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What If the Life You Built Isn’t the Life You Want? artwork

What If the Life You Built Isn’t the Life You Want?

The Midlife Chrysalis

October 7, 2026

You’ve built a life that looks successful. Yet the things you worked so hard for may no longer be what you want next. In this Wisdom Wednesday episode, MEA founder Chip Conley joins Derek Gehl to explore finding purpose when familiar roles no longer feel fulfilling.

Speakers Chip Conley, Derek Gehl

TopicsSelf-ImprovementEducation

Chip Conley (0:00)

So purpose driven is this idea of 10 years from now, what will you regret if you don't do it now? For me, having just spent the weekend with my sons in Houston, who are 14 and 11, knowing that I don't get to do adolescence over again with them, means that I am prioritizing something that doesn't necessarily come naturally to me.

SPEAKER_2 (0:19)

This is The Midlife Chrysalis.

Welcome to Wisdom Wednesdays with Chip Conley and Derek Gehl. Your weekly conversation about thriving in midlife. Together, we explore the questions, insights and practices that help you live this chapter with more purpose, vitality and joy.

Derek Gehl (0:36)

Welcome to Wisdom Wednesday here at The Midlife Chrysalis podcast. My name is Derek Gehl, CEO here at MEA and I'm with our founder, Chip Conley. Chip, how are you? Good. All right. We're going to talk about purpose today.

SPEAKER_2 (0:48)

Yeah.

Derek Gehl (0:48)

You've been immersed in purpose for the last year. Actually, let's frame this.

Just over a year ago.

SPEAKER_2 (0:57)

Yeah.

Derek Gehl (0:57)

Just over a year ago, you're like, hey, let's do a purpose fellowship.

I mean, we've been doing cultivating purpose, which has been one of our core workshops now for. When did that one start?

Chip Conley (1:07)

Pretty much just after COVID. I think when we started actually having it as a separate workshop. Yeah. It's a topic that people talk about all the time, but in the US culture, it's almost as if it's a possession. We think of purpose as a noun, not an adjective. I like to say you can't get the noun unless you do the verb. The verb is being purposeful and not think of like, oh, everybody has a purpose but me as if it's a BMW in the driveway. Yeah. No, purpose is an action.

Some of the myths around purpose are that there's the singular purpose myth, which is the idea that you only have one purpose in life. Yeah. No, purposes can change. As you get older, you have a purpose portfolio. You have some big P purposes and some small P purposes.

You have a collection of purposes all together. I think more than anything, there's just this sense that purpose is, because there's a lot of different ways to get to purpose. Maybe we can talk about that in terms of my four pathways that I like.

Derek Gehl (2:08)

Well, okay. Why midlife? I even recognize this now.

I never thought about purpose in my 20s or my 30s, and now as I'm staring down 50 months away, that's why I'm here.

Chip Conley (2:22)

I'm like, you could make more money elsewhere.

Derek Gehl (2:27)

But it's about having purpose. Why do you think midlife is such a time that this becomes a thing?

Chip Conley (2:32)

I think there's four reasons. I think one is there's something called the success script, and it is often what was handed to us, not necessarily consciously by our parents or our community. It's the definition of success that we inherited. And for a lot of people, as they hit midlife, they're looking at their definition of success and starting to think like, that's someone else's. I've been reading the script from someone else's screenplay. And so then the question becomes like, well, if it's not this success script, what is my own success script? And purpose is woven in with that. And so the idea of having a purpose is there's something about that it's an alternative way of looking at success. But here's the bigger thing. As you get to midlife, you start to realize, okay, I only have half of my life ahead of me, or half of my adult life ahead of me. How do I want to use that time? And you get a little bit more judicious or discerning about what matters to you. And therefore, maybe making a ton of money is less important, or maybe having your name in the lights is less important, or working for a company that has stature and has reputation is less important to you. And that's why, frankly, the number of people after age 50 who decide to start their own business is huge partly because people are like, you know what?

I don't want to have to do it the way I have to answer to the boss. Yeah. So purpose is important. The problem is we don't have very good methods for helping people to find it. Sometimes we say, go find your passion. But your passion isn't necessarily your purpose. Your passion could be your purpose. This idea of the Ikigai, I-K-I-G-A-I, the Japanese point of view on purpose says that the purpose is the bullseye in the middle of four circles of a Venn diagram. What you love doing, what you do well, what you get rewarded or paid for, and what the world needs.

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