Stop Trying to Fit In: The Hidden Gift of Aging artwork

Stop Trying to Fit In: The Hidden Gift of Aging

The Midlife Chrysalis

July 1, 2026

What if one of the greatest gifts of aging is finally caring less about fitting in? In this Wisdom Wednesday conversation, Chip Conley and Derek Gehl explore why growing older isn't just about gaining wisdom, but about gaining the freedom to become more fully yourself.
Speakers: Chip Conley, Derek Gehl
**Chip Conley** (0:00)
I think the thing that's beautiful as you get older is I want to be admired, but I want to be admired for who I am as I am, and I want to integrate. So as we grow old, we grow whole. So what does that mean? It means you actually learn how to be less compartmentalized. One of the beauties of getting older is not just getting weirder, but it's getting whole and being integrated into all of the different parts of yourself.

**Derek Gehl** (0:24)
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.

**Chip Conley** (0:41)
Hey Derek.

**Derek Gehl** (0:43)
Chip.

**Chip Conley** (0:44)
Hi. How many provinces does Canada have?

**Derek Gehl** (0:49)
Well, since it's Canada Day and you called me out on that before we first got started. We have 10 and three territories.

**Chip Conley** (1:00)
Oh my gosh. Where are the territories? What are they?

**Derek Gehl** (1:02)
Territories. We're up way up north. You got the Yukon territories, you got the Northwest territories, and then you've got none of it.

**Chip Conley** (1:11)
None of it? There's a place called none of it? I thought it was called Newfoundland.

**Derek Gehl** (1:15)
Oh, there's Newfoundland as well. Yeah.

**Chip Conley** (1:17)
Wait, none of it?

**Derek Gehl** (1:18)
Yeah, none of it. It's up on the-

**Chip Conley** (1:22)
Wait, there is a place called none of it Canada?

**Derek Gehl** (1:25)
Yeah.

**Chip Conley** (1:26)
I want none of it.
You can have all of it. We're doing this different today. This is Wisdom Well. This is Derek Gehl, our CEO, and I am the founder, executive chair of MEA, and we had these conversations every Wednesday on the Midlife Chrysalis Podcast. What are we going to talk about today? Weird.

**Derek Gehl** (1:46)
Well, we're going to talk about weird and it seems fitting the way we started this one. That's right.

**Chip Conley** (1:51)
Exactly. That's why I did that.

**Derek Gehl** (1:52)
Okay. So you wrote that a recent New York Times piece confirmed the way you had already suspected and that-

**Chip Conley** (1:58)
Well, not suspected. I amplify. I exhibit.

**Derek Gehl** (2:02)
Yes. Yes. Yes, you're exhibiting.
Less about, it's less about becoming elderly and more about becoming delightfully unhinged.

**Chip Conley** (2:12)
And weird.

**Derek Gehl** (2:12)
We'll talk about that. What the heck does that even mean?

**Chip Conley** (2:16)
So delightfully unhinged just means that you're sort of like, again, if it was just unhinged, that could be problematic.

**Derek Gehl** (2:22)
Delightfully unhinged.

**Chip Conley** (2:23)
Delightfully unhinged basically means you are not living by convention. You are operating in your own realm in a way that's slightly eccentric. Don't you love old ladies who have blue hair and fashion and like, you know, Iris, I think she's died now, Iris Apple, and she's like kind of this big glasses and we just love that.
Eccentric older people. I mean, and the idea of being weird. Back in the day, Michael Mead, the famous mythologist has written about this, the word weird in going back to folkloric times was spelled W-Y-R-D and it often did mean an elder. It meant an elder who had moved beyond social convention. And so what's interesting is when someone gets to a place in their life that they have no more Fs left to give.
And they are just a true original. And I think that's what many of us aspire to. How do you break with the convention that has in some ways been very limiting? There's a, as you and I both know, Robin from one of our MEA alum. Raffer? Raffer, Arthur Raffer, a Fisher Raffer.
She says, you know, midlife is about freedom finally. And it's like freedom to fly your freak flag.
And that doesn't mean that you're dysfunctional. That doesn't mean that you're not thoughtful and caring. It just means that you no longer are trying to people please. When I wrote the book Wisdom at Work, The Making of a Modern Elder, one of the five qualities that I highlighted in the book based upon some social science data around who is a modern elder in life, is that somebody who has unvarnished insight. So that's another form of weird. Unvarnished insight means you just say it like it is, and you have a way of seeing the world that's a little bit different, so that you can help people to see things that they wouldn't see on their own.

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