Chip Conley on Finding Contentment and Embracing Our Achievements

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2:07Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors.

2:57Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I have a weird habit. Maybe you picked this up about me. Maybe you haven't. Maybe you noticed it from the podcast, but I have a lot of really old friends, like a lot of really old friends. George Raveling is in his late 80s, is someone I talk to on a very regular basis. You might have noticed a guy named Judge Frederick Block, who blurbed The Obstacle is the Way, who I've known now for 10 years. He was in his 80s when I met him. He is much older now. And that's just a collection of some of the people that have mentored and influenced and inspired me over the years.

3:36I didn't know, like I didn't have a term for what they were in my life until I met today's guest. Chip Conley calls them elders. Specifically, he calls them modern elders, right? Like people who, and that's the role that Chip Conley played at Airbnb. He was a successful hotel entrepreneur and he met the founders of Airbnb and they brought him in. He didn't have like a set job description, but he was just there to kind of be a good influence, to help them with problems that he'd faced in his life, to have good energy, to be an advisor, a thinker, to help them see big picture, to help them. You know, he'd been through the kinds of things that they were going through.

4:15It was a great partnership. And I met Chip Conley at an event where another sort of elder in my life was there, also been on the podcast, Kevin Kelly. We were at Powder Mountain in Utah. It was a summit event that I was speaking at. And we sort of became friends. We've chatted back and forth over the years. And he has this new book coming out. He's moved to Austin. And I said, you got to come out and do the podcast. and we had an awesome conversation. This is a dude who knows business, but more importantly, he knows life. He has an MBA and a BA from Stanford, an honorary PhD from Saybrook University.

4:56He's been a TED speaker and he's written seven books, multi New York Times bestselling author. His latest, Learning to Love Midlife, 12 Reasons Why Life Gets Better With Age. And I guess I am approaching mid age. That's a scary thought. I still see myself as the young kid. But this was a great conversation. We talked about journaling. We talked about ego. We talked about elders. We talked about influences. We talked about time. Talked a lot about the Stoics. He was just a great dude, a great influence. I'm so glad he came out. You can follow him on Instagram and Twitter at Chip Conley. You can check out his new book, Learning to Love Midlife, 12 Reasons Why Life Gets Better with Age.

5:40And do check out his book on modern elders. Check out his Modern Elder Academy also, which is the world's first midlife wisdom school with regenerative communities. He's disrupting higher education and senior living and just overall great and super nice guy. I think you're really gonna like this interview. Thanks to Chip for coming out. Enjoy.

6:14We have a, there's a property that we have in Santa Fe, two different ones, but one of them is a former Catholic retreat center and seminary. Yeah. And it's got a chapel in it. Yeah. And so we're turning it into this enormous library, two stories, sort of like, you know, like Harry Potter. Sure. 100 ,000 books. Wow. Yeah. Where are you getting 100 ,000 books? Oh, that's, well, thank God we have a lot of alumni. We have 4 ,000 alumni. And so people are giving us their collections. Interesting. Yeah. A lot of these, like in the book tower and in the thing, there's this company called Books by the Foot.

6:48Oh. And they sell, they do a lot of stuff for like film studios. Oh, I've heard about them. Or whatever. But it's basically, and you can be like, I only want green cloth bound books. Or you can be like, I. And it's really affordable. Yeah. Because they're just doing it by scale, you know. And so you literally are buying by the foot or the pallet or whatever. But you're saying I need, I have 28 feet of shelf space that I need filled and I want only leather bound antique books. Or you're like, I'll take literally anything. And so like when we did this, like a lot of it was like, you know, with drugs, like they cut them.

7:26Yeah, yeah, yeah. A lot of them are cut with like cookbooks or like things that are big, but no one would read. So you kind of. Encyclopedia Britannica. Exactly. there's just like or different trends like you could probably get hundreds of feet of just 50 shades of gray or romance novels or vampire books but anyways yeah it's a it's a it's it's always cool when people find like weird niches that they can build like big businesses out not big but like oh that's a need that people have for stuff you know right like like for the tower it's like no one can see the books that are 20 feet up so no no but i still need it aesthetically to be filled you were meant to be a boutique hotel designer yeah i bet i bet hotels are a bunch oh my gosh hotels boutique especially boutique hotels are very much about the how what does it feel like not so much what does it look like what does it feel like and the feeling has look involved in it but it's like the scent actually one of the things we used to do back in my day when i had 52 boutique hotels was like we had a five cent test and so within the first five minutes you had to come into the hotel and feel like how are your five senses stimulated in a way that fits the five adjectives that define the hotel so each hotel had a magazine that defined the hotel and five adjectives sure and so you each hotel had to have a different approach to and you might not actually the the majority of guests are never going to open the magazine but as they pass by the coffee table what is it evoking for them?

9:04They're just seeing it is the thing. Not only they're not seeing it, but they're seeing it, but they're also feeling what we call the identity refreshment. So you are where you sleep. The place you're staying in, if there are aspirational adjectives that define the place, and by being there, you actually, it rubs off on you. But the reason I got the idea is, have you ever been to Ford's Theater in Washington, D.C.? Yeah, yeah. You go to the theater and then there's a museum next to it and they have like this spiral column that goes from floor to ceiling made up of books about lincoln yeah and i was like that is the coolest thing i've ever seen and i wanted to do like when we were designing the bookstore one of the things i was thinking of is like um this feels like a little marketing but it makes sense to me which is like what is the thing that you're taking pictures of yeah in front of while you're there yeah you've already made the You've already made the trip, but then how are you documenting or sharing that experience?

10:02There needed to be some sort of central focal point. And the more aesthetically pleasing and interesting that was, the more photos there would be, etc. And so that's why we built that book tower. And if you started to take them out? These are all, so in there, a lot of them are glued and screwed in. okay got it um actually this this this kid he was like my neighbor where we live out in the country yeah he um he he came over to my house when he was like 16 and asked if he could like do handyman jobs and he's become this very skilled craftsman as a result i sort of sketched out what i wanted and he figured out he's probably 19 at the time he figured that out and then so by the time he did it in here he'd perfected the system a little bit um on the on the on the fireplace the big issue was the weight yeah because it's a these are both old buildings but once you're 20 feet tall of something of hundreds of things they started to get so a lot of those books are cut like the book is sideways he's cut here so it's actually not the full book just got it just to just to Eliminate a lot of weight.

11:14Yeah, half the weight. Yeah, and then we were also thinking you could drill through, like, you know, like a big drill bit. You could just cut out the center or something. But here it wasn't as important because this is only like 10 feet or whatever. But they don't come out. They're all screwed in there. That's a lot of work. Or glued. Yeah, it's like. But it's just, you know, I mean, the only thing that's missing is that wall and over here. Actually, I loved at some point when I have more time in town, I'd love to have you come to my place at 70 Rainey because my library my office is a library and it is all three of the four sides have books so yeah the only reason I didn't do it over there is so this wall was already covered when we put this in so this was a barber shop the other one was like a harness shop this was the one we did most recently but that brick wall it had plaster on it but it there wasn't anything built in front of it yeah i felt i don't know about you but i felt weird covering up exposed brick yeah and that it's so nice no i didn't want it so we didn't we didn't go all the way around for only for that reason okay all right well we are floors too we are both sort of into our book so of course uh what a surprise um and these are only books that i don't care about in the sense that i would never do this to a book that i actually cared about Oh, really?

12:39Yeah. So these are not books that you... Well, I wouldn't ruin hundreds of my books. I understand, but these are books that you like still, right? Well, a lot of them are from Books by the Foot. And then what's mixed in here are books from friends of mine. I have my publisher send me a copy of every book they publish. I mean, some of these books you have multiple copies of. So that's true too. Yes. Although actually, I do remember when we were unloading them from the truck, they had to stop me because I would see books. I was like, oh, I want to read that. I was taking books out of the thing, which I subsequently read.

13:10But yeah, this is it. Well, welcome. Thank you. I thought we would start your term, a modern elder. Let's start with the definition there. Yep. What does it mean? And we're rolling. We were already rolling. Okay, good. So the origin of the term modern elder came from when I was at Airbnb. So I was a boutique hotelier for 24 years. Started Juad de Vivre, became the second largest boutique hotelier in the U.S. 52 hotels around California. And then I had what it's commonly called a midlife crisis in my 45 to 50 period. We'll come back to that. And then I ended up at Airbnb. And within the first, and I was 52 at the time, and the average agent in the company was 26.

13:53The founders asked me to come in and be their in-house mentor. And about - So they saw the role as that specific. It wasn't like, hey, we're going to hire you because you're an expert. And then - No, that's exactly what happened. but they hired me for my knowledge. You know about hospitality, you know about entrepreneurship, you know about leadership. But about a month or two into it, they said, we hired you for your knowledge, but what we've really gotten is your wisdom. You are our modern elder. And I said, I don't want to be your modern elder. You're making fun of my age. But then they said, a modern elder is someone who's as curious as they are wise.

14:27And when I heard that, the alchemy of curiosity and wisdom, I realized, wow, that's what I aspire to be. I would love to be a modern elder. And yeah, guess what? I was twice the age of the average person there. And the founders were between 29 and 31. And I was 52. So bottom line is I said, like, okay, I'll own it. And so then I needed to become a mentor, a mentor and an intern at the same time. Because I never worked in a tech company before. And so I had to learn. It's probably been a while since you had a job. Yeah. Well, it's definitely been a long time since I had a boss as well. So I was mentoring Brian Chesky, the CEO and co-founder, while he was my boss.

15:09Sure. I was the head of global hospitality and strategy. So what's it like to have your mentee be your boss? Right. So we built a really beautiful symbiotic relationship. And so that's how the Modern Elder idea came about, was there four years full-time and then three and a half years part-time as a strategic advisor taking them up to the IPO. Yeah, so what is modern adding to the idea of an elder? Like obviously historically and traditionally there's been elders in a community, in a church, in a country. There's sort of been that elder role. What do you feel like modern is modifying? Well, I think there's a couple things.

15:53Number one is modern is modifying the idea that you're not just a wisdom dispenser, you're a wisdom seeker. Oh, okay. And so it's not just about being the wise one, but you're the curious one as well. Not to say that elders have always had some curiosity attached to them, especially Stoics. But a lot of it to me comes down to this idea that it's not about reverence, it's about relevance. Yeah. And reverence is what we have historically spoken about, especially in American culture. You have revere your elders. That idea has sort of fallen by the wayside. And that's a whole other story we can talk about if you want.

16:33But the idea that you're not, you didn't earn the idea of being an elder by just getting older. Sure. You had to be not just revered, but you had to be relevant. And being relevant required you to be curious. So in modern, is it just, oh, I had this wisdom from a long time ago, but that I also know what's happening now. And how do you put it in the context? Yeah, sure. So for me, like if I'd gone to Airbnb and I'd been a traditional elder, I would have just taken my knowledge of the hospitality of the hotel business and say, well, it takes a maid, you know, in an eight-hour day, a maid can clean 14 rooms.

17:13Yeah. Like that wasn't very, very relevant. Sure. And within the context of Airbnb. So if I was sort of the old school, I don't even want to call it an elder, but just the old school hotel, hotelier, I would have come in and just said, like, here's how you do things. But I actually had to sort of say, okay, I'm curious. I'm going to start by actually being the intern. How do I learn about what the context is and then see how my wisdom might fit in there? and that requires a certain amount of humility which was not something I when I was a 24 year long CEO of my own company I didn't unless I learned humility but I learned humility in my 50s in a way that I really appreciated yeah and I wondered how much modern is also just saying like I'm not old elder implies old but modern elder implies something different and nobody wants to be seen as well don't we like juxtapositions?

18:04it makes it more interesting And so modern elder speaks to both the age-old perspective on elder, but also the idea that there's a new version of a modern elder. And I think in an era where we have longevity, not in the US so much right now, that'll come back. But worldwide, I mean, the longevity is skyrocketing post-COVID still. And so we are going to be living longer. So the idea that someone's in their 50s, 60s, 70s, 80s, and they're going to be both a mentor and an intern, whether it's in the workplace or just in their community, I think it's valuable. Well, I like this idea of a mentor. There's a Seneca line.

18:43He says, we learn as we teach. Yeah. And the idea of this sort of you're getting as much as you're giving. Oh, for sure. And if you see it as this two-way street, then you get better and they get better. the problem I think is, is if you feel like your wisdom, uh, entitles you to teach, but you're not open to learning. And I think the best mentor mentee relationships, it's the, the, the more experienced person is explaining all their experience. And then the new person is bringing the younger person is bringing their energy, their, uh, you Their sense of what's popular and new, their curiosity, their fluency with things that are recent.

19:26That's exactly right. That's the exchange. Well, the exchange. So for me and Brian Chesky at Airbnb, it was an EQ for DQ exchange. And Brian had the DQ, not Dairy Queen. Although, frankly, out here in Bastrop, you've got a Dairy Queen, I'm sure. Yeah, we do. But no, DQ as in digital intelligence. I didn't have digital intelligence. I was 52. I barely knew how to work my iPhone. But more importantly, I didn't understand product. I didn't understand websites. I didn't understand UI, UX. Didn't understand millennial travel habits. Didn't understand even venture capital in Silicon Valley because my boutique hotel company didn't take venture capital.

20:02So I learned a lot from him. He learned emotional intelligence, broadly speaking, around leadership, around culture, around strategy. I mean strategy was less emotional intelligence. But so there's a lot we learn from each other. And I think that's really the ideal kind of relationship. You know, Ryan, by the year 2025, the U.S. Department of Labor – by 2025, the U.S. Department of Labor says that the majority of Americans are going to have a younger boss. Now, we've never seen this before. Yeah. Right now, it's about 45%. So 45 % of Americans have a boss that's younger than them. Yeah. Now, most didn't have a boss that was 21 years younger than them, like I did.

20:45Sure, sure. But the truth is that we're moving into an era where we have five generations in the workplace and we better create a new generational compact or like a potluck where everybody brings to the table what they do best. And sometimes that may mean a younger leader or manager is going to have an older person working with them and there's a symbiotic relationship that can happen there. And frankly, if the older person isn't willing to have that and wants to say, like, I've paid my dues, I shouldn't be reporting to someone 10 years younger than me, they're going to get a lot of OK Boomer.

21:15Yeah. Because that OK Boomer was whole, the whole premise of that was like, you're telling me the way the world used to work. Or it's like mansplaining. Yeah. You're telling me something as if you know, but you actually don't know. Right. And that's one of the most, that's a particularly frustrating vibe. It is. When the person thinks they know and they don't know. Yeah. Or they think they know and they're, because of that arrogance, they don't know that you already know. Right. Right. Or there's just the lack of curiosity. And I think that's really what it is. And that's why this idea of curiosity and wisdom, the alchemy is particularly important as we age, because two of the most common variables associated with living a longer, happier life are curiosity and openness to new experiences.

22:03So one of the questions I like to ask myself, and we ask at MEA at the Modern Elder Academy, is what do you know now that you wish you'd learned or done? What have you known or done now that you wish you'd learned or done 10 years ago? And then imagine 10 years from now, what will you regret if you don't learn it or do it now? Because anticipated regret is a form of wisdom. And so that's the kind of thing, you know, Seneca talking about, you know, we don't have a short life. We have, you know, we have wasted time. We don't have, life is not short. He says we just waste a lot of it. Yeah. And I think that's very true.

22:40And so what we can especially learn to do with a growth mindset in midlife is to say, okay, I learned how to surf at 57 because of that question of like, okay, at 67, it's gonna be harder. I learned Spanish because guess what? I'm living in Mexico part of the time. And I learned French when I was younger. So I'm going to learn Spanish at 57 because it would be harder at 67. So being able to anticipate a regret and then take it back to say, oh, that's a catalyst for me actually learning something or doing something now. When I think that's something that mentors and elders can really help us with is the idea of like, hey, I wasted eight years of my life going down that dead end where I've tried that before, or I persisted way too long trying to do X, Y, or Z, right?

23:29And then they can go, you're not going to get it right now, but maybe me explaining this to you, it's going to be only three years for you. Or you're only going to do it, you're not going to do it until it blows your marriage apart. You're going to catch yourself, like the idea of going, hey, I've been down that road. I know what's there. And part of it, you're going to have to learn by experience. But hopefully my experience will help you recognize what you're experiencing sooner. And it can just shave some of that painful trial and error out of it. A great mentor is a wisdom accelerant. And that's what we all need in life.

24:07I've been doing something since age 28. And who knew I was going to be doing that? And many years later, having a midlife wisdom school. At age 28, I had been running my boutique hotel company for two years. We had the Loma Prieta earthquake in San Francisco Bay Area. Bay Bridge personally fell down. And bottom line was there's nobody coming to town. I had one hotel at that point. And I was a 28-year-old idiot CEO who didn't know what to do, and I was running out of cash. So one day a friend of mine said, hey, stop complaining to me. Just write in a journal. So I took a journal off the wall, off the bookshelf, and I started thinking, okay, I'm going to just journal.

24:44But I did something different. I wrote on the cover of the book my wisdom book. and I started a practice that I've been doing now for 35 years, which is every weekend I sit down for, you know, 20 to 30 minutes and I write down my key lessons of the week, professionally and personally. The things that actually, frankly, often were painful because our painful life lessons are the raw material for our future wisdom. So I would actually sit down and write down, okay, I put that idea out to my leadership team, but the two critics in the room who are always critics, like said all kinds of terrible things about it.

25:22My lesson to myself is why don't I go to the critics before I present it to the whole group to get their fingerprints on it. And so like, okay, let's try that. And it worked. But anyway, at 28, that sounded, I mean, at 63 now, I get it. But at 28, I didn't know that. And so what I do is I make bullet points of the key lessons of the week and then how it will serve me in the future. Sure. And what journaling does is allow you to see patterns. Pattern recognition is wisdom. Yeah, of course. And so the bottom line is this is something I've been doing. And then I brought it to my leadership teams at Joie de Vivre, my boutique hotel company at Airbnb, and now at MEA, Modern Knowledge Academy, where once a quarter, we sit down as a team and we say, what was each of our biggest lessons of the quarter and how will it serve us moving forward?

26:12Number one. Number two is what was our biggest team lesson? And so I'm a big believer. Peter Drucker coined the term knowledge worker in 1959, saying that the world will be ruled by knowledge workers with computers. And he was right. But the truth is we sort of moved, I think, to the wisdom economy instead of the knowledge economy, because in an era of AI, where knowledge - Facts, figures, info is going to be a commodity. It's all commodified. Yeah. So wisdom becomes the scarce resource. So how do we create wisdom workers? How do we create wisdom management and wisdom practices? So what I just described here is the wisdom practice of a leadership team, sorting through what was learned in the last quarter, sharing it, because it's a vulnerable process.

26:55but also it means that your skin knee means I won't have to skin my knee because I'm learning from you. Wisdom is not taught, it's shared. And being able to sort of understand that is so critical in the era we live in. So going back, what do you wish you knew or did sooner? I mean, there's a long list in what part of my life. Obviously, I just mentioned surfing in

27:25earlier. I had a, I had a foster son when I was 28. Um, I became a foster son to a 13 year old, um, African American kid, uh, in San Francisco who my first hotel was in the Tenderloin in San Francisco. He was a, he ended up being, being in a group booth home and, um, I was mentoring him. Yeah. And then he said, I want to be your dad. And I was like, okay. And so that was really interesting and challenging because he had a really difficult, uh, upbringing. Sure. Um, Um, and, and I'm still in his life and it's been, but it's been a hard, that's been a hard road. I'm gay. And so it's like, okay, how am I going to be, how am I going to have kids?

27:59Well, you know, I'm now 63 and I've got kids who are soon to be 13 and 10. Um, I'm sorry, 12 and 10 and, uh, 12 and nine. Yeah. Chip is like, I'm like doing my math ahead because they were both getting, they both have birthdays in the next week, uh, next month. Bottom line is I wish I'd had biological kids earlier. I had them with a lesbian couple in Houston. And so that's part of the reason I come to Austin and Houston a lot. That's so sweet. But I wish I'd had my kids earlier because – You would have been younger or you would have started – you would have had more of the time with them. I'd say it would be two things.

28:38One is more time. And that actually is coming. So that's the good news. but also just to know that you know by the time they're getting married i'm gonna be in my 70s you know or maybe even 80s who knows and i would love to have had that happen earlier in my life but i love the relationship with them i mean it's been i as someone who came out at age 22 i sort of immediately thought like i'm not gonna have kids right um and we now live societally that wasn't as accessible or that's right that's right that's right so now we live in an era where it's like very accessible and more accepted. And yeah, so I, I, so I would say that's probably one of my biggest regrets.

29:19I can't, I can't do a do over on that one. No, I think about that too. I had kids when I was 29, which people thought was very young. And I was talking to someone yesterday who had their kids at 21, which maybe feels a little young, but I, I, it so changes you and it opens you up in all these different ways. And it forces you to get serious about things, address things in yourself, it also, it gives you a kind of a purpose and it gives you, um, it gives you like a sense of what like matters, you know, um, that you can't help but think what would it have done to me to, what would have done for me to have learned these things earlier?

29:55Maybe you couldn't have, maybe you would have not learned the lessons till later, but, but you, you see how much it transforms you as a human being and you go, why did I wait as the old me? I mean, yeah, it definitely forces patience. It forces getting out of your ego and being open to being, you know, giving presence. You know, presence is a really important thing. Although in the world we live in with all the gadgets we have, you know, absence is sort of the opposite of presence. I've been saying that the secret to being a great parent is presence. You have to give them lots and lots of presence.

30:30but it's the other kind of presence right it's actually being there so it's like so true when you're like when you're with your kids be with your kids that's right right and how much uninterrupted time the phone you're not doing two things at once you're not checking the phone you're actually entering their world and engaging in it which is actually allowing you to go back in time right It's allowing you to occupy the mindset, the curiosity, the fun, the joy of a child, which is, I think, making you younger. It's a happier place to be, quite frankly. And so the more you give yourself that, the happier they will be, but also the happier you will be.

31:13Yeah. And we are all the ages we've ever been. Sure. It's just that as we move into adulthood, we sort of forget that. and kids help us to remember that. And there's no doubt about that. Yeah. There's a story about Winston Churchill. He's in the middle of the Second World War and he walks in on Downing Street and he sees this sort of staff member. I think it was like a military actually setting up a train track for his grandson. And Churchill's just sort of watching him. What's he doing? And Churchill sets up, the soldier sets up the whole track. Then Churchill gets down and he goes, put a train on it.

31:53The guy's like, okay. And he puts a train on it. And he's like, now put another train on it. And the guy does it. And he goes, now let's have a crash. And it's like, here you have this guy in the midst of this incredibly stressful moment. Literally the weight of the world is on his shoulders. And he's going back in time to enter the world of a child or his grandchild. And just what an immense relief that is. In the same way, I think if you're a successful, busy person, you should have some sort of physical practice that keeps you energized and young and present. Having a family practice is also a huge part of that.

32:32Like where you play Legos or jump in the pool or you do just crazy kid stuff. Well, I think it was Plato who said you could learn a lot more about a person from an hour of play than from a year of conversation. Sure. And I think there's two – I mean that's one actually interesting segue. That is one of the number one things I've learned from teaching at a midlife wisdom school is how essential play is or experiential learning is to come in the back door to have someone learn something. So especially the most important learning that I think people need in the middle of their adulthood is how to become a beginner again.

33:13Yeah, sure. Because that allows you, first of all, moves you out of the fixed mindset of trying to prove yourself and win and recognize that you want to improve yourself and learn. And that process allows you to become a newbie again. Yeah. And that allows you to feel fresh. and there's a bunch of research that has shown that part of the reason that younger people have, it feels like life moves slowly for them during the summer is because they have so many new activities. So there's the freshness of first-time experiences tends to actually prolong time. It's when you have, we don't have fresh new experiences, life starts to actually feel like it's accelerating.

34:02And so one of the ways in midlife for people to help to understand how to live a life that feels more deep and rich, because we're getting better at the, how do we live a longer life, but how about living a deeper life? And that is like trying new things that you haven't tried before.

34:25You probably heard the headlines about all the different cuts to foreign aid and food benefits. This is having a profound impact on the world's poorest people and the world's poorest communities. But, you know, just hearing about that, that's not what stoicism is about. Stoicism is, to me, what you're going to do about it. And that's where GiveWell comes in. GiveWell is trusted by tens of thousands of donors each year because they provide free and independent research that helps you understand how to have a big impact. GiveWell has spent the last 18 years research in global health and poverty alleviation, and they direct funding to the highest impact opportunities.

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35:39To claim your match, go to GiveWell.org and pick Daily Stoic from the drop-down menu under podcast. That's how they know that you heard about GiveWell from the Daily Stoic, and you'll get your donation matched. That's GiveWell.org, code the Daily Stoic to donate or find out more. Look, if you're listening to this podcast, you've probably heard of HelloFresh, right? They're the number one meal kit in America. They make home cooking easier with chef crafted recipes and fresh ingredients delivered straight to your door. This fall, they're serving up even more to love. It's not the HelloFresh you remember.

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37:29They might tell you something like, you don't have to learn anymore. Oh, no. Right? Like, because they notice that their parents never have to go to school. Their parents don't take any classes. Their parents don't have homework. Maybe they never even see their parents read. Yeah. Right? And so there is this sense that education is this thing you have to do when you're young. Right. And then thankfully, mercifully, it ends. Yeah, yeah, yeah. Which is, of course, a terrible lesson to teach children. And it's a terribly sad way to define your own life, right? One of the great stories about Marcus Aurelius is he's, you know, he's the emperor of Rome.

38:06He's an old man. And he's seen leaving his palace. and his friend stops him and he says, you know, where are you going? And he says, I'm off to see Sextus the philosopher to learn that which I do not yet know. And the guy goes, this is incredible. You have the richest, most powerful, wisest person on earth, you know, taking up his tablets and going to school. And what a powerful example that is. And tragically, how unlike most of us it is. Like, when was the last time you learned something new? When was the last time you were a beginner? When was the last time you picked up a book about something you knew nothing about and you're like, I have no idea what the fuck is happening.

38:43I'm going to have to do so much reading and learning just to figure out what is here. Like where I have to like, where I have to like look up words or when I have to go to Wikipedia just to get like a basic understanding of terms and ideas just to like understand what's happening. That's uncomfortable and strange. It's also invigorating, but it's easier to, it's easier to not do it. And then it's easier if you are going to read to just read another thing about something you already know a lot about. Yeah. My favorite question to ask at a cocktail party is, what in your life are you a beginner these days?

39:18And people head for the bar pretty quickly. Because it's like, oh, that's a deep question. Like, what are you asking these questions for? But it's an important question. Because to not be a beginner is your missed opportunity for exploring what it means to be a kid again. Because we were a beginner. We get self-conscious at some point. And the little child who's moving from crawling to walking is not self-conscious. But at some point, we need to move from crawling to walking in other parts of our life. But we're so self-conscious and maybe self-critical, not just focused on, for me, it was yoga.

40:02I love meditation. I've been doing meditation for 40 years. I was on the board at Esalen. That's where I learned yoga. I'm sorry, I learned meditation 40 years ago. Love it. But I was terrible at yoga and I had a mindset. The mindset was like, oh my God, I'm more lumber than limber. I'm not good at yoga. And it was partly because with meditation, I closed my eyes and I was not doing any social comparison. So social comparison is like the recipe of suffering. And when it came to yoga, I was in a room in California with a bunch of yoginis who could do things with their bodies I can't do. And so I got stuck.

40:40And the stuckness was like, okay, the trigger was the social comparison. What I came to realize over time is the number one thing I needed to do was I can do yoga without anybody else in the room. Or I can do yoga with my eyes closed. Or I can do yoga. There's lots of ways I can do this to not let the trigger shut me down. Yeah. And so that's what I've been doing. And I think being able to see our triggers, what's the trigger that shuts you down from trying something? And again, it's, you know, whether it's the sense of failure, the sense of disappointment, the social comparison, the fear of safety, there's lots of things that can be triggers.

41:18But once you've identified it, then you can sort of like work around the trigger. Well, ego is such a problem, especially as you get older and more successful because you're used to things being the way that you want them to be. You're used to people seeing you a certain way. You're used to seeing yourself a certain way. And so to be a beginner is to strip a lot of that away. To do something you're bad at is to strip a lot of that away. To explore the unknown is to strip a lot of that away. And so you can kind of, you kind of become a prisoner of your own success and that you can't or you won't do anything that is not inside or related to that success.

42:00Yeah. And you're used to only being in rooms that you're invited to be in. You're used to being the center of attention. You're used to people caring. And so one of the nice things about being a beginner and stuff is you go like, usually I would be at the head of this room or class. And actually now I'm the humble student. And nobody cares about me. nobody like to have to just flip the hierarchy or this the status is is really it's scary but again invigorating and it's what creates both growth and i think it shrinks the ego which is a good just generally yeah so richard roar is uh you know richard of course and and he's a mea student he came to me at 78 years old in baja to actually as a student and now he's a teacher for us at our Santa Fe campus in New Mexico.

42:55He and Carl Jung have both said that the first half of our adulthood, the primary operating system is our ego for all kinds of reasons. And it's around midlife that the primary operating system moves from the ego to the soul. But nobody gives operating instructions for this new operating system. And of course, your mileage may vary. I'll never forget. So I'm gonna tell the audience here the story of when I met Ryan. It was at Summit. but, and, and Ryan. On top of the mountain, right? Yeah, top of the mountain. I think so. And then, and it was four or five years ago. And Ryan was there as was Kevin Kelly.

43:28And Kevin Kelly got up and gave us talk about technology. And he's in his mid to late sixties. And then Ryan gets up and talks about wisdom and philosophy. So it was, it was such a weird juxtaposition. The old guy was talking about technology. The young guy was talking about wisdom and philosophy. And I loved it. And so for, for me, thinking back to this idea of, you know, you can, you can be wise at any age. We know 70-year-olds who just are not wise because they haven't metabolized their experience. I think wisdom is the metabolized experience which leads to distilled compassion. And so learning that you are supposed to actually let go of your ego doesn't mean you actually get rid of it.

44:11I think of it like a dance. So in sixth grade, I went to ballroom dancing. I went to ballroom dancing school. and it was more like learning masculine and feminine roles more than anything but you learn the techniques and the things and so yeah the the boy is leading the girls following and that's sort of what the ego and the soul have done in the early part of our adulthood and it is around midlife midlife divine broadly which is now some sociologists saying 35 to 75 so you are in midlife officially, just barely, that you have the opportunity to change who's leading the dance. Yeah, sure. And the soul then leads and then the ego follows.

44:52It's not there anymore. And you can have a sense of humor about it. And it actually does provide, ego provides all kinds of great qualities for us. Yeah, the idea that you can eliminate the ego is a very egotistical thing, right? To me, it's like I have a temper, but I don't have to make decisions out of anger, right? Like I can recognize why I'm feeling what I'm feeling. This is what you learn in meditation. This is what you learn in journaling is like, here's what I'm feeling, but that doesn't have to be what I do. Or here's what I'm thinking, but I don't have to agree with those thoughts or codify those thoughts or whatever.

45:27And so understanding like, hey, I have the ego and the ego is telling me I'm not good enough for these reasons or I'm better for these reasons. I'm resistant to hearing what you're saying out of ego and then to go, okay, I'm going to take a breath and I'm going to say, actually, I don't want my ego to be in charge here or to lead here. I'm going to step back and let a different part of myself, I'm going to open up a different part of myself. I'm not going to let ego come between me and this potential lesson or this potential connection. I'm not going to let ego drive me into this cliff or off this cliff.

46:01And so understanding that the ego is there, you can't eliminate it, but it doesn't have to be in charge. No. And it doesn't have to be so reactive. Viktor Frankl, who Man's Search for Meaning is one of my favorite books. He wrote between stimulus and of course, in a concentration camp, it's easy to be reactive. But he wrote between stimulus and response, there is a space. And that space is our power to choose our response and in our response lies our growth and our freedom. I think that one of the things that we ideally learn as we grow into our adulthood is we learn how to become a first class noticer of ourselves and to create that space between stimulus and response.

46:45Because often it's not stimulus and response, it's stimulus and reaction. Sure. And the soul doesn't react. The soul responds. yeah the ego reacts and so learning how to create that space and and there's the language for it in social science about emotional moderation something that actually does tend to get better with age yeah um so these are things that we can learn but we can train them like that's the part that's like that's what we have to learn it's like okay it's not just a matter of having it happen just like wisdom can be accelerated so can eq your emotional intelligence well you also have as you get older you have a larger and larger body of evidence that's right right so you you go you can really ask you can really see whether something is working for you or not yeah you know like as i've gotten older i can look back and go hey have i ever been glad that i lost my temper you know like i now have decades of experience of getting pissed off and reacting and how many times afterwards am I like I'm so glad I did that it's like effectively none basically zero and so you you can go hey um I know more about myself and I have I've I've tried it this way I've tried it this way I've I tried it this way uh without fail for 25 years yeah and it's not gotten me any closer to where I want to be and and so what you have is this kind of sense of it's no longer this theoretical or abstract or philosophical, do this, don't do this, this is bad.

48:22You go, no, that doesn't work for me. And that is a really important form of awareness and wisdom, I think. We do, one of the things we do at the Modern Elder Academy, MEA, is designing your own hero's journey. And so using Joseph Campbell's work and looking at what would it look like to understand the three stages of the hero's journey, which is starting from the default place, the normal place, going into the call to adventure, which is where a lot of our shadow side comes out. And then coming to the other side, you know, a renewed person with a new pair of glasses. And so it's often in that shadow side, that messy middle, that's the second stage of the transition through the initiation process of a hero's journey, that you can see your patterns.

49:09So one of my patterns is I have a very long – I have a lot of patience generally with people. I have a very long fuse. But then it gets to a place where it's like it's just like no more. Yes. And so I get to a place of resentment. Yeah. And I tend to be – and so underlying this my own review of my own hero's journey was understanding that, okay, what happens with me is I tend to have a calling. and I get very passionate and sort of like the passion of the Christ. Then I sacrifice and then I get one-dimensional and then I get on a treadmill and then I go to my archetype that is natural for me, which is the can-do hero.

49:52I can do it and we can do it and I can't. And it's very ego-fed. And then I get to a place where I'm like starting to burn out and then I get resentful because people are not keeping up with me. It's a classic African proverb of if you want to go far, go to if you want to go fast go alone if you want to go to far go together yeah i'm a fast alone kind of person in terms of how i do things a lot and so i get resentful because people aren't keeping up with me and i'm like i feel like the whole weight's falling on my shoulders and then i have to like get to a place of thinking oh okay renewal massage meditation walks in nature with my dog and i get back up to the top of this circle which is not can do it but conduit how does something come through me?

50:37How does something come through me? And how do I create the channel for something to come through me? And then it's like, oh, opposite side of ego. So long story short is I think understanding your patterns. And for me, I had to work backwards from resentment. I get to resentment. That happens. Like what are the - When could it have gone differently? How could I have averted that? What would it be the thing that I could have done earlier that would have not gotten me to that place? And so, you know, whether it comes to your temper or whatever it is, like what are the elements that, because those are the early warning signs.

51:10And early warning signs are a form of wisdom. Being able to see the pattern recognition. So, you know, okay, I can see what path I'm on because we're very good observers of other people. Not so much of ourselves. Although I think the Stoics are so spectacular at this. That's part of the reason I loved reading Marcus Aurelius in college because it gave me a sense that reflecting, having space for reflection is essential. Yeah, it's essential for leaders. You imagine the incredible stress and the isolation of being the emperor of Rome, the sheer

51:50unhealthiness of that position even, right? One person shouldn't have that much power. Yeah. And then, you know, his reign is basically one unexpected disaster after another. There's a pandemic. There's floods. It's these wars that he didn't want. There's betrayals. He has issues at home. And so it's on those pages that he's working out those feelings instead of working them out on other people, working them out through bad decisions, you know, working them out or pretending they don't exist. And so that the process of like thinking about it, stepping back, you know, And imagine he's just, Marcus Reuss would famously bring his journals and his books like to the Coliseum.

52:36Like he had no interest in the gladiatorial games, but he was forced to go. And he would be, you know, doing, he's just taking a few minutes wherever he can get to just get some distance between him and the moment that he's in to think. And that is, you think about the impact of doing that over the entirety of one's life. Just what kind of insights you would have. And that's why I think meditations has lasted for thousands of years is that it's so specific. It's one person's discussion with themselves. But because it's so specific, he does such work getting to know himself. It becomes universal and timeless.

53:16No doubt. I mean, I think the question that I like to ask people is, so what is your mindfulness practice? And people sometimes get like, oh, I don't have one. And then I say, well, so what do you do that actually gives you timeless awareness? You might know flow as the language you would use for it. But like, is it journaling? Is it gardening? Is it cooking? It could be riding your bike. It could be working out. Walking with your dog in nature. For one of my co-founders at MEA, it's surfing. Yeah, sure. But he never thought of it that way. He's like, okay, mindfulness is meditation. It's yoga.

53:56and it's all that other stuff that people who, you know, new age people do. And he didn't realize that surfing was sacred for him. It was something that actually got him out of his mind, out of his ego, and seeing awe. And awe is really a pathway for us. And Dacher Keltner is on our faculty, amazing guy, Greater Good Science Center, UC Berkeley professor. He's shown like the eight, his book earlier this year that came out called Awe, showed the eight common pathways of awe globally. and you'd think that number one and number two on that list would have or i'm sorry number one on the list would have been nature it was actually number three which is interesting but number one and number two on the list were pro-social human-centric things number one on the list was moral beauty awe you felt awe because you saw courage kindness temperance many stoic qualities you saw the best in human nature.

54:52And number two on the list was collective effervescence. When your sense of ego separation dissolves and your sense of common joy emerges. And so what Dacker helped me to see with MEA, with our Modern Elder Academy, was like, oh, we are doing that every week. Every week we have a cohort of 24 people coming together in Baja and now in Santa Fe. And they're feeling a lot of moral beauty and collective effervescence. And they're realizing like, wow, my form of mindfulness might even have other people involved in it. Yeah. And wouldn't that be beautiful? Sure. And so, yeah, I think we, it does require people to shift their habits though and learn how to do what I call the great midlife edit.

55:42Yeah. Just like in order for you to make space in your life to be able to try these new things, you have to have a constant discernment process to say, what are you letting go of?

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57:01That's A-U-R-A-Frames.com, promo code STOIC. This deal is exclusive to listeners and frames sell out fast, so order yours now to get it in time for the holidays. Support the show by mentioning us at checkout. Terms and conditions apply. I'm picking my kids up from school today and then doing our weekly routine, which is I take them over to Whole Foods. We get all our groceries for the week. Then we have dinner. It's one of their favorite things to do. It's one of my favorite things to do. And then my wife loves it because she doesn't have to take care of it. This holiday season, whether you're a guest or hosting the big dinner, Whole Foods Market has what you need to delight everyone at your table.

57:37They even have heat and eat sides from the prepared foods department. You can make Whole Foods your one-stop shop. Everything follows Whole Foods Market's strict ingredients standards so you know it'll be delicious and good for you. You can also order online for pickup and even delivery in select zip codes to skip the crowds. Shop everything you need at Whole Foods Market, your holiday headquarters. I'm curious what has midlife and all the experiences you've had what has it taught you or how has it changed your relationship to money because you had a successful business you exited that business then you had this time in Airbnb which was incredibly fast-growing enormous company and then you've you've I'm sure met a lot of extremely wealthy people met a lot of people who are not wealthy.

58:26How, how have you, how's your relationship or your understanding of money evolved? One of the questions I like to ask in a workshop is you have a, you know, you have a lifelong relationship with money. Yeah. So you're, you're like in a relationship. Yeah. So what if you went to relationship counseling with money? Sure. What would money say about you? And what would you say about money? Because does money give you freedom or does it take it away? I think the key to understand money, I'm a big fan of Lynn Twist who wrote The Soul of Money. She's on our faculty. And what I love about her work is she sees money as a currency or a channel for something that you want to see in the world.

59:06So it's very much what do you do with it? All it is is the – it is this intermediary that allows you to create the world you want, whether that's selfish or whether that's altruistic or whatever it is. And so my relationship with money is interesting. I had a money avoidant. This is so strange. People don't expect this of me. I had a money avoidance point of view. So there's money scripts. Yeah. And I had a money script and mine was sort of like, oh, money, money is sort of dirty. And, but I was, I had that when I was growing this big boutique hotel company. So I didn't, what I really, you know, took at my shadow side during that time, it was not like, I want to be as rich as possible.

59:46I actually didn't care about that. but money was my currency to create ambition and success and i wanted you to see me as successful so i was an admiration addict um and so you wanted to have stuff that people didn't want stuff i wanted to so it didn't matter in terms of like cars or homes or you know things like that what mattered to me was oh i have this company and all these cool hotels that are in the newspaper You wanted people to admire the empire that you built. That's correct. That's correct. And so for me, money gave me the ability to do that. But it also scared me because I'd seen people I knew who got really attached to the money and especially to the spoils, the treasure that they would be able to buy as a result of that.

1:00:34So when I sold Joie de Vivre, I sold it at the bottom of the Great Recession. So I sold it for so much less money than it would have been worth four or five years later. so it was like okay i did fine but it wasn't like i you know i was gonna be set for the rest of my life i still owned a bunch of hotels which that helped when i joined airbnb i told the airbnb guys like you know what i just i'm doing this because i think this is interesting yeah don't pay me just give me some stock options that invest in six months if this doesn't go well i'll just have that and let's try this out for six months because brian and i are gonna have to figure out like do we have a good relationship so we didn't tell the press for six months but about a few months into it, I said, I'd like to do this.

1:01:13Like I'm going to do it full-time instead of just part-time. And long story short is I got some stock options and I got paid a salary that wasn't very large. And I didn't really care because what I really loved was I really loved moving from being the CEO to being the CEO whisperer and to being sort of not the sage on the stage, but the guide on the side, this person who was helping the founders of Airbnb be as successful as I could. And as it turns out, it turned out to be financially incredible. And that's allowed me then to see money now for the last six years with MEA, Modern Elder Academy, to, I don't pay myself.

1:01:54And I just, you know, I don't have investors at this point. It's just like, I'm funding this whole thing because it's my way of giving back. I lost five male friends to suicide between age 42 and 52 during the Great Recession. And I was going through my own challenges during that time as well. And so I just had this strong feeling in my gut when I finished my full-time work at Airbnb that what I really needed to do was create a midlife wisdom school, a place where people can reimagine and repurpose themselves because I wanted to create that reflection space. There's a woman named Mary Catherine Bateson whose mother was Margaret Mead and father was Gregory Bateson, the psychologist.

1:02:36And she coined a term, the midlife atrium. And what she said is like, what we have in life today is we have additional longevity. But the way society looks at that is you're old longer. It's like you have two additional bedrooms in the backyard of life. But she said, that's not it. You're in midlife longer. And what that means is you need to re-architect, create a new blueprint for the home that creates a space around age 50 or so to have maybe a gap year or something that allows you to say, how do I want to live the rest of my life? Because - Because you can't keep using the old assumptions that you had about yourself and where your purpose and your meaning and all this stuff was because now the world is different and you are different.

1:03:20And you maybe have, you've been living out somebody else's success script, your parents' success script or whomever's. And so it's that opportunity. The average age of people who come to MEA is 54, but we've had people as young as 25 and as old as 88. The average age they think they're going to live to is 90. 54 is exactly halfway between 18 and 90. And so it's halfway through adulthood, but most of us at 54 don't think like, oh, I've got half of my adulthood still ahead of me. And so the memento mori piece of being 54 and sort of seeing your parents pass away, seeing friends pass away, having health issues that come up.

1:04:01Sure. That Memento Mori helps people, and Laura Carstensen at Stanford has shown this, that when people actually have a shorter time horizon for their life, they are more in the moment. Yeah, sure. They're less focused on the future. Sure. And by being more - Deferring. That's right. Pretending they'll get to it later, when I'm ready, after this, you realize like, if I'm going to do this, I have to do it. Yeah. So to be able to actually have that memento more a perspective of like seize the day, be in the moment, while also seeing that, you know, science is helping us to live longer is beautiful because you have this, it's a bit of cognitive dissonance, but it's actually works because there's a side part of you that says like, okay, I'm, I'm going to, I'm going to focus on the moment.

1:04:47And at the same time, I'm going to live a long time. So the longer you are going to live, maybe the better you're going to take care of yourself. maybe the more willing you're going to be to be a beginner. Maybe you're going to actually save enough money to handle, you know, 20 years longer years of life than you were expecting. And so it's that juxtaposition of how do you help people to get into the mindset of being in the moment, but also realizing you have a lot more life ahead of you than you thought you did. Yeah. My, my friend, Sepp Kambar, he did this cool study. This was like 10, 15 years ago.

1:05:19So I don't even know exactly how you do it today. But when, back when people were writing blogs all the time he had this he created this thing that indexed and it crawled all like hundreds and hundreds and hundreds of thousands of articles that people had written like unsolicited basically journal entries and he found and this this is more or less confirmed with academic studies later but young people tended to associate happiness with achievement yeah i just got this new job i just got a raise i just climbed mount kilimanjaro right and then older people their feelings of happiness were almost always associated with some form of contentment.

1:05:56My kids are visiting, had this great Thanksgiving. We watched the sunset. And so I imagine that as you get older, part of what's happening there is you did the achievement stuff. Yeah. And it felt nice, but you realized it wasn't everything you thought it would be. Or you realize there's a certain amount of diminishing returns to it. That you did one company, a second company isn't going to feel, even if the second company is more successful, it's not going to feel twice as good. It's going to feel half as good. And you realize that you can't just do more and more and more and more and feel better.

1:06:32No, actually, you're bumping up into the inherent inadequacies of external things, of accomplishments, of achievement, of recognition. And you're realizing that happiness has to be rooted in something deeper and probably more communal. It's so true. There's a term, the hedonic treadmill, which speaks to this idea that you just go out and you, interesting there, a declaration of independence in the U S is says the pursuit of happiness. And the word pursuit in the dictionary says to chase with hostility. Do we chase hostility, happiness with hostility at the mall at Christmas time? We do. Bottom line is J.D.

1:07:10Salinger who wrote the catcher on the right said, wrote happiness is a solid, the achievements and joy is a liquid. And what he meant by that was that often happiness is the thing we're striving for. It's very tangible. You know it when you've got it and it maybe motivates you. But joy or contentment really comes from a place inside a little bit more. And it's a little bit more ephemeral. And what brings it, I like to think of joy as a guy who started a company called Joie de Vivre. I like to think of joy as something that's inside and it's something that emerges. is you know we say joy is bubbling up yeah as if it's inside of you um it takes some time to get to that place in your life where you know what actually brings the joy yes sure and to be able to there's a term in social science called environmental mastery and it doesn't has nothing to do with eco ecology it's the idea that you know the habitats in which you're going to flourish it's particularly focused they focus on it in occupational kind of things in terms of like what kind of culture, company culture, but it's true across everything.

1:08:22Environmental mastery is something that gets better with age, you know? And for you, I mean, again, you were like, you're precocious, you're ahead of your game, but you knew you didn't necessarily want to live in Austin. You wanted to live out here, you know, out in the country. And in the future, you may have a different point of view, but to be able to know what it is that makes you happy or gives you that sense of joy is something that I think we develop over the course of time. Have you read David Brooks's book, The Second Mountain? Yeah, of course. I think one, we were talking about money earlier.

1:08:55I think very rarely is the second mountain primarily financially motivated, right? And so obviously I've had this, I had a business career and then I've had this writing career. And then as we were kind of, when we were doing this bookstore, it was actually very helpful for my wife and I to sort of go, this is probably a terrible business. But that's not why we're doing it, right? Like, we're doing it because success is going to be measured here on a sort of a wider set of criteria. But you still can find yourself, oh, we're sales today. Obviously, sales can't be zero for too long, or you go out of business and you can't continue to do the thing.

1:09:33It's not a charity. But the decision to say, hey, there's a choice, right? Do I want to, I could build a big consulting agency. I could have built out my marketing business. I was like, this isn't doing anything for me. This isn't what gets me excited. That's not what I want to spend my success on, right? And so I think as you get older, you have these options of where you're going to put the success, the power, influence, relationship, all the things you build. What are you going to put it towards? It probably shouldn't be another thing that makes a lot of money. It should be a thing that makes a lot of difference.

1:10:12Well, you know what? It is what the person wants it to be. But I do think that we move from ROI, return on investment, to ROI, ripples of impact. Yeah. And a ripple of impact means that could be – there's so many forms of ripple of impact. And that's what I look at. And for me, with 4 ,000 alumni from 44 countries, this is the thing that I want to do the rest of my life. I mean, learning how to become wiser, man. I mean, you and I have sort of like, you know, funny enough, are you 36? Yes. And I'm 63. So we have like juxtaposition of the numbers of our ages, but also juxtaposition of what we're doing.

1:10:53I mean, the idea of being in a career that incentivizes us to become wiser. Yeah. And we share that with others. I mean, that's, I don't know. If somebody had told me that this was a possibility a few years ago, same with you, I'm sure. You know, like, you know, when you're at American Apparel, you're like, really? Am I going to be doing that? The other thing that happens that's kind of humbling is like, and I'm sure this is for you, it's like you built this huge hotel chain and then you sold it. And then you just get this inquiry, you go consult to this company. and maybe what you work, your compensation at Airbnb may have dwarfed the things that you did previously, right?

1:11:37You have this like decoupling money from success and also your own role in it is really humbling but also empowering. So it's like I've made investments or advised on things and I look back, I go, I made more money on that conversation I had than a book I spent three years of my life on. Yeah. Now, that's a great thing because now I can go spend three years of my life on another book and not have to worry about going like, hey, I'm not necessarily thinking about return on investment of everything I do. And also going, hey, I don't actually know what is going to work and what's not going to work.

1:12:18I'm just going to do what interests me. and I'm going to understand that if you have a portfolio of things that you're pursuing, doing this thing over here, I'm doing this. One of those things is going to be really right and going to pay for a lot of the things that you're not so right about as long as you're doing the things that fulfill you and you think are having a positive impact. And ideally, you become successful. And Casey Neisatz said to me once, he's like, we don't do work to make money. We do work. We make money to do more work. His point was like, how do we do cool stuff to fund the stuff that isn't going to fund itself?

1:12:56And I think that's a really awesome place to be. That unless your parents had a ton of money or you hit the lottery or your tech company IPO'd when you were 22 years old, you're not in a position to think about that when you're 23. because you don't have the safety net or the base that you've secured for yourself that now as you've gotten older, you've done this longer, it should free you up to take more risks, to do more stuff, to put yourself out there and subsidize yourself or other people. That's a great position to be in. Yeah, I think, and I think money, yeah, money is a challenging topic for so many people.

1:13:31And because, you know, it's about keeping up with the Joneses. And I mean, there's this fascinating study where they asked people if you could earn$50 ,000 a year and you earned more than the people around you, or you could earn$150 ,000 a year and you earned less than the people around you, which would you choose? And two-thirds of the people chose$50 ,000, so three times less, because it's all about that social comparison. And you have an assumption that if I'm in an environment where I'm making more than everybody else, then I don't have to spend as much because everybody's having to deal with that.

1:14:09So at the end of the day, what that comes back to is like, okay, well then how are you spending your money? And how are you spending your time? Because there's so many things in life that are so beautiful. Kevin Kelly, who I mentioned earlier. He sat in that chair. He did. Yeah, I love him. We have known him forever. He says, you know, money will make you rich, but time will make you wealthy. He said something like that. It's one of his maxims. And I think there's a lot of truth to that. So learning how to move from financial affluence to time affluence is absolutely one of the things that I think is very relevant to the second half of someone's adult life.

1:14:52Because, man, the first half of our adult life, we've got spinning plates. There are so many things happening at once. And Brené Brown calls it the midlife reckoning. No, she calls it the midlife, what does she call it? She calls it the midlife unraveling. I call it the midlife reckoning. I call it the midlife reckoning ball because you have to do a reckoning. But she talks about unraveling. And so much of that is learning how to say like, okay, what am I, how am I going to spend my time differently? Sure. And again, the memento mori is part of the philosophy on that. That's the most powerful idea from the Stokes is that people are very protective of their money.

1:15:31They're very protective of their property. If your neighbor started encroaching on your land, you'd be like, how dare you? I'm hiring a lawyer. And yet we waste the one thing that they're not making any more of, which is our time. And I think you realize as you get older, you go, hey, I'm the number one in my field or I've run this empire. I've done all this. And then you go, but how much of my time is my own? Right? You go, I'm on planes constantly. I'm gone constantly. I'm in meetings constantly. You pull up your calendar and it's all blocked off, you know, and it's not blocked off for piano recitals or family vacations.

1:16:14It's blocked out for meetings. And ironically, the more successful you are, the more meetings and work you have just to maintain that stuff. Right. And so I think. Guilty as charged. Yeah. You're just having to go, hey, like, I don't know how much time I have left. Yeah. And also, what was the point of doing all of that if it doesn't result in autonomy, connection, happiness, all these things that are ultimately, you know, what we would truly define as wealthy. A very rich person who is unhappy, isolated, lonely, et cetera, we wouldn't – we don't want that. That first summer of COVID, I was in Baja and our MEA campus, of course, had to close.

1:17:01So I was doing so much Zooming and I was like so tired of it. And I decided to do something that now that I'm talking about it, I say, I should do that again because my schedule is very packed. Three times a week, between 2 and 5 p.m. in the afternoon, I put something in my calendar Monday, Wednesday, Friday called Spying on the Divine. And I would go out for a walk each time in a different location with my dog, Jamie. And we would go into nature. Yeah. And the whole premise was before I actually went on the walk, I would say, nature, what do you have to teach me today? Oh, that's beautiful. And the only way I had the time to do that was because I had these blocks of time in my calendar in advance and everything had to fit around them.

1:17:45Yeah. Because what happens in our life is we tend to actually say, okay, the stuff that's important in life has to fit around the stuff that's obligatory. Yeah. And, you know, it's a small shift. And yes, it's hard for those of us who have like so much going on. Like there's like, how am I going to find the time nine hours a week in this case? Well, again, it goes back to the editing process, the great midlife edit. Well, yeah, Seneca's point is that philosophy should not get the leftover you. work like substance you know the the obligations of being a human in western society that should get the leftover after you have checked off these things which goes to what you've written and talked about with maslow right yeah it's like you you've got to you've got to check these big boxes first and then actually the fact that there's a constrained amount of of working hours that's you'll you'll you'll have better meetings you'll be more disciplined with your work.

1:18:46You'll make the decisions faster. You'll be bringing a better self to those things as opposed to you let work be this boundary-less, all-consuming thing. And then you go, sometimes when I'm not exhausted for five minutes before bed, I spend a little time with the journal. That's such a bad way to do it. We did an exercise last year at MEA with our senior leadership team, about 15, 16 of us, because we needed boundaries. It was very clear. Like Like everything was, people felt overwhelmed. So we said, here's what we're going to start the year with. This is 2022. You're going to talk to your boss.

1:19:21You're going to make a list of your boundaries. Like what are the elements that define your boundaries this year? You're going to go over that list with your boss to make sure you guys are aligned. And then you're going to keep track of how you're doing on your boundaries. And once a quarter, we as a group, we'll do the thing I talked about earlier, the wisdom thing. But we'll also do boundaries and say, like, how would you grade yourself green, yellow, or red when it comes to how you set your boundaries this year? And then at year end, if you've made – if you actually feel like at year end you've gotten to a green over the course of the year, we'll give you a bonus equal to 5 % of your salary.

1:20:02So we basically were giving a boundary bonus, which is really unusual. I mean, like, this is like sort of how companies are – You wouldn't have done this for your hotel chain. This is a privileged later in life. This is a wisdom thing. This is one of the things. Like, okay, so we can say all we want about boundaries. But if we're not actually financially rewarding people for that, there's a lot of words here. Now, we didn't do it this year, partly because I think we sort of felt like, okay, we've now built a muscle. Yeah. And so let's use that muscle. You're on track. So that's a great thing for a company or a leadership team to consider.

1:20:39it doesn't have to be 5%, it could be 1%, it could be 10%, whatever it is. But it was a way of helping people to sort of say, okay, let's make this real and tangible. You want to go check out some books? Yeah. All right, let's do it. Let's do it.

1:20:59Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.

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