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

James Flaherty (0:00)

You have accumulated wisdom. You have answers to questions that perhaps you've never asked yourselves.

As I said to a friend of mine the other day who's having some serious problems with himself, with some depression, I said, you must get well because there are people out there who need you, people you don't even know who need you. You know, our wonderful Pico asked us, what is your source of strength? I said, it's the wisdom and love and needs of other people and how I respond to that. Welcome to The Midlife Chrysalis Podcast with Chip Conley, where we explore how midlife isn't a crisis, but a Chrysalis, a time of profound transformation that can lead to the most meaningful chapter of your life.

Chip Conley (0:51)

Welcome to The Midlife Chrysalis. This is Chip Conley and you know, I love my dad.

My dad is 89 years old. And if I had an alternative dad, it would be this guy. Jim Flaherty is sort of the father of MEA, in the sense that he's been to seven workshops.

He first came to a workshop when he was 87 years old. But more than anything, he's just full of wisdom. But not the kind of wisdom that you just sort of dispense with a robe and a white beard, but more like lived wisdom and funny wisdom. He's got a sense of humor. He's a bit sassy. And you're going to hear today a little bit about how to live a good life into your 90s and beyond. I think you're going to enjoy it. He says things like courtesy is contagious.

What is it like when you walk into a room? How do people respond to that? He was a creative director and a madman back when madmen were doing all the crazy stuff they were doing on Madison Avenue. I think you're going to enjoy this one because you're going to be inspired by Jim Flaherty. So at the end of the episode, I'll tell you my three key lessons from this episode. Mr. Jim Flaherty. Oh my gosh. Here you are on The Midlife Chrysalis, a 91-year-old. We have just expanded the definition of midlife in a substantive kind of way.

James Flaherty (2:14)

That's right.

Chip Conley (2:15)

So tell us. Okay. So you've gone to seven MEA workshops and you're here for the Pico IR workshop right now. And let's talk a little bit about what brought you to MEA in the first place. And then I want to go way back because 91 years a long time ago.

James Flaherty (2:34)

Okay.

Chip Conley (2:35)

But what brought you to MEA?

James Flaherty (2:36)

I read Wisdom Well for two years.

Chip Conley (2:39)

That's my daily blog.

James Flaherty (2:40)

A friend of mine, a late friend of mine told me, you've got to read this, Jim. I know you would love it. I read it for two years and I thought I've got to know this person. So I booked the first one. I always said it was one of the most magical workshops in the world. It was you and Dan Buettner together.

Chip Conley (3:01)

From Blue Zones.

James Flaherty (3:02)

From Blue Zones. You all had advertised it as longevity with the Blue Zones. It wasn't Blue Zones and longevity.

Because not many people in the world knew Blue Zones at that point. Yeah. It was about four years ago.

Chip Conley (3:20)

This was before the Netflix special. Yeah. Oh yeah.

James Flaherty (3:23)

And it was a magical week.

Chip Conley (3:27)

You and Dan got along famously.

James Flaherty (3:30)

We stayed friends.

Chip Conley (3:32)

And his girlfriend, long time girlfriend off and on. Stephanie. Oh, she's darling. Yeah.

James Flaherty (3:38)

Yeah.

Chip Conley (3:39)

And you were just, you were a peach. You were so much fun to hang out with. You were 86 or 87 at the time.

James Flaherty (3:45)

Yeah.

Chip Conley (3:46)

87 You actually went surfing.

James Flaherty (3:50)

Yes. I said, fine, I'll do it. But then I never have to do it again. Yeah. You held on to the board.

Chip Conley (3:55)

We have photos of it. What was it like? Well, you know, and what is it like in almost every room now, except for one time when you came to a workshop and you were not the oldest, I don't think.

There was Dorothy. Wasn't she, were you in a workshop with someone who's older than you yet or no?

James Flaherty (4:11)

I, not that I know.

Chip Conley (4:12)

No. Okay.

James Flaherty (4:13)

All right.

Chip Conley (4:14)

So what's it like to always be the oldest person in the room?