What happens when time stops feeling endless and starts feeling real?

In this episode of Wisdom Wednesday, Chip Conley shares how living with cancer reshaped his relationship with time, purpose, and urgency in midlife.

Joined by Derek Gehl, Chip reflects on cancer scans, mortality, and why remembering that life is finite can actually deepen meaning, not fear.

Together they explore:

• Why memento mori can bring clarity, not darkness
• How midlife urgency is about intention, not panic
• What legacy really means beyond achievement

This is a warm, life-affirming conversation about choosing what matters most when you realize tomorrow isn’t guaranteed.

👉 Watch now, and join the conversation by leaving a comment or review.

Timestamps:

00:00 Opening and setup

00:42 Episode introduction

01:00 Workshops and unexpected contrasts

03:12 Ricky Williams and walking away from football

04:28 Cancer scans and living with uncertainty

05:20 Death as a daily presence

06:00 Prostate cancer diagnosis and treatment journey

10:43 Hormone therapy and energy loss

13:46 Feeling mortality in the body

14:16 Memento mori and midlife urgency

16:30 Legacy and ripple of impact

18:24 Near death experience story

22:47 Succession planning and leadership wisdom

23:18 Talking about death without fear

26:10 Purpose usefulness and meaning

28:20 Wisdom bumper sticker on mortality

30:04 Gratitude and closing reflections

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

#MidlifeWisdom #CancerJourney #LivingWithUrgency #MementoMori #MidlifePurpose #FacingMortality #LifeAfterCancer #ModernElder #MeaningfulLife #LegacyAndPurpose #MidlifeReflection #WisdomWednesday #PersonalGrowth #LifePerspective #ChipConley

In this candid and heartfelt conversation, Airbnb co-founder and CEO Brian Chesky joins Chip Conley to explore the hidden side of success. From imposter syndrome to the emotional aftermath of the IPO, Brian shares what midlife has taught him about ambition, belonging, and finally realizing he is enough. In this episode, you’ll hear:• Why success didn’t fix his loneliness• How leadership evolved from control to connection• The wake-up call that followed Airbnb’s $100B milestone• Why midlife is a chance to redefine what truly matters This is a conversation about growth, vulnerability, and choosing relationships over relentless achievement.If you’re navigating success, questioning your next chapter, or redefining what fulfillment means, this one’s for you.Listen in and reflect on what “enough” means in your life. Timestamps:00:00 Reunion and reflecting on 13 years since Airbnb began01:02 How Brian recruited Chip and the early Airbnb vision02:27 Chutzpah and learning from mentors04:00 Discovering hospitality as Airbnb’s true business06:43 Early partnership dynamics and mutual mentorship11:21 Advice to his 26 year old founder self12:20 Imposter syndrome and leadership growth15:42 From creative outsider to Fortune 500 CEO17:26 Childhood, not belonging and ambition22:48 Loneliness after success and the IPO realization27:54 Investing in friendships and rebuilding connection29:00 Founder mode and evolving leadership style37:24 Redefining success in midlife38:17 Hoffman process and realizing he is enough41:35 Fear of intimacy and unfinished business50:03 The Airbnb Open and scaling with soul54:20 Wisdom bumper stickers and life lessons56:04 In you lies unknown potential1:00:48 I am enough and always was Learn more about MEA at ⁠https://www.meawisdom.com/

Midlife isn’t a crisis. It’s an invitation to come alive again.

In this episode of Midlife Chrysalis, Chip Conley is joined by Susan Magsamen, a neuroscientist at Johns Hopkins, and Ivy Ross, Chief Design Officer at Google, for a warm, eye-opening conversation about why creativity is essential to being human, especially in midlife.

Drawing from their book Your Brain on Art, they share how art, play, and sensory experiences quietly support brain health, emotional balance, and a deeper sense of meaning in a world obsessed with productivity and speed.

You’ll hear why:

• Creativity is hard-wired into our biology, not reserved for “artists”
• Midlife is a powerful moment to rediscover curiosity, play, and making
• Small creative acts can reduce stress and help us feel more alive
• Art may be one of the healthiest counterweights to burnout and AI

The second half of life isn’t about doing more, it’s about sensing more, feeling more, and reconnecting with what truly matters.

👉 Watch now and let midlife become a chrysalis, not a cage.

Timestamps:

13:35 Guest backgrounds and journeys

18:36 What Your Brain on Art is really about

21:25 Neuroaesthetics and brain science

23:54 Why creativity is essential for health

24:24 How to rebuild creativity in midlife

29:14 Art, neuroplasticity, and medicine

34:32 Creativity inside Google

39:18 Digital literacy, nature, and balance

41:35 Personal midlife transformation stories

45:30 Resilience through illness and change

49:08 Life wisdom and defining moments

55:51 Final reflections and closing

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

#MidlifeChrysalis #YourBrainOnArt #CreativityAndAging #MidlifeWellbeing #Neuroaesthetics #BrainHealth #CreativityForAdults #MidlifeGrowth #ArtAndScience #HealthyAging #MentalHealthMidlife #PurposeInMidlife #CreativeLiving #SecondHalfOfLife #MidlifeInspiration

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/