Good Life Project - Chip Conley: Ritual and Reinvention.

Episode Date: October 16, 2018

Rebel hospitality entrepreneur (http://www.chipconley.com/) and New York Times bestselling author, Chip Conley, founded and grew Joie de Vivre into the second largest boutique hotel brand in America.Twenty-four years in, he sold the company, leaving him to figure out what to do with the rest of his life, and the wisdom he'd accumulated. He was approached by the founders of Airbnb to help transform the company into the world’s leading hospitality brand as Airbnb’s Head of Global Hospitality and Strategy and now Strategic Advisor for Hospitality and Leadership.Along the way, he's immersed himself in global festival culture, launched the Modern Elder Academy (https://chipconley.com/modern-elder-academy) and written five books, including his new book, WISDOM@WORK: The Making of a Modern Elder (https://chipconley.com/wisdom-at-work). In today's conversation, we dive deep into this journey.------------Have you discovered your Sparketype yet? Take the Sparketype Assessment™ now. IT’S FREE (https://www.goodlifeproject.com/sparketypes/) and takes about 7-minutes to complete. At a minimum, it’ll open your eyes in a big way. It also just might change your life.Thank you to our super cool brand partners. If you like the show, please support them - they help make the podcast possible. Hosted on Acast. See acast.com/privacy for more information.

Here's a question for you. What do you think about when you hear the word elder? Well, if you're in your 20s and 30s, pretty safe bet, you get a vision of somebody who's kind of old, decrepit in the waning years of their life and not in a place where they're sort of at their prime and offering incredible things to the world. If you are in the middle years of your life, the word elder may kind of have an association with elderly, and it may be a source of fear, something that you're trying to and fighting like crazy to avoid. Well, my guest today, Chip Connolly, has written a book called Wisdom at Work, The Making of a Modern Elder, which is really a reclamation of the word elder

and the notion of what it means to be, to serve the role of an elder in society, in business, in work, and the incredible value. And here's the kind of fascinating thing about that. What is the age range that we think about when we think about this? Well, one of the things that I explore with Chip is the notion that we may be entering this phase of our lives way, way earlier than we thought. And the wisdom that folks in their 40s, 50s can bring to business, to work, to the world in a world that is increasingly fast-paced, distracted, hyper-focused on the small granular things, the wisdom and experience of decades on the planet,

pattern recognition, astonishing experience, the ability to get the bigger picture, the holistic gist of things is increasingly valued in this world. But also the mindset that comes from playing the role of what Chip described as a mentor, somebody with incredible amounts to offer, but also who comes from a place that is not driven by attachment to accomplishment and ego in the past, but curiosity is a critical thing in the conversation. This is a wide-ranging conversation. Chip was the founder of Joie de Vivre Hotels, a huge boutique hotel chain that he built,

grew for about 24 years and then sold before then taking on a strategic and advisory role at Airbnb where he has had a huge impact on a company where he is twice the age of the average age person in that business. We dive into all of this in today's conversation, really eye-opening. I learned a ton from it. I'm excited to share it with you. I'm Jonathan Fields, and this is Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping.

And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs or later required. Charge time and actual results will vary. Mayday, mayday. We've been compromised.

The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him, we need him.

Y'all need a pilot. Flight risk. So, it's funny, I was trying to figure out when we first met. It was a while back now. I think it's got to have been over a decade ago. I don't really remember the context. Me neither. Other than I always thought of you as a glowing guy.

Which is a funny thing. I mean, no one's ever said that to me, but people have said it in other ways to me. But the idea that you are someone who is not enlightened, but is aware enough about the importance of having something radiate inside of you to know that in a world that prizes what's external, that, you know, sometimes the greatest treasure is actually inside. And it's a matter of how do you allow it to radiate a little bit. Yeah. And we'll thank you for that. And I think we've both been on that same quest. Yeah.

Sometimes knowing it, sometimes being completely clueless to the fact that that's what's going on. I got, you know, this is, you know, I'm fine with this potentially being on air or not. So I had a book launch on Tuesday. I have a TED Talk tonight at TED headquarters. And last night I got a cancer diagnosis on nothing terrible, but a serious enough one that I'll probably have to start radiation on my prostate. So, you know, sometimes you have to actually take it all in and just realize that, you know, the process of digesting life requires enough space to really let it metabolize. And this new news I just got, starting a book tour that's a month and a half long

and then literally going straight into our modern elder academy opening to the public after a six-month beta period, I didn't prepare for this. The good news is nothing. I'm not, you know, prostate cancer doesn't go move quickly, especially when you're a little older. But it is like, okay, you know, digest this.

And the process of digesting life, if you're really doing it, is beautiful because it actually, what we know, you know, and Viktor Frankl taught us this a long time ago with his Man's Search for Meaning in a concentration camp is that, you know, sometimes it's when we're struggling with the thing that we didn't want to hear, didn't want to know, the bad news, the bad feeling. That's when the magic happens. It can happen. Yeah. It can happen. Yeah, I mean, and there's like the sort of modern overlay to that is this kind of fascinating field of inquiry around post-traumatic growth. Oh, I love that.

You know, I've never heard that expression. Yeah, it's not my term. It's sort of out of research that I've been exposed to over the last few years where, you know, the exploration is why do some people who go through a similarly deeply traumatic incident, awakening piece of news, why do some people, it destroys them. And some people, for some reason, it becomes a catalyst for,

yes, there's going to be pain and suffering, but somehow they emerge from that. And it becomes this experience of profound growth and an elevating experience at the end of the day, you know, like when they finally like move through it. And I'm fascinated by the difference there also. What are the characteristics? What are the, how do people, why do people experience it one way or the other? As you were saying that, I realized that my natural response, not my natural, my

habitual response would be to attain as opposed to attune meaning i would figure out how to get as damn resilient as i could be and understand this thing and we'll we'll whip cancer and then you know one of the things i guess i've learned as i've gotten older is the shifting from attain to attune there are some times in my life where you know the attainment mode is exactly the path i need to be on and then there's other times when the attunement mode my life where the attainment mode is exactly the path I need to be on. And then there's other times when the attunement mode is where the learning is going to happen. At age 56, I took up surfing. I'm now turning 58 next month.

Surfing, like yoga, is not an attained sport. It's an attuned sport. You really have to attune yourself with the waves. And what a beautiful way for me to realize that, frankly, you know, when sometimes the news that comes in, you just sort of like, it's not about becoming, you know, type A about it. It's actually sort of like, taking it in and saying, Okay, what am I going to do with this? So, yeah. And it's interesting, also, because you have in your background, for those who don't know Chip's background, Chip and I actually sat down, we filmed the conversation years ago, that we'll certainly link to here. part of 24, 25 years founding and building this incredible hotel chain that largely consumed your being, your waking being for two and a half decades. It did.

You know, it was called Joie de Vivre. It still is called Joie de Vivre. I sold it, but Joie de Vivre means joy of life. It was not exactly the most practical name in the world. A lot of people don't know how to spell it, what it means, or, you know, et cetera. But I loved that the mission statement of the company was also the name of the world. A lot of people don't know how to spell it, what it means or, you know, et cetera. But I loved that the mission statement of the company was also the name of the company. We were, we were in the business of, you know, creating joy, but it was all consuming. It really was. And a lot of entrepreneurs have a tendency to hitch their sense of self-esteem to the ups and downs of the roller coaster of their business.

And I was one of those people for sure. And we went through the dot-com bust. So we were a California company. So we had 52 boutique hotels. We were the second largest in the US after Kempton. And all of our hotels were in California. And we had a dot-com bust and then we had the Great Recession. And right toward the start of the Great Recession, I had a flatline experience where I had a broken ankle, a bacterial infection in my leg. And I was on a really strong antibiotic and giving a speech in St. Louis on crutches. So you're on stage. I'm on stage. I didn't go flatline while I was standing up on the crutches, thank God, because I would have fallen over.

It was right after the speech. I wasn't feeling well. I was feeling quite nauseous, signing books for my book Peak, How Great Companies Get Their Mojo from Maslow. So it's all about self-actualization and moving up the pyramid to self-actualization when in fact my physiological needs at the base of the pyramid were in serious trouble. And when the second woman came up and this was an African-American woman said, you look awfully white. And I didn't know what she meant. That's the last thing I remember hearing. And I went out for three minutes unconscious, and paramedics showed up quickly.

And as soon as they put heart monitors on me, I went flatline. And I did multiple times. So at age 47, I had to really get clear about what was important in my life. What is the good life according to Chip? And at that moment, I realized I really, 22 years into running the company I'd started and being the face of the company, I didn't want to do it anymore. And I felt like Frankl,

this sense of being handcuffed and going into a severe great recession that I knew was going to be punishing. And within two years, I'd sold the company at the bottom of the market. And it was financially okay, but not as good as it could have been. But it was like my life, I got it back. And so I really, the allure of entrepreneurship can be fascinating to people. And yet, it can feel like handcuffs as well.

Yeah. I mean, it's so interesting that you say that because I have spoken with, I've worked with, I've known, as I'm sure you have, so many people over the years who have left a job that they perceived as being handcuffs or, quote, golden handcuffs. Right. as being handcuffs or quote golden handcuffs. And they didn't want to work for someone else. They wanted the freedom to work for themselves only to largely recreate, even if the facts were different of the company that they founded and then created and grew

and then became successful externally, the sort of the fundamental constraints that were crippling them working for somebody else, they recreated in their own company and came a time where they hated showing up at work at the company that they built. You know, it's sort of like dating somebody and then you break up

and then you start dating someone else. It's like, oh, they're just like that last person. Well, maybe it's me. Yeah, we tend to create comfortable habitats for ourselves. And even in the comfort, we're full of all kinds of neuroses and challenging things. So I will say, and I really, once I knew I wanted to go, even though it happened, it was like I went from,

it was the light switch wasn't on a dimmer. It was just like on to off. Once I knew I wanted to move on, it wasn't hard for me. And I had two years to prepare for it. But my gosh, it was hard for everybody else. It was, you know, we all wear these identities. And so, and I think of them as like name tags. And we have these name tags that are stuck to our skin and pulling it off is painful.

And especially if you have hair on your chest, I do. And the bottom line is it was a really interesting process to see how everybody around me was having a hard time with me ending an identity that I had. And we do that all the time. And the part that's fascinating about midlife is, can I riff for a minute on this? Yeah, totally.

So we as society and communities have a great history of creating rites of passage and celebrations. When people are going through transitional times, think puberty and bat mitzvah, bar mitzvah, quinceanera, going from adolescence to adulthood, commencement ceremonies, graduating high school, maybe college, you're going to get married. So you'll have a wedding. You're going to have a baby. You'll have a bridal shower. You die, you have a funeral. But between bridal shower and funeral, there's nada. And the reason there's nothing is because the longevity in the United States in 1900 was 47 years old. And then it grew to 77 years old, a hundred years later. So between 1900 and 2000, we added three decades of life. So in 1900, midlife was 23 or 24. You know, that didn't, you didn't need anything of that. But by 1965,

we had created, or a psychologist had created, the term midlife crisis. That was 53 years ago, and we have done zero to create a rite of passage in midlife, which midlife is full of transitions. It's ending a career and doing something else, or a job, having a divorce, menopause. For so many kids leaving the home. Empty nester. Exactly. And we don't have anything. So this is part of the reason, as I was writing my new book, Wisdom at Work, The Making of a Modern Elder, I decided to create a modern elder academy.

It's the first midlife wisdom school in the world on three acres of beachfront in Mexico, in Baja, one hour north of Cabo San Lucas. because I think we need a place where people go and imagine how to mine their mastery of what they've experienced in life and then how do you repurpose that in some new way but being fully conscious of what it is you want to do so you don't just create the same habitat that you were actually trying to move away from. Yeah, I mean, it makes so much sense to me. You and I, I'm a couple years behind you, but we're in that similar window where we've

done a bunch of things. But yeah, there's this, and it's almost like we're trying to figure out where are we now, both in the narrative arc of our own lives, but also in the greater arc of where we fit in society in terms of contribution, relationship, all these different things. And it's funny, too. I think I'm like the last year of Gen X, and you're like the early years of boomers, right? Yeah, the late years of boomers. Yeah, so we're four or five years away. And Gen Xers were kind of like always commonly known as like, we just don't believe in anything.

We're just like, we just got sandwiched in the middle. Completely disillusioned. And plus you're a small generation, so no one talks about Gen Xers. It's all about millennials and boomers. There was like three years where it was all about Gen X and boom, done. So we're like forgotten. But it is interesting that as I have similar conversations with friends now, really trying to navigate like what is our place in the world? And as stuff happens to us and to friends of us, and we try and figure that out too.

And we also know that there's a lot of value that we can bring to all parts of our world and to all parts of our life. But there's also a lot of stuff we have to let go of. And I want to dive into that a lot more with you. You decided to start this place in Mexico. We talked a couple of years back. You were on this maniacal festival adventure. Is this a part? Was this sort of like an inquiry process for you?

So yeah, to sort of create the chronology, I sold my company. I had space in my life. I wrote a book called Emotional Equations and it came out in early 2012 and did really well. It was a New York Times bestseller. And it was really, frankly, in many ways, doing the catharsis of my past few years since that Flatline experience.

And then I sort of asked myself, okay, I have space. What do I want to do? And I had been at that point on the Burning Man, the art and crazy festival in Nevada on the board for a few years. And I was like, wow, what kind of festivals exist around the world? And I wasn't just looking at music festivals or transformational festivals. I want to go to religious pilgrimages and art and film festivals, et cetera. And there really wasn't anything. So I decided, okay, I would like to see if I could fancy myself to be the world's leading expert on festivals. And I spent a couple of years doing that.

One year in particular, I went to 36 festivals in 20 countries, including Maha Kumbh Mela, which is 100 million people at the Ganges River. The biggest collection of humanity happens every 12 years, the big one, and then the smaller ones with 20 to 50 million people happen every three years. What I was fascinated by was in a world that is full of urls websites why is it that festivals are blowing up and with the irl experience in real life experience and the more digital we get the more ritual we need so the idea of collective effervescence, which is a phrase that Emile Durkheim came up with

studying religious pilgrimages back in the early 20th century. I was fascinated by that. Still am. I still go to festivals occasionally. But, I started a company called Fest 300, which then merged with a company called

Everfest, which is the largest festival discovery site in the world. But along the way, soon after I started that Fest 300 site, I got a tap on the shoulder, so to speak, from Brian Chesky, who is the co-founder and CEO of Airbnb. And that's when I sort of said, okay, I'm going to try to do both these things, this festival thing and Airbnb. And that lasted about three months. And I was like, no, the Airbnb thing is like a full-time role as the in-house mentor to Brian. And then I became the head of global hospitality and strategy. Yeah, and I want to dive into that.

Before we leave the festival exploration behind, though, I mean, it sounds like, yes, on one level, it was for you a fascination with why is this happening in culture right now? But at the same time, I can't help also noticing that your immersion in festival culture and deep global travel happened at this sort of like crux move in your own personal life too. Yeah. It was a fascinating time. I was, you know, it's so interesting to look back at your life and to sort of see the, the journey you've been on and see the sort of almost like the, what's the, the common thread. And I think during that time, I was in a place where I really wanted to

explore like a child. And I didn't know festivals all that well. But I think more than anything, I was fascinated by humanity. You know, just the element of the need to... When collective effervescence kicks in, what happens is our sense of separation, the ego starts to evaporate. And what comes in its place is this communal sense of joy. And I think you had Radha on the show recently. Radha and I had a, on my book launch night, a couple nights ago, we had a talk at Story here in New York. And, you know, the idea of Radha Agarwal started Daybreaker. And so, again, that's a similar form of like, okay, how do we somehow move out of our identities and move into this place of communal joy?

And I'm fascinated by that, and I think I will continue to be. Of course, I started a company called J and I'm, I think I will continue to be, um, of course I started a company called Joie de Vivre when I was 26. So yeah, joy has been always a fascinating emotion for me. But, um, I think more than anything, I was maybe searching for some of my own joy having, you know, been a handcuff to my company for many years and, uh, really ready to sort of liberate myself from that. Yeah.

And I, it makes a lot of sense to me. In a way, it's almost like your immersion in the festival scene for a window of time was like a certain, in a way, a rite of passage for you. I think it was.

Or a series of rites of passage. It was. It also gave me a great sense that, and I talk about this a lot these days, that when you are curious and engaged, you sort of become a little bit timeless. I mean, we still have age moving in our lives, but I have a lot of people asking me today, since my new book is really about midlife and beyond in terms of the workplace. And people are just saying, well, I'm worried that people will see me as a 58-year-old. And it's like, well, truly, when you're actually in a place of curiosity and engagement, people lose track of your age. It's true.

And you may be full of wrinkles. You may have a bunch of scars of life on your physical body. But when you are in that state of engagement and curiosity, we are all in somewhat of a timeless space. And I think in the festival world, which in certain elements of the festival world, it's incredibly narcissistic and it's good. Everybody's showing lots of skin and not exactly the thing you want to do in your mid to later 50s. But the truth is that when people really see you for your energy, more than they see you for the physical existence, people start to realize, my God, I'm very drawn to you. And I'm not talking about necessarily romantically here,

but I'm talking about people are just drawn. So I would just say, whatever it is, you is, it doesn't have to be a collective environment. It could be literally taking photographs and photographs in the process of being a photographer, which is a very personal process. It can be. You could get into that engaged and curious state. It could be when you're writing. It could be running on the beach. It could be when you're writing, it could be running on the beach, it could be whatever it is. And I think the thing that's interesting about, I think the first half

of our life versus the second half is the first half of our life is about accumulating friends, stuff, relationships, children, potentially roles and identities. And the second half of our life is about editing. And that editing process of understanding, getting clear on what's important. Someone said to me once, you know, you're old enough to take up surfing, but young enough to know what's important. I'm sorry, you're young enough, the other way around, but I love the fact I got it wrong. You're young enough to take up surf, you're young enough to take take up surfing old enough to know it's important. And the fact I got it wrong suggests that it is all very fluent. I think there's something to that. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest

Apple Watch ever, making it even more comfortable on your wrist whether you're running, swimming, or sleeping. And it's the fastest charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to

previous generations, iPhone XS or later required, charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th.

Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him, we need him. Y'all need a pilot. Flight risk. The thing that's fascinating about longevity today is Mary Catherine Bateson, Margaret Mead's daughter, talked about the midlife atrium.

So we're all going to maybe have 10 or 20 years longer in life than maybe our parents or grandparents. And the question is, when in your life does that occur? A lot of people have sort of thought of, okay, that 10 to 20 years you get is at the end. So you're just decrepit longer. The actual truth is not the case. In fact, what you get is you get more midlife. You get a longer midlife. So this midlife crisis has become a marathon. It was 45 to 65. Now it's 35 because people feel irrelevant earlier to 75 because if you're going to live to 100, It was 45 to 65. Now it's 35 because people feel irrelevant earlier to 75, because if you're going to live to a hundred, you may work to 75. And all of that's interesting and maybe illuminating to realize, okay, I'm 57 years old. I did a longevity online calendar the

other day or test, which said, okay, how long are you going to live to? So I was going to live till age 98. Well, do the math. If I've, if you start counting at age 18, when I became an adult, I've had 39 years of adulthood. I have 41 years of adulthood ahead. I'm not even at halftime as an adult. And that kind of thinking helps open up this midlife atrium to imagine the air, the light, and the possibility flowing into a period of time that for many people, people think of it as a dark and scary time. Yeah. I wonder though if, and I completely agree with everything you said, I wonder if the reason so many people think of it as a dark and scary time. I mean, on the one hand, yes, I think a lot of people perceive themselves as being closer to the end, like mortality becomes realer. But on the other hand, I feel like it is a moment for so many people. And as you so profoundly observed, this moment is happening earlier and earlier. It's happening in the 30s for a lot of people now.

It's an awakening to the existential question. It's an awakening to the existential question. It's an awakening to the fact that, huh, so I'm waking up, I'm working my ass off, I'm putting my head on the pillow at night, every night, and I know I'm really busy, but I have no idea why I'm doing what I'm doing. It's not really filling me up. And I think that's a lot of where the, it is yes, an acknowledgement of getting closer to mortality, but also an awakening to the truth of the fact that most of us, you know, the way we contribute to the world is largely devoid of genuine purpose and expression. Yeah.

I think this is an area, I think we've learned from millennials and I'll come back to that in a moment, but I agree with this. The happiness curve is a great book. Jonathan Rauch book. I'm actually looking forward to hanging out with him in DC this Sunday. And the study, all I did was popularize something that was already out there, which is the U curve of happiness.

But it's a really good book because it actually helps us to understand what's going on in our forties that just sort of like kicks us on the butt. And across virtually all cultures in the world, 40s is your low point, you know, usually about 45, maybe 47. I had my flatline experience at 47. And then it gets better. People get happier in each decade after that, partly because they start getting clearer on what's important to them. The reason I think the millennials have something to teach us on this is that I think the fact that the iPhone was introduced in 2007, what hasn't been talked about a lot is the iPhone and the idea of mobile technology blended work and leisure in a way that wasn't quite there before. Yes,

people worked on weekends and they did stuff at night, but when you have a mobile piece of technology that you actually are walking around with and at nighttime or on the weekends, it goes off with a text or with some message. The fusing of work and life and leisure was more blended than work-life balance could ever define it in such a way that I think what it meant was people earlier in life realized, my work and my life, as Khalil Gibran said, work is love made visible.

And I want my work to be something that is purposeful for me. And so one of the things we can learn, and I think it's true of anybody in that 20s era, people, it was true of the hippies back in the baby boomer era that they wanted to do something that was meaningful. But I do think it's even more like grounded in the fact that the world is so blended today that if you think that you're just going to go have a job and leave your identity, personality, sense of purpose, and maybe even your values at the door while you do your eight to 10 hours, and then you go back and pick that up before you take the subway or the train or the car home. I don't think people younger are willing to live that way.

I actually think it may affect in positive ways that U-curve of happiness such that 40s are not this wake-up period of like, how the hell did I ever get here? Because people will be a little more conscious earlier in life about what they want to do. Plus, the idea of the three-stage life of you learn, then you earn, then you retire. The millennials look at that and say, why would anybody live their life that way? Whereas my generation, the boomers, that's the only way you had to live. And so it's like, okay, they take a gap year at age 32 or they retire

you know for do a sabbatical for six months and it's a very different way and I think it's a healthy way

I mean it's a really positive yeah I completely agree I think and I think I think corporate America is completely

like they can't understand how to actually deal with it like wait a minute we have to provide a place where we're not just creating industry and commerce, but we are serving an existential need. What? It's not about just adding a ping pong table.

Yeah. It's really interesting to sort of see, like to work with organizations and see that grappling going on. But I agree with you. I think at the end of the day, it's a really good thing. Yeah, I think so. I mean, I think we're moving, you know, there's my friend Gina Pell coined the term perennial. So, you know, it's not that we're necessarily generation identified, we're maybe identified as to whether we're in that perennial state. And what she means by perennial is Biparenual is someone who's naturally curious, always evolving in a place where they want to

be sort of timeless and ageless. And whether that's someone in their mid-20s or someone in their mid-70s, they can have actually sort of a common value system. And I think there may be some truth to that. I think we may see over time, especially with, gosh, we have five generations in the workplace now at the same time. And I know there are a lot of people at Airbnb where I was, and I was twice the age of the average employee. There are a lot of younger people there at Airbnb I absolutely identified more with than I did the handful of people my age in the company, which is there weren't many. But some of them really, my point of view with them was just very different. So I think, you know, I think more and more, it's not going to be, we're not gonna be so generation stratified and that would be a good thing. I mean, hopefully we won't all have to go live in sun city or some, some retirement leisure

world life. And, you know, a lot of people older in life now move back here to New York, to Manhattan, to New York City and say, empty nester, no Connecticut for me. I'm moving back into the city. And that's an interesting phenomena that didn't exist maybe 30 years ago. Yeah. No, I think it's really interesting. Let's fill in some of the gaps with, because we've referenced Airbnb a number of times now. So you, it comes a time where you meet Brian Chesky, one of the founders of Airbnb. Tell me about that. How does this all come together?

Well, what's bizarre, so I started my company Joie de Vivre when I was 26. Brian started Airbnb with his two founders when he was 26. And I was a pioneer as an early boutique hotelier, but by the time I was 52 when Brian reached me, I was no longer the pioneer. I was now the establishment. And when he approached me and said,

there's this Airbnb thing, I was like, really, people want to stay in each other's homes? Why? I didn't get it. So I was like, I clearly was no longer sort of the disruptive mindset. But I really appreciated Brian. I was sold on Brian.

Brian had this growth mindset to use a little bit of Carol Dweck's work. He really had a sense that he wanted to improve himself, not to just prove himself. And I was fascinated by that. I was also fascinated. He said, let's democratize hospitality. And yeah, part of the reason I got out of the hospitality business, sold the company was because more and more of the people who actually were investing in hotels were private equity firms. And nothing wrong with that. It's just that they were purely mercenary. Their interest in why they got into hospitality real estate was because the returns were higher.

Whereas a lot of people got involved in hospitality in the past because their families had been in it or they like the spirit of, you know, serving people. So the idea of like, you know, creating micro entrepreneurs around the world who were going to be home sharing was like, it was interesting. Obviously it was disruptive and controversial and all that. But at the time I joined, it wasn't so much, it wasn't well known. This was very early 2013. The company was about 1% of the size it is today, maybe 2% of the size it is today. So it was a really small company. And I ultimately said yes with the idea it was gonna be a part-time thing. And, you know, he tricked me being, you know, there's no such thing as part-time in a, in a startup. So this is me again, the habitat, I just ended up in the same habitat, but it was

now meaning working very hard and long hours, but I didn't mind it. And I, the thing I loved about it ultimately, Jonathan was, I was able to put some guardrails on it. I learned that. So because it wasn't my venture and it wasn't, you know, I wasn't the, I acted, I had that totally right size, my ego. I'd been the, you know, the little mini, mini, mini, mini version of Richard Branson at Virgin, of Chip at Joie de Vivre. I was the face of the company and et cetera, et cetera. And the idea of – I used to be the sage on the stage and now I was the guide on the side. And I was here to serve this company and these three young millennial co-founders who were 21 to 23 years younger than me.

And it allowed me to have guard rails. And ultimately, three years into it, I went to a part-time status. Four years into it, I went to a strategic advisor status, which is what I've been for the last year and a half, which basically means I give them 30 hours a month. And so it's been beautiful. It's been a beautiful way to also learn about what does it mean to be a modern elder who is as much an intern as they are a mentor. So, Deacon, let's dive into this idea of a modern elder. I mean, it's kind of funny that the term elder, if you asked me 20 years ago, I was like,

wow, I don't want that association. No, not at all. You asked me 10 years ago. The thing that flipped the switch for me was probably you brought up Branson. Yeah. And he tells the story of how he went and I think was actually asked by, how can I be totally spacing on the name of 27 Years in Captivity? Oh, Nelson Mandela.

Yeah, Mandela. Yeah. But essentially to, like they came together. It's because you're aging a little bit. It's too funny. You're aging a little bit. It's too funny. You're flipping a quote. I'm forgetting your name.

It's like, man, we're showing ourselves here. But I'm good with it. Me too. Yeah, the idea of, okay, so we're going to bring together this council of elders who are the wisest, some of the wisest people out there who have been through profound change, suffering, massive, massive accomplishment in different levels, geopolitical, business, cultural, societal, to offer wisdom and guidance without an expectation of remuneration

just because it was time to share. And I was like, huh. So they're really, they're kind of like reclaiming this thing. But still that was in the context. Most of the people who were part of that group were in that much later stage in life. That's right. The idea of creating an association decades earlier is interesting to me.

But also, I'm still not entirely settled with it. Yeah. Well, let's talk about it. Because I hear you. I mean, my publisher wasn't settled on it either. In fact, the book was originally supposed to be called Modern Elder. And now it's called Wisdom at Work, The Making of a Modern Elder, because they said, oh, it's like, let's not go with it too forward as the name. Well, first of all, I think an elder is someone

who is older than the people that they're surrounded by. And so you could be an elder in your early 40s if you're surrounded by people in their mid-20s. It means you have more experience. Maybe a little bit of judgment has, good judgment has been built up from your experience and from your skin, knee, or your broken toe, or whatever it is in life. And you can share that. So I think there's that.

So I think elder is really a relative term. And at Airbnb, if I joined at age 52, average age in the company was 26 and a half. So I was twice the age of everybody. And so I was definitely an elder. I didn't initially call myself that. It was when Joe Gebbia, one of the other co-founders, and I started spending a lot of time together and I sort of was becoming his, almost like his personal coach and just an advisor, just spending a lot of personal time with him. At some point, I just realized, I'm like a modern elder. And the difference between the traditional elder of the past is they were regarded with reverence.

And in some societies in Asia and in Latin America, still, there's a little bit of that, although the more digital we get, the less it is true. So that regarded with reverence is what I saw with traditional elder. But I think the modern elder is regarded for their relevance. And the relevance means that you better be as much of the curious soul as you are the wise elder, meaning you better be as focused on learning as you are on teaching.

And that's why I say, I joined Airbnb and a week into it, I realized, wow, I have all of this sort of old school bricks and mortar hospitality knowledge. And I was in a world that was full of tech lingo. I didn't understand what they were saying. So I realized I better become the curious beginner's mind in the room asking questions about technology. Now, if it was just asking a little silly word that I didn't understand, I had people

in the room who are my tech translators and they'd help me. But sometimes I actually pointed out a lot of blind spots that the company hadn't thought of because most people were focusing on optimizing and I was asking the big why and what if questions. And it was beautiful how all of a sudden the oldest person in the room was asking sometimes the most are the, at my age, almost 58, I'm sort of the new young old, meaning I'll spend the next 20 or 25 years to my early 80s in a very operationally active role in whatever I'm doing. I have no doubt about that. And who knows, maybe way beyond that. So I'm not old or elderly yet. And I think that we need to liberate the word elder from elderly. And I'm not saying that elderly is a bad word. But I think when we think of elderly, we think of someone who is actually

in a later stage of needing support and maybe not being able to sort of give back in that kind of legacy way. And so I think reclaiming a word is not unusual. The Yankees were the colonists and the Brits called them Yankees because they were the dandy Yankees. They sort of like intesting their masculinity. Being black in the South was a negative word until black is beautiful actually came out and Malcolm X started speaking about, we are black. And so that was a word that got reclaimed. Queer was a word that got reclaimed. And I think elder needs to be reclaimed because if we're going to live longer, and if we're going to be in the stage of life from our fifties to maybe, you know, eighties, there's a period of life where we have something

to offer. And if we don't, especially in a world where power is cascading to the young I think Travis at Uber might still have his job if he had a modern elder by his side to sort of just mellow him out and tell him, you know, dude you've got to mature your leadership behavior here because

you're running a big global company now so I do believe that there's a place in the world for the modern elder. And so, yeah, I'm out there trying to help us to reclaim that word. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series 10, available

for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg.

You know what the difference between me and you is? You're going to die. Don't shoot him, we need him. Y'all need a pilot. Flight risk. It's interesting too because I think language really does matter. Flight Risk. recently reflecting on the fact that we define that, and this was probably when I was in my mid-30s or something like that, and that was the mid-50s generation. And I'm thinking to myself, if you told, if you referred to me right now, or any of my friends as the silver sneakers generation, I would probably want, I'm a passive guy, but I'd probably want to clock you.

Well, how'd you like getting your AARP card at age 50? I mean, come on. Dude, wait. That's our rite of passage. Right, because we make so many, I mean, the language we use, I think, is so important because it comes along with these assumptions about capabilities

and how we treat people and how we choose to interact with them, the value. And when we step into that language, I think we either constrain or free ourselves to be a certain way in the value. And when we step into that language, I think we either constrain or free ourselves to be a certain way in the world. And when other people impose that language on us, or those titles, or those, all the assumptions come along with it. And so it's really interesting to hear about your experience at Airbnb, because it seems like it was unusually open. Like you had senior management and people in the company who were incredibly open to the

fact that, yes, the guy's twice our age and who cares? He's done some incredible things. He's curious, he's open-minded and there's astonishing value across the entire spectrum of age. And let's acknowledge that I was lucky. And that's, and writing this book, Wisdom at Work, The Making of a Modern Elder, I ended up interviewing about 150 other people who did not have my good positive situation that the founders of a company came looking for them. But I think what's interesting is that the young founders of Airbnb said, why is it when we think about diversity, we only think about gender and race and maybe LGBT issues, maybe disability issues. But we actually don't think about age. We don't think of age as a demographic where diversity is important. And what's fascinating is that the world is getting older,

and this is actually a very relevant demographic. So part of what I want to do is help to create almost a new generational compact where we realize with five generations in the workplace, there's a lot we can learn from each other. But I guess more than anything, the experience I've had has helped me to see that we have such an opportunity to recognize that the second half of life is not something that we should cringe about. The U-curve of happiness proves that. People get happier. But there's a word that I didn't know before I started writing this book, and it's called liminal. When you're in a liminal state, you're in a transitional state. And when you're

in puberty, you're in liminal. When you're in menopause, you're in liminal. What's interesting is that we have a tendency to think of midlife as not a liminal period. It's just the start of the decline. And in fact, I'd like to think of, you know, I hate to use a overused metaphor, but the butterfly was first a caterpillar. And if we were a caterpillar in our earlier years, and we seem to realize, and there's a lot of data that shows this, that maybe our middle years, maybe our 40s and our 50s are almost like a cocoon. It's the chrysalis. And then we come out the other side, not as this person in a wheelchair, not as this person who's having a hard time remembering things, not as this person who's sort of staring at, you know, the end of their life in three to five years. No, we actually come out the other side as a butterfly. And this butterfly is this

opportunity to realize we have, you know, our physical peak, maybe our twenties or financial peak, maybe around age 50 in terms of salary, but our emotional peak is later in life. We have developed pattern recognition around ourselves and others. And therefore there's a wisdom that has actually started to build up in us. And the question is, where do we share that wisdom? In the movie, the intern, Robert De Niro, with Anne Hathaway, he says basically, musicians don't retire. They quit when there's no more music left part of it was because the industrial revolution moved us from agriculture to, to brawn. I mean, being, you know, you didn't need to necessarily be an elder to be on the industrial assembly line, but on a farm, you really appreciated that farmer's almanac kind

of mindset that the 70 year old farmer had. And so, and then we go to technology era and even more so it's like, it's all about the young. So I'm not saying there's anything wrong with the young. I think the fact that you have brilliant technologists in their early twenties creating global giants before their 30th birthday is fascinating. And yet maybe they need to be paired with someone a little bit older, not because they necessarily need somebody to drive them because they're not, you know, driver's age yet to lead a company. But no, maybe it's because there's something that we can offer them. And that sort of emotional intelligence, good judgment, leadership, understanding,

and strategic thinking. I was supposed to be the head of global hospitality for Airbnb, which was a great thing. And three or four weeks into it, Brian said, you're now in charge of strategy too. I like the way your mind works. And it's like, okay, I've never worked for McKinsey or Bain or any kind of strategy firm, but he really liked the synthesis. One of the things that happens as we get older that's interesting is our recall, both recall and quickness goes away. It doesn't go away, but it actually diminishes some. But the thing that actually gets better as you get older in terms of your brain is all-wheel drive.

You're able to shift from left to right brain much more fluently. And what does that mean? It means that actually you get the gist of things. You're able to think systemically, holistically, and you're able to sort of see the forest and not get caught up in the trees. And frankly, young founders of companies get caught up in the trees all the time. And so part of what I had to do regularly in my sort of wisdom role was to help us to see, okay, where are we going? You know, what's the North Star? And to sort of see holistically, do we really see here? You know, as you get older, you start seeing your themes in

your life and you start seeing that thread and then applying that to young people in a way where they're hungry for it and you're not doing it. I like to say I was interning publicly and mentoring privately. So it's not about me sort of like being the highly regarded person. It was like having a private conversation with Brian on a Saturday. We did it all the time where I could point out some things about how he ran a meeting and could have done it differently. Or the just thinking of like, you know what, have you seen that we keep repeating something here as a company?

And that kind of thinking is what someone who's a little older could offer. And I mean, it makes a lot of sense. You're offering this in the context of business, but like, as you're speaking, you know, it becomes clear to me that this, this is about life. This is about this role across it's, it's about your willingness to move into, move through life and continuously re-examine your ego. For you, if you want to play that role of a mentor or an elder, you use the phrase mentor, which I think is a really interesting blend of, okay, so yes, there is a knowing that you have something to offer and simultaneously a knowing that you have a lot to learn. And to stand in that duality is not, it's a cute name.

It's fun to, it's a great notion. Right. But to actually operationalize that in your life and in your work every day can't necessarily be a real easy thing, especially if you have come out of a history of contribution where you did, you know, you're like, but I, but I accumulated all this.

I did all this. Like I got all these accolades. I built this thing. And then to sort of like stand back in that place where like, I'm showing up and sure I have something to offer, but man, I have something to learn from all of these others. Yeah. I, you know, Liz Gilbert's, Gilbert's TED Talk 2009 was so beautiful. And she talked about how hard it was to have such a success with Eat, Pray, Love, because how do you follow that up?

And if we tend to spend our lives trying to live up to something from the past without actually focusing on moving forward with the learning and the curiosity that is ahead of you, looking in your rearview mirror is not necessarily the best way to drive your life. There's certainly things to be learned from the past, but more often I think it's trying to look at that open road and have the sense of faith and just being in the moment of sort of seeing what's ahead. And I think that's been, you know, I like to meditate, and that helps me to sort of be in the moment throughout my day,

not just when I'm meditating. And I really appreciate the fact that as I've gotten older, I've really recognized that being present is one of the most unique and unusual qualities, especially in a distracted world where everybody has their iPhone out. And even the word presence is the opposite of absence. And absence is the way we live a lot of our lives. And we were living absence before we had the iPhone. But the iPhone took us even further in the direction of absence. And so I'm a real believer in the idea that as you get older, you start honing some emotional skills and some habits and presence,

learning how to actually inhabit what presence is. I gave a talk at the Summit Series guys thing in Utah last month. And, you know, I'm way older than most of the people there. And I was giving a talk on wisdom. And there was an owl out in front. And it was on someone's arm. And, you know, it was like a talk on wisdom and there was an owl out in front and it was on someone's arm and it was like a bird trainer. And so I asked the bird trainer, so why is the owl the wisest animal in the forest? Why does the owl embody wisdom? I'm about to go give a speech on wisdom, so tell me. And he says, it's because they're the best listener. There's no other animal in the forest that actually has a more attuned ability to listen. So that's a great metaphor for us to think about as how do we become a listener? Knowledge speaks and wisdom listens.

And to me, that premise that as we get older, we become more present with our listening and we are less distracted by all the other stuff in our brain and around the world that's calling for attention. But in that moment, we have that presence. I think it's more needed than ever. Mother Teresa talked about more than anything else, what we needed was just the sense of attention being paid to us. And I do believe that that is more necessary in a technological world than ever before.

Yeah, I totally agree with that. I think the more we're distracted, the success that we've had in our past, rather than how the things that we have done in our past have changed us as a human being. Yeah. And then what we now have to offer because of whatever success or failure we've had in our past. And if we stand in that latter thing as the basis of what we have to offer, rather than the accolades and the things we've built and done in the past, then I think it's a lot easier to let go of your ego and to let go of the fact like, I don't need to be recognized for what I've done.

Yeah. Because I know who it's made me in this place in my life. And that opens you to then listen and to be present, to be curious and to surrender and to take on the mentor sort of mindset and to not have to stand in this place of ego. Someone once said, the first half of your life is about being interesting and the second half of your in this place of ego. Someone once said, the first half of your life is about being interesting, and the second half of your life is about being interested. And I think that's the shift from the first half of the life is more about ego.

And let's be clear, when I say ego, I mean, ego's a good thing. It is something that creates a structure that helps you to understand who you are. It's a way to not be too overly merged with other people. It's what we do in, you know, in our early childhood to, to start to individuate from our, especially our mother, but our parents in general. Problem is that individuation process. And then the structure you build around that ego, the scaffolding around the ego that in off often is the thing that sort of is feeding you,

is you start believing that the scaffolding is the building or that the ego is the self. And when you get to your second half of your life, and especially if you've had a few major speed bumps along the way, you start to realize that there's something deeper than the ego. And it's that deeper, you know, movement from ego to soul that I think is often accompanied with midlife. And partly because I think maybe in midlife you start, the mysteries of life get a little bit more interesting.

You know, we're full of wonder as a kid. You know, the wonderful world of Disney and being wonder, like, oh, wow, why is the sky blue? And then we put our blinders on for about 30 or 40 years, and then we move into awe. And in the latter part of our life, awe is a word that becomes more interesting to us because it helps to show the magnitude of the world that we live in. At this Modern Elder Academy that we're doing in Mexico, I have Dr. Keltner coming. And he's, you know, like- Yeah, one of the leading researchers in awe.

He's one of the leading researchers in awe. He's now my neighbor down in Pescadero, down in Baja. And he's coming to do a week with us on, you know, midlife awe. And how do you, you know, reacquaint yourself with that sense of wonder and awe and, and how does awe help create presence and greater emotional wellbeing? So, you know, part of the fun thing about this Modern Elder Academy is literally, it's like, I get to invite some of the greatest people I know to come and do a week with me. So, yeah. That's amazing. So tell me more, because I was actually going to circle back to that,

because now I'm fascinated by this. Maybe you should come down and guess back a little bit. I know, I know. Tell me more about, I mean, what was the genesis, and what is it really about? Yeah, so back to what I was saying earlier, it was that the midlife is massively missing ritual, and it's missing rite of passage,

it's missing, there's so much transition that happens in midlife and it, most of it's silent, especially for men. And so as I was starting to write the book about 15, 16 months ago, I was down in Baja where I have a home. I just had one home, you know, right on the beach and it was a great place to write a book. And I was interviewing people and I was just so fascinated by the amount of anxiety and bewilderment I heard from people in midlife. And one day I just said out of the blue to some of my friends down there who live down in Baja,

which is in Mexico, Baja, California, Sur, Why don't we just create an academy here? And I started doing some research. There's nothing out there, nothing that's specific to midlife and has a curriculum. There's lots of great retreat centers. Bars and stuff like that. Omega and Esalen. I'm on the board of Esalen Institute and Big Sur.

But there was nothing that was specific to midlife and had a specific curriculum. And so the first half of 2018, we had 153 people go through one week and two week programs through the beta program, through the beta process of us developing the curriculum. And we open in November. And, you know, it's modernelderacademy.org. It's a social enterprise. So 50% of the people are on scholarship. So you'll have an investment banker

and a social worker walking down the beach together on a break to sort of like basically help teach each other, you know, what's the next era of their life going to be about? So, and people from all ages and from all over the world, our first week open to the public,

we have a 31-year-old junior elder from Kenya coming as part of the cohort. And the cohort's 12 to 18 people, not big. And it's a week long. And it's a pretty transformational experience using the four lessons in my book, Wisdom at Work, to evolve the first lesson, to learn the second lesson, to collaborate the third lesson, and to counsel the fourth lesson. And the real intent of it, and we actually have already a second location we're looking at, which is because we can see the demand is so high, what we really believe is people in midlife need a place where they can connect with each other and talk about what's

next. But there also needs to be a curriculum that helps them understand that, you know, they had adolescence in their, you know, during their teen years, but you can have middle essence, which is a word that's not known outside of academia, but middle essence is what happens typically in our fifties. And it's basically going through a bunch of changes again. For women, it's menopause often. And for men, there's something called andropause, which is the male version of menopause. But it's not just that. It's the variety of other things that are happening both to our bodies and our emotions in ways that we as a society haven't properly acknowledged.

Yeah. in ways that we as a society haven't properly acknowledged. So, yeah. So we talk about the midlife, the U-curve of happiness and the midlife atrium and what it means to be a modern elder. Yeah. And I think it's interesting you use the phrase in ways that we don't acknowledge. And my sense is it's actually much worse than that in ways that we fight like hell. Oh, for sure. Not to acknowledge.

And we want to step away from. And we don't want to say, I'm that person. But I agree with you. I do believe we're in this moment where there's a reclamation or there's an opportunity for a reclamation of wisdom associated with and grace associated with a window of life where normally it's like, well, I don't want to tell you my age. And yeah, I think we're- Could we make aging aspirational again? Right, right. I think we're in an interesting moment around that.

There is a, we've run different retreats and things like that over the years where we brought together different people. And there's, as you were talking about the two folks walking down the beach together, a picture popped into my mind, which is kind of like a commentary on this, and on my own judgment and assumptions. We had a group of people that were spending three or four days together in this giant old log cabin on top of a mountain in Salt Lake City. And one afternoon, I took a look out back on a break during lunch,

and I see one of the people who was a guy in his sort of like mid to late fifties sitting off on a rock. And next to him was the youngest guy in the group who was maybe 20 years old. And they had, they had something open, like a little document or something that they're looking at. And, and I took a picture and because I was like, you know, this is a beautiful shot of these two people sort of like working together. And I, and I showed both of them that picture once I had it developed a month or two later. And I said, this is such a beautiful moment. I want to capture it.

We have, you know, here's the older gentleman sitting next to the young guy, mentoring him and helping him answer questions and like, you know, trend transmitting this wisdom. And the dude in his 50s looks at me, he's like, you got that totally wrong. And I said, what was actually happening? He's like, I was struggling with something with one of my children. And I was asking the 20-year-old for insight,

for wisdom to help me through. I was like, wow. I mean, look at the assumptions that I made right there. Yeah. I was like, wow. I mean, look at the assumptions that I made right there. Yeah. The fact that wisdom can flow in both directions is a fascinating phenomenon. It's not one that we have much history with, frankly, in society. But in a technological era, it's going to become more and more evident.

Yeah. I hear you. So this feels like a good place for us to come full circle. So as we sit here in the name of this Good Life Project, if I offer out that phrase, to live a good life, what comes up for you? I think to live a good life is to live a curious life. It's to live a life that is fascinated by possibility and fascinated by what we haven't learned yet. And so I believe curiosity is the elixir for creativity and innovation as well as for resilience. So I think the ultimate good life is a life full of curiosity. Thank you. Yes.

Thank you so much for listening to this episode. And thanks also to our fantastic sponsors who helped make the show possible. You can check them out in the links that we have included in today's show notes. And while you're at it, be sure to click on the subscribe button in your listening app so you never miss an episode and then share the Good Life Project love with friends. When ideas become conversations that lead to action, that is when real change takes hold. See you next time. The Apple Watch Series 10 is here. It has the biggest display ever.

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iPhone XS or later required, charge time and actual results will vary. Mayday, mayday, we've been compromised. The pilot's a hitman. I knew you were gonna be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're gonna die. Don't shoot him, we need him! Y'all need a pilot? I knew you were gonna be fun. Tell me how to fly this thing.

You know what the difference between me and you is? You're gonna die. Don't shoot him, we need him! Y'all need a pilot?