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 Ghal 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/