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Why Birthdays Matter More as We Get Older

The Midlife Chrysalis

September 16, 2026

Why do we celebrate birthdays as kids, then slowly stop celebrating ourselves as we get older? In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl for a conversation about birthdays, aging, and why life’s milestones deserve more attention, not less.

Speakers Chip Conley, Derek Gehl

TopicsSelf-ImprovementEducation

Chip Conley (0:00)

What I'll just say, as somebody who has had to deal with the prospect of death, twice, once due to an NDE, a near-death experience, with an allergic reaction to an antibiotic at age 47, and then more recently with my cancer, why not celebrate life? I don't want my ultimate celebration to be my funeral because I won't be there.

In a living form, at least.

Derek Gehl (0:22)

Yeah, yeah.

SPEAKER_3 (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.

Derek Gehl (0:41)

Welcome to another episode of the Midlife Chrysalis podcast, the Wisdom Wednesday edition. My name is Derek Gehl. I'm the CEO here at MEA, and I'm with our founder, Chip Conley. Chip, hello.

Chip Conley (0:53)

Hey, Derek. How are you doing?

Derek Gehl (0:54)

I'm doing well. I'm doing well. Here we are.

We're mid-September, heading for fall. Heading for fall.

Chip Conley (1:00)

Heading for my birthday.

Derek Gehl (1:02)

Heading for your birthday. In fact, that's what we're going to talk about today.

You wrote a line recently. I forget where I read it. Kind of stuck with me, and that was that you almost didn't happen.

Chip Conley (1:15)

That's true for all of us. It really is.

Derek Gehl (1:17)

When you think about it, when you think about what had to occur, the odds of you being here is pretty. Yeah.

Chip Conley (1:26)

Pretty slim.

Derek Gehl (1:27)

Why do you think that lands differently now in midlife and later life than it did earlier in life?

Chip Conley (1:34)

I mean, I think, you know, when you're a kid, you don't even really understand how you came into this world with your parents. And over time, you learn the birds and the bees, and then you get sick to the thought, like, oh, my God, my parents did that.

Like, oh, that's a really awful visual. And then you start doing those things yourself, and then you realize, oh, my gosh, those things will lead to children in the case of a heterosexual relationship. And long story short is, you know, at some point you start to see the linkage of it all. But I think, you know, for me, I have been celebrating my birthday. I feel like I've known for a long time that we under ritualize our lives. And when I was 30, I decided to do a birthday party for myself. And I invited and had about 30 friends on the island of Kauai. And we got a bunch of houses on this sort of, this beautiful bay, Anahoua Bay. And we had a wonderful five days together. And I was like, that was fun. Like I like the idea of celebrating life. And so 35, I like up the ante and we went to Bali. And this time it was about 24 of us. But 24 people all going to Bali together.

For my 30th birthday, I was like, wow, that was a big deal.

And I fell in love with Bali. Bali became my favorite place in the world as a result of that celebration. And then 40, we did the Mandalay Bay in Las Vegas. This was, so it was, I was recently single. Orin and I, after 11 years split up before we came back together 16 years later. And so like you're single and you want to go party. It's like, we're going to Vegas. And this was a long time ago. This was 26 years ago. So Vegas was starting to like become cool and hip. And the Mandalay Bay had the House of Blues on the top floor. And we were going to do the gospel brunch. And oh no, that was on the ground floor. And then on the top floor, there's the Foundation Room, which is like a VIP private place. And I got the ability to have my birthday party there. So yeah, that was interesting. 45 was Marrakesh, Morocco. I mean, I know this is sounding a little bit bougie to all of you. I'm not saying this to show off. I'm sort of saying this to say the history. 45 was Marrakesh, Morocco. And I loved it because Marrakesh is one of those places that the Arabic, the French, English, it's a fascinating sort of bouillabaisse of a culture. 50 was Burning Man.

We had 120 of us in Maslow-Topia.

Maslow-Topia is like a self-actualized community.

Fifty-five was Toto Santos, which was in Baja before I had decided to buy a house there and ultimately create MEA. And then 60 was supposed to be Esalen, taking over all of Esalen, throwing a workshop, public workshop, but with all my friends knowing about it. And then COVID, and so didn't have a 60th. And then three years later, my prostate cancer went from one, stage one to two to three. So I decided to throw a 64th birthday party, not knowing, like, okay, I don't know how many years I have left now. I did throw a 64th birthday party at the ranch here. And that was with, but it was just a private thing with a handful of friends. Actually, it's probably a lot of friends, but.

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