The Midlife Chrysalis

What if the thing that makes you different has been there all along, you just haven’t named it yet?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore how to “excavate your essence” and uncover the unique gift that can guide your work, choices, and life.

You’ll discover:

• How Airbnb uncovered “Belong Anywhere” by looking beyond what the company does to why it matters
• A simple five-questi...

How do you find common ground with someone you profoundly disagree with?

At a time when political, religious, and cultural divisions seem deeper than ever, peacebuilder Shamil Idriss, CEO of Search for Common Ground, shares what decades of bringing people together have taught him about trust, conflict, and human connection.

In this conversation with Chip Conley, Shamil explores:

• Why being heard and respected matters more than bein...

Midlife isn't the beginning of the end. For more than 50 years, Dr. Ken Dychtwald, psychologist, bestselling author, and founder of Age Wave, has studied what it really means to grow older.

In this conversation, he explains why midlife isn't the beginning of the end, but the start of one of life's most meaningful transformations.

In this episode, you'll discover:

• Why midlife is a time of growth, not decline
• The powerful idea of "mi...

Don't wait until it's too late to tell someone what they mean to you.

In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?

In this episode, you'll learn:

• Why we struggle to expr...

Could one guided psychedelic experience transform the way you think, feel, and live?

In this episode of The Midlife Chrysalis, Chip Conley speaks with Neil Markey, CEO of Beckley Retreats, former Army Ranger captain, McKinsey consultant, and Harvard public health student, about the growing role of psilocybin in personal transformation and mental well-being.

Together, they explore:

• Why midlife may be the ideal time for a psychedeli...

We've been chasing happiness the wrong way. Dr. Laurie Santos explains what actually works.

Join Chip Conley and Dr. Laurie Santos, Yale's renowned happiness professor and creator of the university's most popular course, for a thought-provoking conversation on the science of happiness, the opportunities of midlife, and the habits that lead to a more fulfilling life.

In this episode, you'll discover:

• Why your brain often pushes you...

Do you ever feel like you're not good enough, even when you're succeeding?

You're not alone. In this Wisdom Wednesday, Chip Conley explores why imposter syndrome follows so many high achievers and, more importantly, how to break free from it.

In this conversation, you'll discover:

• Why imposter syndrome doesn't disappear with success
• How to replace fear with curiosity and become an "explorer" instead of an imposter
• Why vulnerability ...

In this eye opening conversation, bestselling author and aging activist Ashton Applewhite challenges everything we think we know about growing older. She reveals why many of our fears about aging come from culture, not reality, and explains how getting older can bring more freedom, confidence, and purpose.

In this episode, you'll learn:

• Why ageism is one of the last socially accepted forms of prejudice

• Why the conflict be...

What if your most meaningful chapter begins after 70?

Most people think aging is about slowing down. Dr. Philip Pizzo believes it's about discovering new purpose.

In this inspiring conversation, Chip Conley sits down with Dr. Philip Pizzo, former Dean of Stanford Medicine, founder of the Stanford Distinguished Careers Institute (DCI), physician, educator, and now a spiritual care provider, to explore how we can navigate life's bigges...

Don't wait until it's too late to tell someone what they mean to you.

In this inspiring Wisdom Wednesday episode, Chip Conley joins host Derek Gehl to share a powerful idea that could change the way we celebrate the people we love: the social eulogy. Instead of waiting until a funeral, why not tell people the impact they've had on your life while they're still here to hear it?

In this episode, you'll learn:

• Why we struggle to expr...

At an age when many people are slowing down, Pat Whitty walked 200 miles on Spain's Camino de Santiago — alone. But what started as a physical challenge became a profound journey of self-discovery, purpose, and spiritual renewal.

In this inspiring conversation, Chip Conley sits down with Pat to explore what happened when he stepped away from the noise of everyday life and spent 16 days walking with nothing but his thoughts.

In ...

Play isn't just for kids. It's one of the most powerful tools for navigating change, finding purpose, and becoming more fully yourself.

In this episode of Midlife Chrysalis, Chip Conley sits down with Kristine Michie founder of the Playful Podcast, and JD Schramm, communication expert and former Stanford professor, to explore how play, storytelling, and authenticity can transform the way we approach midlife.

What you'll discover:

• ...

Can AI really replace human wisdom? Or are we undervaluing the one thing machines will never have?

In this Wisdom Wednesday, Chip Conley and Derek Gehl explore a powerful idea inspired by the Spanish language: there are two different ways of "knowing." One is knowledge anyone, including AI, can access. The other comes only through lived experience.

In this conversation, you'll discover:

• Why AI can know facts but will never have re...

Midlife is far more hopeful and full of possibility than most of us have been led to believe.

In this episode of The Midlife Chrysalis, Chip Conley talks with Dr. Margie E. Lachman, one of the world's leading experts on lifespan psychology, director of the landmark MIDUS study, and author of Prime Time. Drawing on decades of research, she shares why midlife is one of the most important stages of life and how the choices we make toda...

Retirement isn't the end of your career. It's the beginning of the life you've been preparing for.

In this episode, filmmaker and former lawyer Stephen Herman and criminal justice reform leader Evelyn Neaman share the personal experiences that inspired them to rethink retirement and help others navigate this major life transition with purpose and confidence.

Together, they explore:

• Why so many people struggle after retirement, eve...

Have you ever wondered what your 80 year old self would tell you today?

In this episode, Derek and Chip talk about aging, relationships, purpose, and the life lessons that only become clear with time. Through a powerful exercise imagining a conversation with his future self, Chip shares the insights that have reshaped how he thinks about success, love, health, and what truly matters.

In this episode, you'll discover:

• Why talking t...

Burnout, career uncertainty, and midlife stuckness have become increasingly common, but stepping away may be the key to moving forward.

In this episode, Chip Conley sits down with DJ DiDonna, Harvard Business School senior lecturer, entrepreneur, and author of Big Time Off. After reaching burnout while running his dream company, DJ took a four-month sabbatical that transformed his perspective on work, success, and life.

In this conve...

Can your greatest purpose begin after 50?

In this powerful conversation, Chip Conley sits down with Lynne Twist, bestselling author of The Soul of Money, and her longtime collaborator Sara Vetter to explore purpose, money, mentorship, and the surprising opportunities that come with midlife.

In this episode, you'll learn:

• Why midlife can be the start of your most meaningful chapter.
• How a life-changing trip to the Amazon transformed...

Uncertainty is everywhere, from economic shifts and AI disruption to health challenges and major life transitions. The question isn't how to eliminate uncertainty, but how to navigate it with confidence.

In this Wisdom Wednesday episode, Chip Conley and Derek Gehl explore practical ways to stay grounded when life feels unpredictable. Drawing from his experiences as an entrepreneur and his ongoing cancer journey, Chip shares the tool...