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/

Cancer doesn’t just affect your health. It changes how you see yourself and your life.

In this warm and honest conversation, Chip Conley sits down with Caryn Lerman to explore the emotional side of cancer that often goes unspoken. Together, they talk about identity shifts, caregiving, and what it really means to move through the messy middle of midlife after a diagnosis.

In this episode, you’ll hear:

• How cancer reshapes identity, not just the body
• Why caregivers carry an invisible emotional load
• What it means to live intentionally after cancer
• How vulnerability can become a source of strength

Watch the full episode and join us for a thoughtful, compassionate conversation about healing, meaning, and becoming who you are now.

Timestamps:

04:14 Psychology of cancer survivors and caregivers

06:47 Identity loss and existential impact of cancer

07:53 Chip’s cancer diagnosis and early denial

13:13 Regret fear, and emotional processing

16:23 Cancer as a teacher and life priorities

19:39 Anxiety treatment and living with uncertainty

20:33 Staying busy to avoid difficult emotions

24:16 Values family and vulnerability

26:01 Strength identity and emotional suppression

28:01 Caregivers and lack of support systems

30:10 Invisible burden of caregiving

32:06 Emotional catharsis and healing journey

35:32 Caregiver and survivor archetypes

38:49 Inside the cancer thrivers workshop

42:18 Identity mapping and letting go

43:41 Meaning values and intentional living

45:42 How friends can best support someone with cancer

47:26 Cancer is not a linear journey

48:28 Wisdom bumper sticker advice

51:53 Growth outside the comfort zone

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

What if the way you start your morning is quietly shaping how your whole day feels?

Chip Conley sits down with Derek Gehl to explore why so many midlife routines start to feel empty and how turning them into simple, meaningful rituals can bring more calm, clarity, and purpose to everyday life. Together, Chip and Derek share:

• Why routines can feel mechanical, while rituals help us feel present and changed
• How to gently layer meaning onto things you already do, like showering or stretching
• Why small morning rituals can boost mood, energy, and emotional well-being
• How affirmations work best when they’re personal, specific, and emotionally real
• Easy ways to create micro-rituals that set a better tone for your day

If midlife has you longing for more intention without adding more to your plate, this episode is a friendly invitation to start small and start with your morning.

Give it a listen, try one simple ritual this week, and notice what begins to shift.

Timestamps:

02:12 Morning rituals vs routines

02:28 Routine vs ritual

04:00 Shower meditation prayers

05:48 Affirmations and new stretching ritual

11:21 The impact of morning rituals12:27 Accountability and consistency

14:01 Rituals as landmarks and micro rituals

15:24 How to create your own rituals

17:07 Science and specificity of affirmations

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

In this episode, Chip Conley sits down with Christine Sperber, co-founder of MEA and master experience designer, to explore how awe, ritual, and community can bring us back to life in midlife.

Drawing from ski town culture, life in Baja, and years of building transformational experiences, Christine offers a hopeful reframe of aging as something to design, not fix.

In this conversation, Chip and Christine explore:

• Why purpose matters more than productivity in midlife
• How simple rituals create meaning, resilience, and belonging
• What nature, movement, and community teach us about vitality
• Why transitions like perimenopause and loss call for compassion, not hustle

If midlife feels like a pause, a question mark, or an invitation to something more, this episode will leave you feeling seen, grounded, and hopeful.Listen now and rediscover what it means to feel fully alive in midlife.

Timestamps:

03:22 Christine Sperber’s background

06:55 Leaving Colorado for Baja

08:49 First experience of Baja and Pescadero

10:59 Freedom and living in rhythm with nature

15:15 Experience design and creating meaningful gatherings

17:48 Baking bread as ritual and collective practice

22:14 Origin story of MEA

24:02 Early doubts and building a local economy

26:07 Lessons from the first MEA beta cohorts

30:38 Ski towns, purpose, and longevity research

33:46 Aging, vitality, and midlife perspective

40:49 Introversion, ritual, and reclaiming time

46:19 Third vault conversations and authentic community

48:26 Moral beauty as a pathway to awe

54:11 Transformation through deep connection

56:19 Designing belonging and social bonds

57:28 Wisdom bumper sticker

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

Midlife isn’t the end of the story, it’s the chapter where something new wants to begin.In this episode of Midlife Chrysalis, Chip Conley sits down with Pam McLean, pioneering coach, co-founder of the Hudson Institute of Coaching, and a guiding voice on adult development and the “bonus years.”

Together, they explore why midlife isn’t about stepping back, but about letting go and moving forward with intention.

Pam shares:

• Why releasing old identities is essential for growth
• What the “bonus years” make possible at any age
• How Life Forward helps reframe change as opportunity
• Why discomfort, grief, and curiosity are part of becoming
• What truly makes a great coach — in life and in leadership

This is a warm, thoughtful conversation for anyone standing at a crossroads and wondering what comes next. Watch now and discover how midlife can become a powerful new beginning.

Timestamps:

03:32 Pam’s early life and background

04:17 From clinical psychology to coaching

07:06 How coaching has developed

09:31 Life Forward and Hudson Institute

11:46 The midlife happiness curve

14:53 Cancer as a life teacher16:06 Hudson Institute and MEA connection

18:08 Letting go of old identities

21:50 Navigating major life transitions

26:27 Why experimentation matters

27:39 Men vs women in midlife

31:01 What makes a great coach

33:47 Why people choose coaching

35:15 Gender balance in coaching35:51 Coaching in the age of AI

38:20 How to choose the right coach

40:38 Creativity later in life

42:41 Wisdom bumper sticker

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

Midlife isn’t falling apart. It’s asking for your attention.

In this episode of Midlife Chrysalis, Chip Conley dismantles the idea of the “midlife crisis” and replaces it with a far more hopeful and powerful framework: midlife as a chrysalis, a necessary transition into a second adulthood.

Drawing from social science, psychology, and his own deeply personal story, Chip explains why midlife often feels like a breakdown, why it’s actually normal, and how it can become the most meaningful chapter of your life.

In this conversation, you’ll discover:

- Why happiness dips in midlife and rises afterward

- How identity loss and burnout are signals, not failures

- Why midlife hits men and women differently

- How wisdom and purpose often peak later in life

If you’re feeling burned out, disoriented, or quietly wondering, “Is this all there is?”, the answer, as Chip shows, is no. This is where something new begins.

👉 Watch now to understand what midlife is really asking of you and how to move from breakdown to transformation.

Timestamps:

01:20 The Origin of the Midlife Crisis Idea

04:40 The U Curve of Happiness

06:21 Why Midlife Is Not a Crisis

09:12 Becoming a Modern Elder

11:24 Chip’s Midlife Struggles

21:11 Why Midlife Lacks Support Systems

23:17 Biology vs Life Circumstances

25:49 How to Move from Crisis to Chrysalis

30:23 Watching People Self-Destruct in Midlife

34:18 Rebranding Midlife for the Future

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

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