The Midlife Chrysalis

Surfing at 87, Writing at 91: James Flaherty’s Rules for Life

At 91, James Flaherty isn’t slowing down. He’s still writing, creating, learning, and planning what comes next. A former advertising executive, entrepreneur, innkeeper,

From Role to Soul: Who Are You Without What You Do? | Connie Zweig

Aging isn’t just about getting older. It’s about discovering who you are when the roles that once defined you begin to fall away. In this episode, Chip Conley sits down

You Can’t Rush Grief: Learning to Feel What We’ve Lost

Some losses hit harder than we ever expect, and grief doesn’t follow our timeline. In this deeply personal episode of Midlife Chrysalis, Chip Conley opens up about the u

What Happens After You Achieve Your Biggest Dream? | Paul Harris

What happens when the identity you've spent your entire life building suddenly disappears? Former South African international cricketer Paul Harris reached the highest l

From Doing to Being: The Power of Presence | Teddi Dean

Sometimes the most powerful thing we can do is stop doing and simply be present. In this episode, Chip Conley talks with Teddi Dean, former Bones Brigade skateboarder tu

Curiosity Is the Secret to a Richer Life

Happiness and purpose may not be enough for a truly rich life. In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness a

We’re Living Longer. Why Isn’t Society Ready? | David Sinclair

The longevity revolution isn’t coming. We’re already living it, and we’re not ready. In this episode, David Sinclair of the International Longevity Centre joins Chip Con

From Achievement to Fulfillment: Building Your Life 3.0 | Seth Streeter

Success can look impressive on the outside and still leave you feeling like something is missing.Seth Streeter, co-founder of Mission Wealth, spent decades building a suc

Could Living Together Be the Secret to Aging Better?

Growing older is changing. Maybe the way we live should change with it. In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to la

You Got Everything You Wanted. Now What? | Edward Sullivan

What happens when you achieve the success you've worked for... and it still doesn't feel like enough? In this episode of The Midlife Chrysalis, Chip Conley sits down wit

Follow the Energy, Not the Career Script | Arun Gupta

Your job title tells people what you do. The problem you care about tells them who you are. Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins

How to Discover the Gift That’s Uniquely Yours?

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 “

How to Talk to People You Profoundly Disagree With | Shamil Idriss

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

Why Retirement Is the Wrong Goal | Ken Dychtwald

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 m

Why Midlife Feels Stuck (And How to Break Free)

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 i

How Psilocybin Can Change Your Life After 40 | Neil Markey

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 o

Your Brain Is Lying to You About Happiness | Dr. Laurie Santos

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 a

Why High Achievers Still Feel Like Imposters

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

The Biggest Lies We've Been Told About Aging | Ashton Applewhite

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

Why Your 70s Can Be Your Most Meaningful Years | Dr. Philip Pizzo

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 th