marriage Problems & Masculinity

30:34 Why He Built Midlife Male

38:48 The Modern Midlife Male Dilemma

41:37 Conviction, Curiosity & Courage to Speak

45:00 The Six F’s of Life & Finding Success

49:06 Raising Sons Today

54:56 Wisdom Bumper Sticker

57:07 Learning to Be Both Hard & Soft

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

#GregScheinman #MidlifeMale #MidlifeChrysalisPodcast #ChipConley #ModernMidlifeMan #MenInMidlife #MidlifeReinvention #MidlifeIdentity #MensMentalHealthAwareness #RedefiningMasculinity #LifeByDesign #EntrepreneurInMidlife #MidlifeWisdom #PurposeBeyondSuccess #FromCrisisToGrowth

Midlife rarely falls apart all at once. It slowly grows quieter, fewer close friendships, less community, more doing and less belonging.

In this episode of Midlife Chrysalis, Jeff Hamaoui, MEA co-founder and community builder, reflects on how midlife invited him to redesign his life around friendship, connection, and community.

In a warm, thoughtful conversation, Jeff shares:

- Why friendship is a skill we can practice and deepen

- How transactional living erodes real connection

- Why community is essential to well-being in midlife

- How choosing a second chapter starts with belonging

If you’re navigating midlife and craving deeper connection, this episode offers clarity, comfort, and perspective.

👉 Watch now and explore what truly supports your next chapter.

Timestamps:

03:16 Jeff’s background and international upbringing

05:02 Growing up in Venezuela and reflections on the country

06:38 Leaving the Bay Area and the midlife turning point

09:56 Comparison culture and pressure in the Bay Area

11:02 Transactional vs relational relationships

12:39 Friendship as a practice

15:44 Core lessons on listening and asking better questions

18:49 Going first and the mindset of friendship

22:14 Friendship health longevity and happiness

24:23 Resistance to wellness and personal growth

28:44 Self-awareness pattern recognition and wisdom

31:46 Midlife transitions and choosing a second adulthood

38:10 Midlife crisis vs midlife chrysalis

40:29 MEA as a call to action

43:55 Creating community and the origins of Baja Sage

45:09 Community vs real estate development

51:23 Social architecture and relational living

52:32 Wisdom as metabolized experience

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

#friendshipasaskill #midlifecommunity #relationalliving #secondadulthood #midlifefriendship #communitybydesign #transactionaltorelational #modernelder #mea #chipconley #jeffhamaoui #intentionalcommunity #midlifebelonging #socialconnection #humanconnection

Most of us grow up thinking mentorship means having the answers. In midlife, we learn it’s really about asking better questions.

In this Wisdom Wednesday episode, Derek and Chip explore how mentorship evolves when experience meets curiosity. Drawing on stories from Airbnb, intergenerational leadership, and lessons from unlikely teachers, Chip shows why the best mentors are still learning.

In this conversation, you’ll discover:

• Why great mentorship is a two-way exchange, not top-down advice

• How modern elders learn alongside younger generations

• The difference between a librarian mentor and a confidant mentor

• Why respect and curiosity matter more than credentials

• How asking the right questions creates real growth at work and in lifeIf you’re navigating midlife, leading across generations, or rethinking how you share your wisdom, this episode is for you.

Watch now and join us for Wisdom Wednesday.

Timestamps:

01:58 Why mentorship matters in midlife

04:16 Digital natives vs digital immigrants

05:11 The respect gap in mentorship

06:20 Defining wisdom and lived experience

07:10 Four stages of becoming a modern elder

08:22 Appreciative inquiry and powerful questions

10:30 Librarian mentor vs confidant mentor

12:20 Chip Conley and Herb Kelleher mentorship story

14:20 How confidant mentorship builds confidence

15:45 How to structure a healthy mentorship

16:53 Mentors vs coaches explained

18:35 The mentorship gap and retention impact

18:51 How to start mentoring at midlife

20:55 Mentorship and renewed purpose

21:51 Final reflections and closing

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

We’re surrounded by information but many of us still feel unsure about how to live well.

This episode gently explores why midlife pulls us toward wisdom, not more answers. Chip Conley is joined by bestselling author Eric Weiner (The Geography of Bliss, Man Seeks God, The Socrates Express), a curious guide who’s spent years learning from philosophers, cultures, and lived experience. Together, they talk about what ancient wisdom can teach us about modern life—especially when certainty starts to fall away.

In this conversation, you’ll hear:

• Why midlife naturally turns us into philosophers
• The difference between knowing more and living better
• How thinkers like Socrates, Thoreau, and Marcus Aurelius offer practical guidance
• Why wonder, humility, and generosity matter more than expertise
• Simple ideas that help us navigate change, relationships, and uncertainty

This is a warm, thoughtful, and often playful conversation about slowing down, asking better questions, and learning how to live with more clarity and meaning.

Watch now and step into the wisdom midlife is inviting you to explore.

Timestamps:

04:21 Welcome to Midlife Chrysalis

04:59 Writing with humility and vulnerability

07:02 Book titles and framing ideas

08:34 Geography of Bliss origin story

12:31 Favorite places and soul place

13:54 Ben Franklin and usefulness

18:31 Writing about God and belief

21:44 Geography of Genius and creativity

23:30 Introducing The Socrates Express

24:10 Knowledge vs wisdom

27:23 What philosophy really is

30:38 Wonder vs curiosity

34:40 Stoicism and modern relevance

37:33 Philosophers that resonated most

40:53 Thoreau and learning how to see

44:52 Why philosophy matters in midlife

49:20 Wisdom bumper stickers

52:26 Closing and Santa Fe workshop

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

What if losing everything was the only way to truly find yourself?

MIT lecturer and artist Aithan Shapira shares how the collapse of his art career became the catalyst for profound reinvention.

He explains why midlife isn’t about decline but transformation , a time to practice letting go, reframe purpose, and reconnect with what matters most.

If you’re in a season of change, this episode will help you see midlife as your greatest canvas yet.

Timestamps:

00:00 Intro

01:17 Meet Aithan Shapira

04:05 Living Between Worlds

05:32 MIT, NASA & Global Clients

06:32 Practice as a Core Principle

07:46 Cubism & Midlife Transition

11:00 Life as a Practice vs Routine

14:05 Practice vs. Ritual

15:30 Aithan’s Views on Midlife

20:55 Accelerating Internal Change

25:37 The Three Stages of Transition

27:59 Coping With Freefall

32:59 What Needs to Be Preserved

36:11 Identity in Retirement & Second Half of Life

38:18 Aithan’s Own Chrysalis Story

46:21 Long Life Learning

53:21 The Wisdom of Midlife

55:58 Aithan’s Bumper Sticker Wisdom

59:07 Closing Thoughts

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

What if midlife isn’t the end of your career story but the smartest place to rewrite it? In this episode of Wisdom Wednesday, Chip Conley joins Derek Ghel to unpack what really happens when people feel stuck at midlife, and why career change after 50 doesn’t require starting over or burning everything down.

Drawing on his journey from boutique hotels to Airbnb to founding the Modern Elder Academy, Chip offers a grounded, hopeful roadmap for reinvention that actually works in the real world.

In this episode, you’ll learn:

• Why midlife can be the most strategic time to change careers, not the riskiest
• How to use small, iterative steps and bridge jobs instead of all-or-nothing leaps
• The four pathways to purpose that reveal what’s next for you
• Why portfolio careers and encore paths are becoming the new normal
• How identity, fear, and “being a beginner again” shape midlife transitions

If you’re questioning your work, your direction, or what the next chapter should look like, this conversation will help you reframe what’s possible.

Watch the episode, reflect on what’s calling you next, and take the first small step forward.

Timestamps:

00:41 Chip Conley’s career journey

03:10 Rethinking age and career length

05:23 Retirement vs staying relevant

10:43 Taking small iterative steps

13:25 Entrepreneurship after 50

16:33 Bridge jobs and testing ideas

18:26 A real midlife pivot story

19:18 Purpose, community and wellness

23:29 Identity fear and becoming a beginner

27:17 Why people come to MEA

31:47 Final thoughts and wrap-up

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

He had everything going for him, until his body shut him down on live TV.

In this episode, Dan Harris sits down with Chip Conley for a warm, honest conversation about ambition, anxiety, and what really changes in midlife. Dan opens up about the panic attack that forced him to slow down, his years inside high-pressure newsrooms at ABC, and the quiet realization that productivity, without presence, was costing him more than it gave. What follows is not a polished mindfulness pitch, but a deeply human reflection on letting go, growing wiser, and redefining success in the second half of life.

In this conversation, you’ll hear Dan reflect on:

• Why anxiety and ambition are often two sides of the same coin
• How meditation helped him step out of the productivity trap—not optimize it
• What he had to release after becoming outwardly “successful”
• Why midlife is better understood as a chrysalis, not a crisis
• How relationships, presence, and character shape a more meaningful future

If you’re navigating midlife, questioning old definitions of success, or simply craving a more spacious way to live, this conversation will feel like sitting down with two thoughtful friends who’ve been there. Watch now and join the conversation.

Timestamps:

02:17 Defining midlife and Dan Harris’s journey

03:50 Panic attack on live TV

05:31 From panic attack to meditation

06:46 Family background and anxiety

08:31 Decade between crisis and mindfulness advocacy

09:33 Therapy spirituality and discovering meditation

13:37 Writing 10% Happier

14:22 Origin of the 10% happier idea

16:43 Science and benefits of meditation

19:47 Skepticism identity and cognitive dissonance

22:14 Life after the book’s success

26:06 Productivity versus presence

29:47 Burnout hyper productivity and 360 review

33:06 Letting go of roles and redefining life

35:59 Midlife as chrysalis not crisis

39:36 Favorite meditation practices

42:09 Wisdom midlife and modern elderhood

45:08 Character skills in the age of AI

47:07 Personal wisdom and life lessons

49:10 Closing reflections and goodbye

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