The Daily Stoic - Chip Conley on Finding Contentment and Embracing Our Achievements
Episode Date: January 17, 2024On this episode of the Daily Stoic Podcast, Ryan talks with successful hospitality entrepreneur and bestselling author Chip Conley on boutique hotels and stimulating the 5 senses, the importa...nce of reflection, understanding what the ego is telling you but not identifying with it, the most powerful idea from the Stoics, along with his New York Times bestselling book Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age.Chip Conley is on a mission to reframe our relationship with aging. As the founder of MEA, the world's first midlife wisdom school with regenerative communities, Conley is disrupting both the idea of higher education and senior living. He has both a BA and MBA from Stanford University and an Honorary PhD in Psychology from Saybrook University. He’s been a TED speaker at the prestigious annual conference multiple times.☎️ X and IG: @ChipConley✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Welcome 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.
Hey, it's Ryan. Welcome to another episode of the Daily Stoke Podcast.
I have a weird habit.
Maybe you pick 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 Ravling is in his late 80s,
is someone I talked to on a very regular basis.
You might have noticed a guy named Judge Frederick Block,
who blurbed the obstacles 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. I didn't know, like I didn't have a term for what
they were in my life until I met today's guest. Chip Cony calls them elders, specifically he calls them modern elders, right?
Like people who, and that's the role that Chip Connelly 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 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.
It 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 gotta 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 and honorary PhD
from Saber University. He'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.
You talked about, generally we talked about ego,
we talked about elders, we talked about influences,
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.
And 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 an overall great and super nice
guy.
I think you're really going to like this interview.
Thanks to Chip for coming out.
Enjoy.
this interview. Thanks to Chip for coming out. Enjoy. I remember very specifically, I rented an Airbnb in Santa Barbara. I was driving from San
Francisco to Los Angeles. I just sold my first book and I'd been working on it and I just
needed a break, I needed to get away and I needed to have some quiet time to write.
And that was one of the first Airbnb's I ever started with. And then when the book came out and did well, I bought my first house. I would
rent that house out during South by Southwest and F1 and other events in Austin. Maybe you've been
in a similar place. You stayed in an Airbnb and you thought yourself this actually seems pretty
doable. Maybe my place could be an Airbnb. You could rent a spare bedroom, you could rent your
whole place when you're away. Maybe you're planning a ski getaway this winter or
you're planning on going somewhere warmer while you're away, you could Airbnb
your home and make some extra money towards the trip. Whether you use the extra
money to cover some bills or for something a little more fun, your home could be
worth more than you think. Find out how much at Airbnb.ca slash host.
C.A. Slash host.
We 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 in 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 carry potter
Sure two stories sort of like you know like Carrie Potter. Sure. 100,000 books. Wow. Yeah. No. Where are you getting a hundred thousand books?
Oh, that's well, thank God we have a lot of alumni. We have a 4,000 alumni.
And so people aren't 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. Oh. And they sell,
they do a lot of stuff for like film studios.
Oh, that's what I've heard about that.
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 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,
what do they, like you know what drugs,
like they cut them with like a piece of that.
That a lot of them are cut with like cookbooks
or like things that are big big but no one would read.
So you kind of, and then psychopedia, but that 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, it's always cool when people find like weird niches that they can
go like big businesses out of, 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. You were meant to be a boutico tell designer.
Yeah, I bet hotels are a bunch of different things.
Oh my gosh.
Hotels, boutico, especially boutico tells, are very much about what does it feel like?
Not so much what does it look like?
I don't feel like.
And the feeling has looked involved 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 majority of guests
are never going to open the magazine, but as they pass
by the coffee table, what is it evoking for them?
They're just seeing it is the thing.
There's not only, they're not seeing it,
but they're also feeling that 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, if you've ever been to Ford's theater in Washington,
you go to the theater and then there's a museum next to it.
And they have this spiral column that goes from Florida ceiling made up of books about Lincoln.
And I was like, that is the coolest thing I've ever seen. And I wanted to do like when we're
designing the books or one of the things I was thinking of is like, 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 in front of while you're there?
You've already made the trip.
You've already made the trip, but then how are you documenting or sharing that experience?
There needed to be some sort of central focal point.
The more aesthetically pleasing and interesting that was was the more photos there would be, etc.
And so that's why we built that booktower.
And if you started to take them out.
These are all, so in there, a lot of them are glued and screwed in.
Okay, I got it.
Actually, this kid, he was like my neighbor where we live out in the country.
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 was 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
on the fireplace, the big issue was the weight.
Because these are both old buildings, but once you're 20 feet tall of something,
of hundreds of things, it 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 a full book.
Just a limited life.
Yeah, 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.
So we, but here it wasn't as important
because this is only like 10 feet or whatever.
But they don't come out.
Yeah, they're all screwed in there.
A lot of work.
Or glued.
Yeah, it's like, but it's just, you know, I mean, They don't come out. They're all screwed in there. 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 over here.
Like, 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.
Yeah.
Because my library, my office is a library.
And it is, it all three of the four sides have books.
So yeah.
Yeah, the only reason I didn't do it over there is,
so this wall was already covered when we put this in.
Like, so this was a barber shop.
The other one was like a harness shop,
one something else.
This was the one we did most recently,
but that brick wall, I had plaster on it,
but there wasn't anything built in front of it.
I felt, I don't know about you, but I felt weird covering up exposed brick.
Yeah, yeah.
And it's so nice.
No, I didn't want to.
I go.
So we didn't go all the way around for only for that reason.
Okay.
All right.
Well, we have a course too.
We are both sort of into our book.
So of course, but a surprise.
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?
Yeah.
So these are not books that you...
I mean, I wouldn't ruin hundreds of 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.
I mean, I have a question of like, I mean,
somebody's books you have multiple copies.
Yeah.
So that's true too.
So.
Yeah.
Although actually, I do remember when we were unloading them
from the truck, they had to stop me because I would see
but I was like, oh, I want to read that.
I was taking books out of that thing, which I have
subsequently read.
But yeah, this is it.
Well, welcome.
Thank you.
I thought we would start your term a modern elder.
Let's start with a definition there.
Yep.
What does it mean?
And we're already rolling.
We were already rolling.
OK, good.
So the origin of the term modern elder
came from when I was at Airbnb.
So I was a boutique hotel here for 24 years.
Starged one of you became, you know,
the second largest boutique hotel in the US.
52 hotels around California.
And then I had what it's commonly called
a midlife crisis in my 45 to 50 period.
We'll go back to that.
And then I ended up at Airbnb.
And within the first at house 52 at the time,
and the average age in the company was 26, the founders asked me to come in and be there in house mentor.
And about, they saw the role as that specifically.
It wasn't like, hey, we're going to hire you because you're an expert.
And then that's exactly what happened.
They hired me for my knowledge.
You know about hospitality, you know about entrepreneurship, you know about, you know, leadership.
But about a month or two into it, they said like 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.
And when I heard that, the alchemy of curiosity and wisdom, I realized like, 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, 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, I never worked in a tech company before.
And so I had to learn.
Right, been a while since you had a job.
Yeah, well, I had definitely been a long time
since I had a boss as well.
That's right.
So I was mentoring Brian Cheskey, the CEO and co-founder
while he was my boss.
Sure.
I was ahead of Global Hospitality and Strategy.
So what's it like to have your boss,
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 been that elder role.
What do you feel like modern is modifying?
Well, I think there's a couple of things.
Number one is, modern is modifying the idea that you're not just a wisdom dispenser,
you're a wisdom seeker.
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 to add 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. And reverence is what we have historically spoken
about, especially in American culture, you have reverier elders. That idea has sort of fallen
by the wayside. And that's a whole other story
we can talk about if you want. But the idea that you didn't earn the idea of being
an elder by just getting older, you had to be not just revered, but you had to be
relevant and being relevant required you to be curious.
And modernism, just, oh, I have 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 made, you know, an eight hour day, a made can clean
14 rooms.
Yeah.
Like that wasn't very relevant.
Sure.
And within the context of Airbnb.
So if I was sort of the old school, I don't know, I called an elder, but just the old school
hotel, hotel you, right.
I would have come in and just said, like, here's how you do things.
Yeah.
But I actually had to sort of say, okay, I'm curious.
I'm going to start by actually being the intern.
Right. 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, you
know, when I was a, you know, 24-year-long CEO of my own company, yeah, I didn't necessarily
learn humility. But I learned humility in my fifties in a way that I really appreciated. Yeah, and I wondered how much modern is also just saying like, I'm not old.
You know what I mean?
Like it's a shoulder implies old, but modern elder implies something different, and we don't
nobody wants to be seen as well.
Don't we like juxtaposition?
I mean, it makes it more interesting.
And so modern elder speaks to both the ageal 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 the worldwide, the longevity's skyrocketing
at post-COVID still.
And so we are gonna 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 and there's a Sennaq Align. He says we learn as we teach. Yeah. And the idea of this sort of
you're getting as much as you're giving. And if you see it as this two-way street,
then you get better and they get better.
The problem, I think, is if you feel like your wisdom
entitles you to teach, but you're not open to learning.
And I think the best mentor, mentee, relationships,
it's the more experienced person is explaining
all their experience.
And then the younger person is bringing their energy,
their sense of what's popular and new,
their curiosity, their fluency with things
that are recent exactly right.
That's exactly right.
Well, for me and Brian Chesky at Airbnb,
it was an EQ for DQ
Exchange and Brian had the DQ not Derek Queen although frankly out here in
You've got a Derek Queen. I'm sure
But not DQ as as in digital intelligence. I
Didn't have digital intelligence. It's 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.
So I learned a lot from him.
He learned emotional intelligence, broadly speaking, around leadership, around culture, around strategy. I mean, strategy was less
the leader, emotional intelligence, but so there's a lot we learned from each other. And I think that's
really the ideal kind of relationship. You know, the Ryan by the year 2025, the US Department of
Labor, by 2025, the US Department of Labor says that the majority of Americans are going to have a younger boss.
Now, we've never seen this before.
Right now, it's about 45%.
So, 45% of Americans have a boss that's younger than them.
Now, most didn't have a boss that was 21 years younger than them.
Like I did here.
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, 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 okay boomer.
Yeah.
Because that okay 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. You know,
when the person thinks they know and they don't know, or they think they know and they're
because of that arrogance, they don't know that you already know. Right. Yeah, or there's just a
cure, the lack of curiosity. Yeah. 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.
So 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, Senna could 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 sure he says we just waste a lot of it. Yeah. And
I think that's very true. And so what we can especially learn
to do with growth mindset in mid life is to say, okay, I learned
how to surf at 57 because of that question of like, okay, at 67,
it's going to 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 XY or Z, right?
And 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 event like the idea of going, hey, I've been down that road. I know what's
there. And you're going to part of it. You're going to have to learn by experience, but
hopefully my experience will help you recognize what you're experiencing have to learn by experience, but hopefully my experience will help you recognize
what you're experiencing sooner and it can it can just shave some of that painful trial and error out of it. A great mentor is a wisdom accelerant. And so that and that's what we all need in life is
you know to I've been doing something since age 28 and who knew I was going to be doing that and
you know many years later having a midlife wisdom school. At age 28 I had 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
Yeah, age 28 I had been running my boutique hotel company for two years
We had the Loma Prieta earthquake in 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
See, yeah, who didn't know what to do when I was running out of cash.
So one day, a friend of mine said, hey, you know, 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 an engineer journal.
But 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,
like, said all kinds of terrible things about it, my lesson to myself is, why don't I go
to the critics before I present it to the whole group to get their finger prints on it.
And so like, okay, let's try that. And it worked. But at 28, that sound, I mean, at 63 now, I get it.
But 28, I didn't know that.
And so what I do is I make a bullet points
of the key lessons of the week,
and then how it will serve me in the future.
Sure.
And.
What journaling does it allow you to see patterns?
It 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 Jouada Viva,
my boutique hotel company at Airbnb and now at MIA Modern
Ultra Academy, where once a quarter we sit down as a team
and we say what was our each of our biggest lessons of the quarter
and how will it serve us moving forward? Number one, number two is what was our of our biggest lessons of the quarter, and how will it serve us moving forward?
Number 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 an knowledge economy,
because in an era of AI, where knowledge is...
Facts, figures, info is gonna be a commodity.
Yeah, sure.
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, but 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.
And what part of my life?
You know, obviously I just mentioned surfing in Spanish, but let me say even more integrally.
I wish I'd had children earlier.
I had a foster son.
When I was 28, I became a foster son to a 13 year old African American kid
in San Francisco, who my first hotel was in the 10 year line San Francisco. He was a, he ended up
being a group youth home and I was mentoring him. 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
upbringing. And I'm still in his life and it his life, but it's been a hard road.
I'm gay and so I was like, okay, how am I going to have kids?
Well, I'm now 63 and I've got kids who are soon to be 13 and 10.
I'm sorry, 12 and 9.
I'm doing my math ahead because they both have birthdays in the next week, next month.
Bottom line is, I wish I'd had biological kids earlier. I had them with a lesbian couple in Houston.
So that's part of the reason I come to Austin and Houston a lot.
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 one is more time and that actually is coming
So that's the good news
I'm 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 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, as someone who came out at age 22,
I sort of immediately thought, like, I'm not gonna have kids.
Right.
And we now live in...
Because, it's a society that wasn't as accessible or...
That's right, that's right.
So now we live in a mirror where it's like very accessible and more accepted.
And yeah, so I would say that's probably one of my biggest regrets.
I can't do a do over on that one.
No, and I think about the two.
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 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 a sense of what matters, you know?
For sure.
That you can't help but think,
what would it have done to me to,
what would have done for me to have learned
with these things earlier?
Maybe you couldn't have, maybe you would have,
not learned the lesson to later,
but you see how much it transforms you as a human being
and you go, why did I wait as the old me?
You know, yeah, it definitely forces patients.
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, absences or the opposite 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, but it's the other kind of presence, right?
It's actually being there.
So it's like,
when you're with your kids, be with your kids, right?
And how much uninterrupted time
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. Yeah 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 says 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 a military actually setting up
a train track for his grandson.
And Churchill's just sort of watching him,
and the guy's like, what's he doing?
And Churchill sets up the whole track.
Then Churchill gets down and he goes, put a train on it.
And he's like, okay, 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.
And 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,
like where you play Legos or jump in the pool
or you do just crazy kid stuff.
And it's a...
Well, he was Play-Doh said you could learn
a lot more about a person from like an hour of play
than from a year of conversation.
Sure.
And I think that's true.
I mean, that's one I actually, that's interesting segue.
That is one of the number one things I've learned from teaching at a midlife wisdom
school.
It 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
Yeah, 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 do to
become a newbie again and
That allows you to become a newbie again. 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 when you have we don't have fresh new
experiences, life starts to actually feel like it's accelerating. And 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 gotten really, 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 you haven't tried before.
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Yeah, I think if you asked kids
like what's the defining feature of being an adult, right?
They might tell you something like,
you don't have to learn anymore, 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, right?
And so there is this sense that education is this thing
you have to do when you're young.
And then thankfully, mercifully, it ends,
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 Mark Serelyas is,
you know, he's the Emperor of Rome,
he'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 sex as 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 is like when was the last time you learned something new when it was the last time you were a beginner when is 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
I'm gonna have to do so much reading and learning just to figure out what is here like where where I have to like
What is here, 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 not do it,
and then it's easier if you are gonna 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?
And people head for the bar pretty quickly.
Because that's a deep question.
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 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. I love meditation.
I've been doing meditation for 40 years. I was on the board at Esselin. That's where I learned
yoga. I'm sorry, you 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 lumber.
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 I 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 and 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 do is 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 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.
But 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 you're 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 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 way,
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 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.
And you're used to only being in rooms
that you're invited to be in, right?
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 in stuff is, is you go like,
you know, usually I would be at the head of this room or class. And actually now I'm the humble student.
Nobody cares about me. Nobody will like to have to just flip the hierarchy or the status is really,
Flip the hierarchy or the status 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 Richard of course.
And he's an M.E.A student.
He came to M.E.A. 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. He and Carl Jung have both said
that the first half of our adulthood, it's the primary operating system is our ego for
all kinds of reasons. And it's around mid life 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 biology may vary, you know, I'll never forget, so I already tell the audience here,
the story of what I met Ryan, it was at Summit and Ryan.
Talked with the mountain, right?
Yeah, talk the mountain. I think so. And then, and it was four or five years ago.
And Ryan was there as was Kevin Kelly. And Kevin Kelly got up and gave us talk about technology.
And he's in his mid to late 60s.
And then Ryan gets up and talks about wisdom and philosophy.
So 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 me thinking back to this idea of,
you know, 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,
learning that you're supposed to actually let go
of your ego doesn't mean you actually get rid of it. I of it like a dance so in sixth grade I went to bottom dancing and
Went to bottom dancing school and was more like learning masculine and feminine roles and more than anything
But you learn the techniques and things and so yeah the boys leading the girls following
And that's sort of what the ego and the soul have done in the early part of her adulthood
And it is around 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 sociologist 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.
It's not that it gets 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.
And to me, it's like I have a temper.
But I don't have to make decisions out of anger.
Like I can recognize why I'm feeling what I'm feeling.
That's what you learn in meditation.
That's 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.
And 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 gonna take a breath
and I'm gonna say, actually, I don't want my ego
to be in charge here or to lead here.
I'm gonna step back and let a different part of myself,
I'm gonna open up a different part of myself.
I'm not gonna let ego come between me and this potential lesson or this potential connection.
I'm not going to let ego drive me into this, you know, cliff or off this cliff, right?
And 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.
You know, Victor Frankl, who
man searched for meetings one of my favorite books. He wrote between stimulus and of course,
in a concentration camp, it's easy to be reactive. Sure. But he wrote between stimulus and response,
there is a space. Yeah. 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. Because
often it's not stimulus and response, it's stimulus and reaction. And the soul doesn't react.
The soul responds.
The ego reacts.
And so learning how to create that space.
And there's the language for in social science about emotional moderation,
something that actually does tend to get better with age.
So these are things that we can learn, but we can train them.
Like that's the part that's like part that's what we have to learn.
It's not just a matter of having it happen, just like wisdom can be accelerated.
So can EQ your emotional intelligence.
You also have, as you get older, you have a larger and larger body of evidence.
That's right.
So you go, you can really see whether something is working for you or not.
Yeah.
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 done, basically zero. And so you can go, hey, I know more about myself and I have,
I've tried it this way, I've tried it this way, I've tried it this way without fail for 25 years
and it's not gotten me any closer to where I want to be.
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.
You 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 Eldritch Academy,
M.A. 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 called 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 the hero's journey, that you can see your
patterns. So one of my patterns is,
I have a very long, I have a lot of patients generally, with people. I have a very long fuse,
but then it gets to a place where it's like, it just like, no more. And so I get to a place of resentment. 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 that I get, that 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.
I 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 wanna go far,
if you wanna go fast, go alone,
if you wanna go to far, go together.
I am 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 feel like a 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?
How does something come through me?
And how do I create the channel
for something to come through me?
And then I was 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, what are the,
when could it have gone different?
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?
Because those are the early warning signs.
And 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,
as far as the reason I love reading Marcos Arelias
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 unhealthiness of that position, even, right?
One person shouldn't have that much power.
And then 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, we can imagine. He would, Mark Zuerus would famously bring his journals
and his books to the Coliseum.
Like he had no interest in the gladiatorial games,
but he was forced to go.
And he would be, 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.
No 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 know, you might know flow as the language
you would use for it, but like, is it journaling?
Is it gardening?
Is it cooking?
Could be writing your bike.
It could be working out, walking with your dog in nature
for one of my co-founders at...
It would work, right?
I mean, it's surfing.
Yeah, sure. But he never thought of it that way.
He thought, OK, mindfulness is meditation.
It's yoga, and 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 I, Dacker Kelton, who's on our faculty, amazing guy, greater 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.
Number one and number two on the list were pro-social human-centric things.
Number one on the list was moral beauty.
You felt awe because you saw courage, kindness, temperance, many stoic qualities.
You saw the best in human nature.
Sure.
And number two on the list was collective effervescence.
When your sense of egosepiration dissolves and your sense of common joy emerges.
And so what Dacker helped me to see with MIA with our Modern Ultra Academy was like,
oh, we are doing that every week.
Every week we have cohort of 24 people coming together in Baja and now in Santa Fe.
And they're feeling a lot of moral beauty and clueless of effervescence.
And they're realizing like, wow, my form of mindfulness might even have other people
involved in it.
And that wouldn't, that'd 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.
Yeah.
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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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,
an enormous company, and then you've,
I'm sure met a lot of extremely wealthy people,
met a lot of people who are not wealthy.
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 lifelong relationship with money.
So you're like in a relationship.
So what if you went to relationship counseling with money?
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 Lin Twist,
who wrote the Soul of Money, she's in 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.
So 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.
And I had a money script.
And mine was sort of like, money is sort of dirty.
But 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
so I during that time, it was not like, I want to be as rich as possible.
I 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.
And so you want to have stuff that people...
Didn't want to have 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 a lot.
You wanted people to admire the empire that you've had.
That's correct.
That's correct.
And so for me, money was the... it 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.
So when I sold, you ought to be, 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's like, okay, I did fine, but it wasn't like, I was, you know, I was going
to be set for the rest of my life. I still owned a bunch of hotels with that 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 the vest and six months,
and 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.
Like, I'm gonna 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 like care.
Yeah.
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 guy 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, a modern ultra academy, to I don't pay myself. And I just, you know, I don't
have investors at this point. I 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.
I was going through my own challenges during that time as well.
I just had this strong feeling in my get when I finished my full-time work at Airbnb.
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, and 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 you can't keep using the old assumptions
that you had about yourself
as where your purpose and your meaning
and all this stuff was
because now the world is different
and you are different.
Well, you may be, you may be, you've been living out somebody else's success script, your
parent's success script or whomever's.
And so it's that opportunity, you know, 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 of the thing they're going to live to is 90.
54 is exactly halfway between 18 and 90.
So 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-mory piece of being 54
and seeing your parents pass away, seeing friends pass away, having health issues
that come up.
That momentum worry helps people at Laura Carsonson 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.
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 gonna do this,
I have to do it.
Yeah.
So to be able to actually have that
momentum, more a perspective of like
season day, be in the moment,
while also seeing that, you know,
science is helping us to live longer,
is beautiful because you have this because it's a bit of cognitive
dissonance, but it actually works because there's a part of you that says, I'm going to focus
on the moment.
At the same time, I'm going to live a long time.
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 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-year-long 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 a moment, but also realizing you have a lot more life
ahead of you than you thought you did.
Yeah, my friend, Seth Cambar, he did this cool study. This was like 10, 15 years ago, so I don't even know exactly how you do it today.
But back when people were writing blogs all the time, he had this, he created this thing
that indexed and 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 is more or less confirmed with academic studies later, but young people
tended to associate happiness with achievement.
I just got this new job, I just got a raise,
I just climbed Mt. Kilimanjaro, right?
And then older people, their feelings of happiness
were almost always associated with some form of contentment.
My kids are visiting, had this great Thanksgiving,
we watched the sunset.
And so I imagine that as you get older,
you part of what's happening there
is you did the achievement stuff.
And it felt nice, but you realize 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.
Yeah.
And you realize that you can't just do more and more and more and more and feel better.
No, 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 interesting there are decoration of independence
in the US, says the pursuit of happiness 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 JD Salinger who wrote the catcher on the right said a wrote happiness as 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 to come and call
you out of the, I like to think of joy as something that's inside and it's something that
emerges, you know, we say joy is bubbling up. Yeah. As if it's inside of you. It takes some time
to get to that place in your life where you know what actually brings the joy.
And to be able to, there's a term in social science called environmental mastery.
And it doesn't, has nothing to do with ecology.
It's the idea that you know the habitats in which you're going to flourish.
It's particularly focused on, they focus on an occupational kind of things, in terms of
like what kind of culture, company culture.
But it's true across everything.
Environmental mastery is something that gets better with age.
You know, and for you, I mean, again,
you're like, you're precocious,
you're ahead of your game.
But you knew, you didn't necessarily wanna 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. Yeah, or gives you that sense of joy is something that I think we develop over the course of time
If you read David Brooks's book the second mountain. Yeah, of course one we were talking about money earlier. I think
very rarely is the second mountain,
primarily financially motivated.
And so obviously I've had a business career
and then I've had this writing career.
And then as we were kind of,
when we were doing this book story,
it was actually very helpful for my wife
and I to sort of go, this is probably a terrible business.
And but that's not why we're doing it.
Right, of course.
We're doing it because success is gonna be measured here
in a sort of a wider set of criteria.
But you still can find yourself,
how are we sales today?
Obviously sales can't be zero for too long
where you go out of business
and you can't continue to do the thing.
It's not a charity.
But the decision to say, hey, there's a choice.
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.
And so I think as you get older, you have these options of where you're going to put the success, the power, influence, you know, relationship, all the things you built.
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. know what it is what the person wants it to be. But I do think that we move from ROI,
return an investment to ROI ripples of impact. 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 know, 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 our, the numbers
of our ages, but also juxtaposition, what we're doing. I 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, when you're an American apparently,
like, really?
Am I gonna be doing that the other thing that happens
It's kind of humbling is like and I'm sure this is pretty 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 out your conversation Airbnb may have dwarfed the things that you did previously, right? You have this, like, decoupling money from success and also your own role in it is really
humbling and 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.
Now, that's a great thing because now I can go spend
three years of my life on another book,
you 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.
I'm just going to do what interests me, and and I'm gonna understand that if you have a portfolio of things that you're pursuing
doing this thing over here and doing that, one of those things is gonna be really right and gonna 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're having a positive impact. And ideally, you become successful and you
like Casey Neissette 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. Right? His point was, was like, how do we do cool stuff to fund
the stuff that isn't going to fund itself? Right? And 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 when you're 22 years old, you're not
in a position to think about that when you're 23.
Yeah.
Because you don't have the safety net or the base that you've secured for yourself, that
now as you've gotten older and you've done this longer, it should for you up to take more risk 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 money is a challenging topic for so many people.
Because it's about keeping up with the Joneses.
There's this fascinating study where they asked people, if you could be 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 you know don't have to spend this much because the whole everybody's having to deal with that
So at the end of the day that what that comes back to is like okay, well then
How are you spending your money? Yeah, and how are spending your time? Because there's so many things in life that are so beautiful.
Kevin Kelly, who I mentioned earlier.
You're setting that chair.
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, you know,
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.
Because man, the first half of our adult life
we've got spinning plates.
There are so many things happening at once.
And, and Brennan Brown calls it the midlife, have our adult life, we've got spinning plates. There are so many things happening at once.
And Brennan 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 unrec- 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, 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.
They'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 anymore 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 to, 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.
And it's not blocked off for piano recitals or family vacations.
It'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...
Gilti has charged.
Yeah, you're just having to go, hey, like, I don't know how much time I have left.
And also, what was the point of doing all of that if it doesn't result in autonomy, connection, happiness, me, all these things that are ultimately,
you know, what we would truly define as wealthy. A very rich person who is unhappy,
isolated, lonely, etc. 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 and
So I was doing so much zooming and I was like so tired of it and
I
Decided to do something that I now that I'm talking about I should do that again because my schedule is very packed
Three times a week
Between two and five PM 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.
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, it'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.
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 just 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 gonna find the time,
nine hours a week in this case?
Well, again, it goes back to the...
I've actually noticed some stuff.
It's going back to the editing process,
the great middle-eye fetish.
Well, yes, Enica, Senica's point is that
philosophy should not get the leftover you.
You work, work. Like like substance, you know, 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?
It's like you've got to check these big boxes first first and then actually the fact that there's a constrained
amount of working hours, you'll have better meetings, you'll be more disciplined with your work,
you'll make the decisions faster, you'll be bringing a better self to those things.
Yeah.
As opposed to you let work be this boundary list, all consuming thing, and then you go sometimes
when I'm not exhausted for five minutes before bed,
I'd 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 everything was, people felt overwhelmed.
So we said, here's where we're going to start the year with.
This is 2022.
You're going to talk to your boss.
You're going to make a list of your boundaries.
What are the elements of 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 your 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.
So we basically were giving a boundary bonus,
which is really unusual.
I mean, like, this is like,
sort of how companies are,
is the opposite of that.
You lose a bonus for your hotel chain.
This is a privilege to do that 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 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. It doesn't have to be 5%, it a great thing for a company or a leadership team to consider.
It 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, OK,
let's make this real intangible.
You want to go check out some books?
Yeah.
All right, let's do it.
Let's do it.
Let's do it.
Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us
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