The Midlife Chrysalis

Many successful people reach midlife with a surprising question: What's next?

In this episode of Wisdom Wednesday, Chip Conley shares what he's learning from leading the Purpose Fellowship, a year-long program helping people redefine purpose beyond career, achievement, and old identities.

Chip explores why so many high achievers struggle to find meaning after success, how hidden patterns influence our choices, and why purpose is ofte...

He had the career, the success, and the recognition. So why was he miserable?

In this episode, Chip Conley sits down with leadership expert, bestselling author, and former Medtronic CEO Bill George to explore why success without purpose can leave even the most accomplished people feeling unfulfilled.

Drawing from personal loss, career setbacks, and decades of leadership experience, Bill shares the lessons that helped him discover his...

Most of us are far kinder to other people than we are to ourselves and according to leading self-compassion researcher Kristin Neff, that may be one of the biggest reasons we struggle with stress, burnout, anxiety, and self-doubt.

In this episode, Kristin shares how discovering self-compassion through Buddhism and mindfulness changed her life during a difficult period of divorce, uncertainty, and intense self-criticism. She explains...

Why does time seem to move faster every year?

One moment you're raising young children. The next, they're leaving home. So where does the time go?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore one of life's biggest mysteries: why time feels faster as we age and what we can do about it.

You'll discover:

• Why being a beginner makes life feel longer
• How flow states help us become fully present
• The surprising link between m...

Why do so many people feel overwhelmed, lonely, and unhappy in midlife?

Conley sits down with leading midlife researcher Frank Infurna to explore why so many middle-aged adults are struggling with stress, mental health challenges, and declining well-being, especially in the United States.

Drawing from years of research on aging and happiness, Frank explains why Americans report higher levels of loneliness and depression in midlife, w...

What happens when you do everything “right” in life… and still end up unhappy?

In this powerful conversation, I’m joined by Debjani Biswas, leadership coach, bestselling author, and TEDx speaker, to talk about burnout, reinvention, identity, and what it really means to live authentically. She shares her journey from turning down Harvard twice and breaking barriers as the only woman in her IIT engineering cla...

Are Millennials heading for a midlife crisis or redefining midlife altogether?

In this Wisdom Wednesday episode, Chip Conley joins Derek Gehl to explore how millennials are entering midlife differently than previous generations. After growing up through economic uncertainty, social change, and shifting life expectations, many millennials may be approaching midlife with a completely different mindset than their parents.

They discuss:

Many people reach midlife feeling successful on paper but disconnected from themselves.

In this conversation, Chip Conley talks with Carolyn Buck Luce about what it actually looks like to rebuild your life in your 40s, 50s, 60s, and beyond. Carolyn opens up about leaving Wall Street, going through a very public personal crisis, redefining ambition, and creating the “Decade Game”, a simple but powerful way to think about ...

For nearly 90 years, researchers tracked one question: what actually makes people happy, healthy, and fulfilled as they grow older?

In this episode, Chip sits down with psychiatrist, Zen teacher, and Harvard study director Robert Waldinger to explore what 88 years of research can teach us about relationships, aging, purpose, and emotional well-being.

Together, they unpack:

• Why strong relationships predict happiness and longevity b...

Anxiety, burnout, and emotional overwhelm make a lot more sense once people understand what’s actually driving them.

In this episode, Chip Conley, founder of MEA, former Airbnb executive, and bestselling author of Emotional Equations, talks with Derek Gehl about the hidden patterns behind anxiety, fear, purpose, and emotional resilience.

Chip shares powerful insights on:

• Why anxiety comes from uncertainty and powerlessness
• Th...

The parts of ourselves we silence are often the very things that make us come alive.

In this heartfelt episode of Midlife Chrysalis, I sit down with Gail Larsen, transformational speaking teacher, author, and longtime MEA faculty member, for a soulful conversation about authenticity, creativity, aging, and finding your voice.

From growing up in a restrictive religious environment to helping thousands of people discover their “o...

You hit your biggest goals… and still feel empty?

In this episode, performance expert and bestselling author Brad Stulberg breaks down why success alone doesn’t fulfill us and what actually does.

Drawing from his own experience with burnout, mental health struggles, and years of research, Brad shares a powerful new way to think about excellence, purpose, and what it really means to live well.

Here are a few key takeaways:

Why So Many Successful People Struggle With Retirement What Comes After Ambition but Before Retirement?

The Hidden Midlife Crisis Between Success and Retirement 

What happens when you stop chasing success… but you’re not ready to retire? 

In this episode of Midlife Chrysalis, Chip Conley and Derek Gehl explore a stage of life many people experience but rarely talk about: feeling caught between ambition and retir...

What do you do when the version of yourself you built for decades no longer fits your life?

In this conversation, Chip sits down with therapist and former theater director Ben Yalom for a warm, honest discussion about reinvention, grief, aging, identity, and the courage it takes to change direction in midlife.

After spending years in experimental theater, Ben found himself at a crossroads during COVID. What followed was an unexpected...

In this episode, I sit down with gerontologist Kerry Burnight, who has spent decades working with people in their 80s, 90s, and even 100s. And what she’s learned might completely change how you think about aging, and how you choose to live right now.

Kerry introduces a powerful idea called joyspan, the missing piece between how long you live and how well you live. And the truth is, most people are getting this wrong.

Here are a...

What happens when life changes all at once?

In this deeply emotional conversation, Chip opens up about one of the hardest seasons of his life: facing stage 3 cancer again while grieving the loss of his mother, navigating relationship changes, caring for his aging father, and trying to hold onto purpose through it all.

But this episode isn’t about giving up. It’s about what keeps us going when life feels unbearably heavy.

Y...

The moment everything starts falling apart might be the moment your life finally comes together.

In this episode, Chip Conley sits down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change.

Here’s what you...

What if the life you built… no longer feels like yours?

In this powerful episode, Kelly Wendorf joins Chip Conley for a raw conversation about loss, identity, and the moment everything shifts. From caring for a dying parent to rediscovering yourself through nature, this episode goes straight to the heart of what it means to truly live.

Here’s what you’ll take away:

• Why success can still leave you feeling empty
• Ho...

AI is changing work faster than anyone expected… but most people are focusing on the wrong thing.

In this episode, Chip Conley and Derek Gehl break down what AI actually means for your career, especially if you're in midlife and wondering where you fit in.

Here’s what matters:

• AI is replacing routine work first, not higher-level thinking
• Wisdom now matters more than knowledge in an AI-driven world
• Over-relying on AI can...