Chip Conley: How To Become a Modern Elder, Create A Second Wave & Regenerate Your Soul

What if we reimagined aging not as something to fear—but rather as something aspirational? Rich's guest for this exploration is 'Modern Elder" Chip Conley. A hotelier and hospitality maverick, Chip is the founder of America’s second-largest boutique hotel company and former Strategic Advisor and Global Head of Hospitality for Airbnb, where he was instrumental in guiding the founders of this fast-growing start-up into the global hospitality brand it is today. In addition, Chip is a New York Times bestselling author and founder of Modern Elder Academy, the first midlife wisdom school dedicated to transforming aging. Today’s episode is also viewable on YouTube: bit.ly/chipconley681 More about Chip + show notes: https://bit.ly/richroll681 To celebrate the 10th anniversary of 'Finding Ultra', Rich is giving away 50 personally inscribed copies. Enter to win by signing up for his mailing list HERE. Peace + Plants, Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

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• 1:06Chip Conley?

  I knew I was really unhappy, and I had thought about going to the Golden Gate Bridge myself and jumping. I really was at that place of saying, I don't know how to disengage from this identity I've created. I was giving a speech in St. Louis, and after the speech, I was sitting and signing books, and I went unconscious. I guess I was out for like four or five minutes, and they called the paramedics, thankfully, and I was on the ground. And next thing I knew, I was coming to, I had no idea where I was or what had happened. The paramedics put me on the gurney, and that was the first time I went flatlined. They had to bring out the paddles to shock me back to life. And over the next 90 minutes, I flatlined nine times in 90 minutes.

• 1:49Chip Conley?

  And what happened for me was, I had to look at my life and say, is this the life I want? I was having, I guess, a midlife crisis, but it was ultimately the thing that helped me to say, get out of jail free chip, you don't have to die, and I can start rewriting the script of how I want to live my life.

• 2:24Rich Roll?

  The Rich Roll Podcast. Hey, everybody. Welcome to the podcast. On tap today is a fantastic discussion. It's a discussion about how to reimagine aging, to view aging not as something to be feared, but instead as something aspirational, an opportunity to share all that accrued wisdom, to channel it into a second act, and leverage it to deepen and make more meaningful your connection with life, your connection with others, and of course, your connection with self. My guest for this odyssey is my new friend, Chip Conley. A hotelier and hospitality maverick,

• 3:07Rich Roll?

  Chip founded America's second-largest boutique hotel company, and subsequent to selling it, served as strategic advisor and global head of hospitality for Airbnb, where he was instrumental in guiding the founders of this then-small-but-fast-growing startup into the global hospitality behemoth it is today. In addition, Chip is an in-demand public speaker and multiple TED Talker. He's a New York Times bestselling author. He sits on the board of Burning Man, and he's the founder of something called the Modern Elder Academy, which is the first midlife wisdom school dedicated to transforming aging.

• 3:50Rich Roll?

  This one is pure gold, and it's coming right up. But first...

• 4:02Rich Roll?

  Okay, Chip Conley. So this one is obviously oriented towards those who are approaching or find themselves amidst that midlife stage of their professional career and their personal life. But honestly, it's also really for anyone and everyone who's just looking to weave a little bit more meaning and fulfillment into their life, into their professional life in particular. And especially, it's for those who have pursued a certain career track for some time and are now in that place of contemplating new possibilities. We discuss overcoming our fear of aging. We talk about navigating midlife transitions,

• 4:44Rich Roll?

  what it means to be a modern elder, the critical role elder wisdom can and should play in the workplace, and how to think about receive and give mentorship. We also talk about mindset, we talk about identity, getting clear on what is essential to being fulfilled. We discuss the difference between pursuing accumulation versus the pursuit of attunement, and the reimagination of continuing education as well as community living. Final thing before we dig in, if you're inspired by this conversation with Chip, as I suspect you will, he's hosting a few workshops in Baja in June and early

• 5:25Rich Roll?

  July, and he just launched this new eight-week online course entitled Designing Your Purposeful Path to Work, which starts June 4. For links to all of this, check out the show notes on the episode page at richroll.com, or you can just go directly to modernelderacademy.com. Chip is a wonderful man, he's a beautiful spirit. This conversation is going to leave you pondering your life a little bit more deeply, and hopefully put a smile on your face along the way. So, here we go. This is me and Chip Connolly. Well, it's good to see you. It's been a couple of weeks since we met down in Miami. I haven't shaved since. I'm trying to cultivate my modern elder look.

• 6:08Chip Conley?

  Your modern elder look.

• 6:09Rich Roll?

  My modern elder aesthetic.

• 6:10Chip Conley?

  You're looking wise.

• 6:11Rich Roll?

  And I can't wait to dig into all of this with you today. And I was reflecting, as I was driving in, wrapping my head around, you know, how to approach this with you. And top of mind is a conversation that I had just a couple of days ago. We had this guy, Mike Fremont, in here, who's 100 years old. Like, he turned 100 this year.

• 6:31Chip Conley?

  Wow.

• 6:32Rich Roll?

  And he set like the world record for the marathon at age 90. He holds like all kinds of age group running records. And, and he kind of kicked it off by saying, "I'm having the best time of my life. Like, I'm the happiest now that I've ever been." You know, and he's like, he's a little hard of hearing, and you know, he's 100 years old. But like, to hear him say, like, "Oh yeah, like, life is really great right now", is something, you know, counterintuitive, but also like, right in the sweet spot of, you know, your lane and the things that you're passionate about.

• 7:04Chip Conley?

  What's fascinating is there's a societal narrative on aging and then there's a personal narrative. The societal narrative is if you can survive your midlife crisis around 45 or 50, on the other side of that, you have disease and decrepitude and then you die.

• 7:18Rich Roll?

  Right.

• 7:19Chip Conley?

  And the reality is the personal narrative on people's aging is very different than that. And there's something called the U curve of happiness. It's gotten a lot of social science research attention. And the idea of it is, once you hit around 47.2, although your mileage may vary, with each passing decade after that, you get happier and happier. So you're happier in your 50s than your 40s, 60s than 50s, 70s than 60s, and you start to see some leveling out and a decline in happiness around the last two or three years of your life. So if you're living to 100, and maybe, who knows how long he'll live, you know, he's probably still on the stride going up.

• 7:56Rich Roll?

  Yeah.

• 7:57Chip Conley?

  But what's so strange is the gap between the personal narrative, which is actually people do get happier as after age 50, and the societal narrative, which is you're all downhill after about age 40.

• 8:09Rich Roll?

  But I would suspect that that happiness quotient would calibrate to, you know, you still finding purpose and meaning in however you're spending your time, right? Like, the way we think about aging is so unhealthy, it's like this black hole, like, you know, there's, and I know you've talked about this, there's childhood, there's adulthood, and then what? Like, what happens for 40 or 50 years? Like, we don't really talk about it, you've dubbed it, elderhood, but short of housing people in these horrible, you know, sort of assisted living situations, we haven't really created any kind of modern, forward-thinking kind of programming around like how to get

• 8:53Rich Roll?

  the most out of these many decades later in life.

• 8:56Chip Conley?

  You know, if you're gonna live till 90, which is, you know, very likely for a lot of us, my parents are 84, neither one of them has been a huge athlete, and they're on a six-week vacation right now at age 84. So if you live till 90 and you're 54, which is a little bit younger than you, you're halfway through your adult life if you start counting at age 18. And we don't think about life that way. We very much underestimate how much adult life we have ahead of us. We also overestimate how long we're going to be an invalid. And there's something called compressed morbidity in the medical field. And it means that, in essence, the time of your life when you're sort of on the verge

• 9:37Chip Conley?

  of death is a much shorter period, on average, than it used to be. So you've got, you know, what Mary Catherine Bateson would call is, she calls it the midlife atrium. She says that having additional life, having additional years, because longevity in the year 1900 was 47 on average, and by the year 2000 it was 77. She says, all of those additional years are not like having extra bedrooms in the backyard of your house, like you're old longer. No, she says, it's like having a midlife atrium. And the midlife atrium means there's light and air and additional space happening in the middle of your life. So you're in midlife longer.

• 10:17Chip Conley?

  And yet, we have very little, in the way of society, resources, tools, or even thinking around what midlife is supposed to be.

• 10:26Rich Roll?

  Yeah. But historically, we were much better at this. Any kind of indigenous culture has a reverence and a respect for their elders that we somehow forgot as we modernized.

• 10:38Chip Conley?

  Well, we is the Western society. It still exists in indigenous societies. It still exists a little bit in Asia and Latin America. But quite frankly, everywhere in the world, you know, if you had a choice between going to grandpa or Google to go get your information, you go to Google.

• 10:54Rich Roll?

  Right.

• 10:54Chip Conley?

  And I think that that has meant that we have lost that opportunity to tap into the wisdom of the elders. But I don't think we're going to go back to that. I don't think the, I don't think we're in an era where it's going to be all about reverence of the elders again. I think it's about relevance. So how do we help our elders? And elders, if you could be an elder at 40, If you are, I mean Terry Crews, who you had on the show recently, um, you know, he's an elder and he's in his 50s, but he was an elder when he was in his 40s amongst some of the people he was hanging around. And so how do we create a relationship between the young and the old in such a way that they can learn from each other?

• 11:33Rich Roll?

  Yeah. My wife's father, he passed away a couple of years ago at 91, but he was a civil engineer in Alaska in Anchorage and was instrumental in the construction of a lot of the downtown buildings and institutions, including like their fabulous art museum. And he worked with, a lot of the construction entities were run by Native American, you know, people who have that reverence and respect. And even though he was like losing his sight and all of these things, they kept like hiring him for all of these jobs up until like the very end of his life. Like he was gaining, making more money and more

• 12:15Rich Roll?

  kind of like meaningfully employed than he had been throughout his career, which speaks to relevance and him continuing to find meaning in his life. And yes, we're not going back to that, but I think this idea of relevance is so important as exemplified, you know, through your experience with Airbnb. So maybe we can kind of step back a little bit and kind of contextualize this with your, with your story.

• 12:40Chip Conley?

  So my story is, uh, you know, grew up in Southern California, went up to Northern California for college. We both went to Stanford. You swam, I played water polo.

• 12:49Rich Roll?

  You were a water polo player. We were a couple of years separated, but we have some common friends from that era.

• 12:54Chip Conley?

  And we used to swim in the same pool. Um, and I went to business school there and a couple of years out of that business school, started a boutique hotel company.

• 13:03Rich Roll?

  You went straight to Stanford Business School, right? That would rarely happen these days.

• 13:08Chip Conley?

  It really doesn't. I was 23 when I graduated from Stanford Business School, very unusual. Seth Godin and I were the two youngest people in our class.

• 13:14Rich Roll?

  I heard on, when you, when you were on Tim Ferriss's podcast, talking about the kind of mastermind group that you formed with him and you guys would get together and talk about business ideas and you ended up co-writing a book with Seth, right?

• 13:26Chip Conley?

  I did.

• 13:27Rich Roll?

  In business school.

• 13:28Chip Conley?

  I did. And we, and we're, we're deep, close friends because we were both sort of weirdos in, in business school. Um, so a couple of years out of, out of business school, I started a boutique hotel company called Joie de Vivre, um, meaning joy of life. And, uh, Created 52 boutique hotels around California. And then I sold it and we can come back to that possibly. And I sold it partly because my life was falling apart. We'll come back to that. Let's go forward and say, okay, I created some space in my life. And that's when I was called by Brian Chesky, the co-founder and CEO of Airbnb. And I quite frankly, 10 years ago, didn't know what Airbnb was. You know, I was this hotelier who was about to get disrupted by Airbnb.

• 14:12Chip Conley?

  And I didn't really know what this was. And he asked if I could be his in-house mentor and help this little tech startup become a global hospitality brand. And so I joined and quickly became known as the modern elder at Airbnb, which was not exactly what I was, the title I was looking for.

• 14:34Rich Roll?

  Yeah. At age, what, you were like 52?

• 14:37Chip Conley?

  I was 52, Brian was 31, average age in the company was 26. So do the math. And they called me the modern elder partly because they said, Joe Gebbia, one of the other co-founders said, Chip, you're as curious as you are wise. I was like, oh, well, I don't love the title, modern elder. But if a modern elder is someone who's as curious as they are wise, and they know how to have the right alchemy of curiosity and wisdom in their life, that describes me pretty well.

• 15:04Rich Roll?

  Sure.

• 15:04Chip Conley?

  And

• 15:05Rich Roll?

  And I want to, sorry to interrupt, but I do want to put a finer point on how you were able to kind of cultivate that curiosity in the wake of a successful exit from your company. Maybe we can come back to that because I think it is related to one other thing that you want to talk about.

• 15:20Chip Conley?

  Yeah, yeah, I'll come back to that. And I'll just tell a little bit of that Airbnb story now.

• 15:24Rich Roll?

  Sure.

• 15:25Chip Conley?

  It sounds good.

• 15:26Rich Roll?

  Yeah.

• 15:26Chip Conley?

  So yes, I joined this place. I'd never been in a tech company before. I thought they wanted me for my knowledge of the hospitality industry. But frankly, it didn't really matter how many rooms made cleans in an eight-hour shift in the Airbnb host world. So You know, within, actually, it was the third day on the job, I was in a meeting where Brian had said, "Listen, go spend a lot of time with the engineers. You've never been in a tech company before. Start learning the lingo." And so I thought I was supposed to be the mentor, but at the end of an hour meeting with a bunch of engineers, I knew I was the intern. I was like Robert De Niro, you know, in the movie with Anne Hathaway, but he came in as the intern

• 16:10Chip Conley?

  and he became the mentor. I was actually, came in as the mentor and now I'm the intern. And what I realized is that I didn't understand the language, but that didn't mean I couldn't learn it. When I say the language, I meant like, in that meeting, someone turned to me, the guy running the meeting, a 25-year-old guy turns to me and says, "Chip, if you shipped a feature and no one used it, did it really ship?" And I was like, "I have no idea what you're talking about." Shipping a feature? I've never worked in a tech company. Like, so I had to acknowledge that I was not the smartest person in the room. I might have been the most curious person in the room at times and maybe the wisest, but I had to be open to learning. And my father said to me, you know,

• 16:55Chip Conley?

  "Chip, if, how could you turn your fear into curiosity?" And that was a really great reframe for me because I guess, you know, at 52, having run a company for 24 years, taken it from one person to 3,500 people, there was a part of me that in my early to mid-50s, I was thinking, "Oh, what if my last career, you know, step is a big mistake and I'm just a huge failure here?" So I think part of, you know, what really helped was I was willing to be humble and vulnerable about what I didn't know. And often, I was asking questions that helped the company to see their blind spots, or see our blind spots.

• 17:39Chip Conley?

  And I think it was that process that helped me to see that, gosh, you know, more tech companies could use a modern elder. I just watched We Crashed.

• 17:50Rich Roll?

  Right.

• 17:50Chip Conley?

  And, you know, of course, and then there's Super Pumped, and then there's the the Inventor with Elizabeth Holmes. I mean, thank God, there's no Airbnb movie like that, this mini-series, drama mini-series of like, you know, these crash and burn tales. But if you look at it, none of those companies really had a modern elder.

• 18:09Rich Roll?

  Well, it's interesting because you you wrote a blog post about this on your Wisemwell blog. I watched all those founder series, like, I'm fascinated by them, and they vary in in quality. But, you know, the the recurring theme is, you know, ego gets the best of these people when it spirals out of control. But in the example of Super Pumped, which is about Travis Kalanick and Uber, there actually was a modern elder in that context. They had Bill Gurley, who is the benchmark VC, who's sort of the stand-in for the modern elder, but he's butting up against an ego that is not having it. And that, of course, you know, sows the seeds for the downfall of his career.

• 18:48Chip Conley?

  And the big difference for him, and you had Bruce Dunleavy for We Worked, who I went to business school with, same class as me. But investors don't have time to be 24 hours a day in-house at the company. So, you know, Bill or Bruce will come to a meeting and say, okay, what's going on? And but then they go back and they look at the rest of their portfolio. And ultimately, Bill got more involved in the business. But quite frankly, he could see what happens in a meeting. And of course, you'd see some signs of serious hubris. And partly that's because Silicon Valley wants hubris.

• 19:25Rich Roll?

  Right.

• 19:26Chip Conley?

  It's funny, you know, there's an element of like Silicon Valley wants the confident, super pumped CEO, founder, and then they want them to miraculously move from hubris to humility.

• 19:40Rich Roll?

  Right.

• 19:41Chip Conley?

  As a leader.

• 19:41Rich Roll?

  It's the package. Like, if you want the guy who has the massive vision and the audacity to not only dream big, but execute on that, you're going to get the other side of it.

• 19:51Chip Conley?

  You are. And this is why, you know, Brian Chesky, let's talk about him for a moment. When Brian approached me and said, I want you to come in-house and full-time at Airbnb and be my mentor, but also be the head of global hospitality and strategy and a bunch of other things. You know, I had to look at him and say, okay, this guy, I'm 52, he's 31, I'm going to report to him, but I'm going to be his mentor. That's going to be sort of odd. What's it going to be like to report to my mentee? And I had to have a level of confidence that he wanted to learn and that he was, you know, he had the hubris to go out and raise money, but he had the humility to build a culture and a leadership team and, and to maybe even take some direction occasionally from me.

• 20:36Rich Roll?

  Yeah.

• 20:36Chip Conley?

  And so I think that was the key.

• 20:39Rich Roll?

  And that's rare.

• 20:40Chip Conley?

  It is rare.

• 20:40Rich Roll?

  And that's why they're still, they're still the founders and it's functional.

• 20:45Chip Conley?

  It's amazing. I mean, you know, we have three founders at Airbnb. It's over $100 billion company now. It's by far the most valuable hospitality company in the world. And the three founders are still very actively involved. That's never happened before. There's never been a company that has had that. And I'm proud of, I mean, I, I made all kinds of mistakes while I was there and the company would have done well without me. And yet, I am very proud that the three of those founders are still working together as they are because I think the, the glue that needed to happen amongst the three was partly between me and a couple other people who helped them to, to feel that sense of what each of them offered to the company and to each other.

• 21:23Rich Roll?

  What's a, an example of some of the wisdom that you were able to impart and also the receptivity of Chesky and his team to what you had to offer?

• 21:34Chip Conley?

  Sometimes it was as simple as, um, I mean, some of it was just little mechanical things because, you know, one of the things you get better at as you get older is you, you've had the pattern recognition in your life to see what worked and what didn't. And so some of it was simple stuff like Brian, you went into that meeting trying to sell the leadership team on something and you knew there were two people in that meeting on the team who were going to probably be critics of it. What would have been great is if you had spent some one-on-one time with each of, of both of them before the meeting. So they could actually air some of their concerns instead of feeling like they had to actually air it amongst everybody else. Because then you could have adapted the plan a little bit. So that's a simple thing. Or another simple thing would be like

• 22:19Chip Conley?

  at Thanksgiving, we had all been running just crazy, you know, 70, 80, 90 hour weeks, flying everywhere. We're a global company. And the leadership team's families weren't seeing us. And so it was Thanksgiving and I said to Brian, what if you send just a thank you note, maybe a bottle of wine or some flowers to the spouses and family members of all the leadership team and just say, this Thanksgiving, I just want to say thanks to you. Because what's happening behind the scenes, Brian, is, you know, Brian was not in, he wasn't married, he didn't have kids, but he didn't realize that others did. And, you know, behind the scenes, there's this person, the spouse, saying, I don't

• 23:04Chip Conley?

  want you to work this much, you know? And what we needed to really do is respect that. So there's a couple of simple ideas. But we work, you know, I mean, Adam Newman wanted to do a major strategic partnership with Airbnb and Brian, Brian was sort of had some cognitive dissonance on it. He could see some of the value of it at one time. But I said, Brian, you know, this guy is a Messiah, right? You've seen him act that way. How are you going to create a logical business relationship with someone who believes they're the Messiah? So, but it was, I would say that a lot of my wisdom related to emotional intelligence.

• 23:45Chip Conley?

  How do you develop emotional intelligence as a leader when you've had no background in being a leader?

• 23:53Rich Roll?

  Yeah. Why do you think that Brian singled you out for this role? Like, what, I mean, you have this robust history of being a mentor that started, you know, actually quite early in your life and in your career. But why do you think he, you know, A, had the foresight to see the need for a mentor? And what was it about you that he found attractive?

• 24:18Chip Conley?

  So Brian is, got the most voracious appetite for learning that I've ever met in my life. And so he, like when Airbnb in 2011 had this, someone like totally trashed an apartment, he decided to go to the former head of the CIA to learn about safety and security and how he could actually make the Airbnb platform safer. And So he also had been talking to a guy named John Donahoe. So John's a friend of mine. He was, he and I were in YPO together and we were in the same forum. John's the CEO of Nike now. But back then, John was about 10 years ago, the eBay, the eBay CEO.

• 25:01Chip Conley?

  And so Brian, knowing that eBay had some similarities to Airbnb in terms of there was a two-sided marketplace. He was working with John as a mentor, part-time. And so John, I think, said to Brian, you know, you should talk to Chip. And Brian was like, well, tell me more about Chip. And so as Brian learned more, Brian said, oh, man, I want to learn from him. But, but I think what Brian initially was looking for was someone who had the knowledge of the hospitality and travel industry because when I joined the company, no one in the company had that background at all.

• 25:39Rich Roll?

  Right.

• 25:40Chip Conley?

  But I think what he learned over time was he said, I, you know, I hired you for your knowledge, but what I've really gotten was your wisdom. And it's your wisdom of understanding people and leadership and strategy. So, um, so I think, you know, one of the things we get better at as we get older is holistic thinking. Arthur Brooks talks about this in his new book, From Strength to Strength.

• 26:00Rich Roll?

  Yeah, he's coming in soon.

• 26:02Chip Conley?

  Oh, is he?

• 26:02Rich Roll?

  Scheduled, yeah.

• 26:03Chip Conley?

  Oh, man, he's, we're buddies.

• 26:05Rich Roll?

  Yeah, you guys are like, every time in researching like articles and stuff like that, it's like your name and him and his name always kind of are appearing in the.

• 26:13Chip Conley?

  I love, you know, he's so, like, speaking of super pumped, I mean, this is a guy who's adrenalized. And I really enjoy sometimes sparring with him, you know, intellectual jousting. But in his book, From Strength to Strength, he talks about, you know, going from fluid intelligence to crystallized intelligence. Fluid intelligence is very focused, logical, you know, and it's about actually innovating within a certain linear course. But crystallized intelligence is when you are. Looking at things more holistically. Because one of the things that's interesting about our brain is as we age, we actually move from being very focused in the brain to actually having four-wheel drive of the brain.

• 26:56Chip Conley?

  We actually move much more lyrically and logically from one side, the right side to the left side. So, um, which is great because what it means is that we can actually look systemically and holistically at things and connect the dots.

• 27:10Rich Roll?

  It makes sense because you've accumulated so many experiences over the course of your life. You get to a point where you're able to synthesize all of that information. And, and I feel like just, you know, at 55 now, like an ability to kind of see things a little bit more clearly than I could.

• 27:27Chip Conley?

  Yeah.

• 27:27Rich Roll?

  In younger years.

• 27:28Chip Conley?

  I, I think the, whether it's wisdom or intuition, pattern recognition, you get to a place where the, the right answer just sort of pops up. Um, and it's not because you've done some mathematical theory to get there. It's actually coming from your lived experience. I like to think of, um, wisdom as metabolized experience, which leads to distilled compassion. And, and it's, so in both cases, the metabolizing of experience, how am I digesting my experience? Leads to understanding yourself more, the world more, and then being able to have some level of compassion. Because I think wisdom without compassion, um, you know, is, is just, you know, doing something for yourself.

• 28:10Rich Roll?

  Right.

• 28:11Chip Conley?

  Um, one of the things I did, you know, early on, Rich, when I was 28 years old, so I started my boutique hotel company when I was 26. At 28, I realized I was clueless. I knew I was clueless at 26 too, because I never, I like, I bought a motel in San Francisco. In a bad neighborhood. Um, it was, it was a pay-by-the-hour motel, which if you know what that means, it means it was very popular at lunchtime. People would come and have their little affair at lunchtime and then go home, uh, or go back to the office. And so at age 28, two years into it, I realized like, I don't know if this business is going to work. And we had the, the San Francisco Loma Prieta earthquake. And I was like, oh my God, we have no business now. So I started doing something that actually I would recommend everybody do.

• 28:54Chip Conley?

  I mean, it's, it's just simple about metabolizing experience. Every weekend, I would sit down with a diary. Somebody had given it to me as a diary. I didn't use it as a diary. I used it as a place to understand my wisdom. And so I called it my wisdom book. And each weekend, I would create like three, four, maybe eight different bullet points of what I'd learned that week. And often, the learning was painful. It was things like, oh, man. You know, Linda Ronstadt wanted to take over our whole hotel, but I took a day to get back to her travel agent, and they booked something else. So it's like, okay, you know, simple lesson, which was like, okay, if a travel agent is...

• 29:37Rich Roll?

  Move quickly.

• 29:38Chip Conley?

  Yeah, move quickly. I mean, don't, don't, don't waste time. And so, long story short is, every weekend for over 30 years, I sat down and wrote in the, in one of 10 wisdom books, and now Google Docs, with what I'd learned that week. And the value in doing this is it actually allows you to start to metabolize your experience. You could do this for a team. You could say, once a quarter, we as a leadership team are going to do a vulnerable kind of experience, where we said, what was my biggest lesson this quarter? And then let each person speak up about what was the lesson, what did they learn from it, and how they're going to use it moving forward?

• 30:23Chip Conley?

  Because that's a way we start to metabolize experience into wisdom.

• 30:27Rich Roll?

  Yeah, that's amazing. So that's a practice that you still, to this day, do, right?

• 30:31Chip Conley?

  I still do, yeah, yeah.

• 30:31Rich Roll?

  It's sort of a...

• 30:32Chip Conley?

  I don't do it every weekend. So let me be clear, because I want to be fully honest. I do it once a month now. I don't do it every weekend anymore. But I did it every weekend for about 30 years.

• 30:41Rich Roll?

  Wow. It conjures, in my mind, sort of a hybrid between a very directed journaling exercise, where you're going in, you're not just, you know, like doing morning pages where you're vomiting out whatever. You're very intentional about what it is that you're focused on writing about, matched with a practice that, you know, I've been in recovery for a long time. This is sort of like a daily thing, to do an inventory, right? To like, check yourself a little bit. Like, where am I going wrong? How did I contribute to that thing not going well, et cetera? Which leads to, you know, a deeper level of self-awareness.

• 31:15Chip Conley?

  Yeah, it's, I wish someone had told me this. You know, it's such a simple practice, but such a profound one, in the sense of, our life is meant to be examined.

• 31:27Chip Conley?

  But not examined as if we did something wrong. Maybe we made a mistake, but the lesson from that mistake actually makes us smarter for the future or wiser for the future. And so I, you know, I recommend it for, you know, most of the people that I work with or and, you know, I, there's about six CEOs I mentor today, you know, just as friends. I mean, I don't, I don't do it as a, for a living. And I, I tell them, you know, it's really simple, but like so many things that are simple, it's a practice.

• 32:00Rich Roll?

  Yeah.

• 32:00Chip Conley?

  And you have to do it. Otherwise it won't mean anything.

• 32:04Rich Roll?

  We should mention that the pay by hour hotel Fleabag Motel in the, in the Tenderloin District of San Francisco became the Phoenix. I've stayed there many times. It's such an epic hotel and, you know, such a diverse, dynamic neighborhood. I was in San Francisco this past weekend. I did not stay at the Phoenix. I ended up staying at the, the proper hotel, which is on the edge of the Tenderloin. The Tenderloin has really not got, not gotten much better, you know, since I lived in San Francisco.

• 32:33Chip Conley?

  Thirty-five years ago, and it's actually worse than it was thirty-five years ago. It's one of the few neighborhoods in San Francisco that hasn't gentrified. Um, yeah, it's, it's a, it's a seedy neighborhood and it's, uh, but there's a lot, it's, it is seedy and there's a lot of rich history there and a lot of really interesting cultural things. I was on the board of Glide Memorial Church, Cecil Williams Church in the Tenderloin for many years and just beautiful. There's a lot of humanity there. It's sort of like going to India.

• 33:01Rich Roll?

  Yeah, yeah, yeah, yeah. But the, the Phoenix became known as like the rock and roll hotel. Like all the bands stayed there, like just legends of, of music over the years, which is pretty cool. Like, was that an intention going into it or did that grow out of?

• 33:17Chip Conley?

  I was a twenty-six year old. I was a twenty-six year old who said, you know, I want to get into the boutique hotel business because it seems as if it's about to take off. So Ian Schreger and Bill Kimpton were the first two US boutique hoteliers. I was the one right after them. And I was like, they're, they're successful. I want to be successful too. And so I said, each time we would create a hotel, let's imagine a magazine that defines the hotel. And I, and because magazines and boutique hotels have something in common. They're niche oriented and lifestyle oriented. So that first hotel, the Phoenix, was based upon Rolling Stone magazine. And we came up with five adjectives that defined Rolling Stone. Funky, irreverent, adventurous, cool, and young at heart. And everything we did in creating that first hotel had to come back to those five adjectives.

• 34:01Chip Conley?

  And then miraculously, what we found was the people who fell in love with the hotel were people who would use those five adjectives to describe themselves on a good day. So it was like you are where you sleep. So that's what a boutique hotel is. It's sort of like an identity refreshment. It's aspirational. And so every hotel, yeah, so the first hotel was all about rock and roll bands because at 26, like, oh, yeah, I'd love to have, you know, Nirvana and Pearl Jam and Red Hot Chili Peppers staying here all at the same time on their way to becoming famous bands. And that happened a lot. Those three bands actually toured a lot together. So that's how it started. And then all 52 of the boutique hotels were based upon different magazines.

• 34:39Rich Roll?

  Yeah, so each one had its own magazine.

• 34:40Chip Conley?

  It did. Or sometimes a mixture of two. Like, there's a Hotel Vitali in San Francisco. Closed to the pandemic. So that was, that was dwell meets real simple. So modern, urbane, fresh, natural and nurturing. And so was, you know, so in some ways, I was like an armchair psychologist.

• 34:59Rich Roll?

  Right.

• 35:00Chip Conley?

  By saying, okay, what are the, some of the personalities out there who would like to see a hotel? That's their perfect habitat.

• 35:07Rich Roll?

  Yeah, well, creativity is central to this. A knack for marketing, some foresight about where this industry was headed. It's hard to imagine at this point, a world without boutique hotels. Like, no young person is staying at a Hyatt or a Hilton.

• 35:22Chip Conley?

  Well, they're actually staying in Airbnb.

• 35:23Rich Roll?

  Well, yeah, exactly. Like, yeah, right.

• 35:26Chip Conley?

  Actually boutique hotels were sort of a precursor for Airbnb.

• 35:29Rich Roll?

  Yeah, of course, like a bespoke environment, right? And just having stayed at the, at the proper, like that chain and many others owe its legacy to, you know, this kind of legwork that you did many years ago.

• 35:42Chip Conley?

  Yeah, and if you look at, if you go into almost any full-service Hyatt or Hilton today, they are trying to be like a boutique hotel. The bar is sort of central. The music is definitely not the music of 20 years ago. The design is very different than it used to be. So I think, you know, what the chains realized and then ultimately they bought many of the boutique hotels. My company is part of Hyatt. Kimpton is part of Intercontinental.

• 36:08Rich Roll?

  The irony of that.

• 36:08Chip Conley?

  Yeah, Marriott hired Ian Schreger, like, okay, there we go. The bottom line is, you know, the big hotel chains realized that they needed to get hip because the customer wanted more experience. They didn't just want a boring predictable experience.

• 36:30Rich Roll?

  Back to this idea of creativity. It's interesting that, you know, out of business school, your initial kind of career path was commercial real estate, not exactly known for creative inspiration, right? Just buying office space and leasing it, et cetera. So how did you reconcile that creative spark that I'm sure you had some self-awareness around and maybe a latent desire to be an entrepreneur with being in that track? And then ultimately getting to the point where you were capable of manifesting it?

• 37:01Chip Conley?

  So, you know, it's funny, between my first and second year of business school, I worked in New York for Morgan Stanley's real estate division.

• 37:08Rich Roll?

  That's so hard to visualize you doing that.

• 37:11Chip Conley?

  I know, I know. But sort of classic, like you're a business school student. I mean, I was 22 between my first and second year of business school. The fact I was wearing suspenders, smoking cigars and making deals as a Morgan Stanley real estate guy was sort of beyond me. But, and they loved me and gave me some great job offers, you know, after business school. But I just knew, I think the question I had in my mind was, what do I want to be when I grow up and what's going to take me there? Because actually the amount of money they were throwing at me and the amount of prestige they were going to give me, they even knew that I wanted to be, you know, maybe back in the West Coast sometime soon. So they're going to like bring me to New York for a year and then, you know, help run and open the office in LA, the real estate office there.

• 37:56Chip Conley?

  You don't do this for a 22 or 23 year old.

• 38:00Chip Conley?

  But I turned it down. I turned down all the other job offers. I took a job out of business school for $2,000 a month, $24,000 a year, which was crazy. I mean, the average salary out of business school at that point was about $85,000 to $90,000 a year. But I took it because it was working for a creative, what I thought was a creative real estate development company that was basically redeveloping what was called Showplace Square, which was south of Market. And I just thought, you know what, I'm gonna go work there. And the guy who ran the show and founded it said you could become a partner within a year. And so I went to work there. But it wasn't creative enough. I mean, I thought, I chose creativity over

• 38:42Chip Conley?

  money. And even the creative real estate development thing I went to do wasn't creative enough for me. So that's when I, I get to know a guy named Bill Graham, Bill Graham, the concert promoter. So Bill Graham was building Shoreline Amphitheater down in Mountain View and on the peninsula in the Bay Area. And our CEO, founder, wanted me to do a deal with Bill Graham. So we were gonna be his partner on Shoreline Amphitheater. I was like, okay, well, good luck. I mean, Bill's got, Graham's got the money, he knows how to develop. What's our part in this thing? So ultimately, there was no deal to be made. But Bill Graham pulled me aside, said, I like you, Sonny. He says, and at this point, I was 25. I like

• 39:24Chip Conley?

  your chutzpah. I like your, you know, you're a mensch. You know what you really need to do is you really need to create a hotel in San Francisco for the rock and roll bands. Because I have people coming to the Warfield and the Fillmore, and they're coming to Great American Music Hall. And they, there's, the only place they go is an old place called the Miyako, that was in Japan Town, which ultimately became the Hotel Kabuki, which is a Joie de Vivre hotel. And they said, you know, there's no great place for them to stay. And that's when the light bulb

• 39:53Rich Roll?

  Wheels started to turn.

• 39:54Chip Conley?

  You know, over my head and I was like, okay, maybe that's what I should do. So I went to the founder of our firm and I said, I have a really creative idea for you. And I told him what Bill Graham had said to me and it's like, dude, we're not going to get in the hotel business. Like we'll lose our shirts. It's a terrible business.

• 40:11Rich Roll?

  Yeah, that's the thing with hotels, right? Like if you want to lose a ton of money, get into hotels.

• 40:15Chip Conley?

  Yeah, exactly. Same with restaurants, you know, it's a sort of a... But I just said, you know what? I'm gonna go do it. And so I started this company, you know, on my 26th birthday and, and, you know, and bought the motel on a 40-year land lease for $800,000. Can you imagine buying a 44-room property on an acre of land in San Francisco for $800,000? You can't buy a condo for $800,000 in San Francisco.

• 40:39Rich Roll?

  A garage.

• 40:40Chip Conley?

  Yeah, so that's what I bought and here we are 36 years later and I still own the the Phoenix, although we only have about two and a half, three years left on the land lease.

• 40:51Rich Roll?

  So how did you, that story aside, like how did you transcend that? That kind of conventional wisdom around hotels are the way to lose money? I'm thinking about one of those, a scene in one of the Ocean's Eleven movies where Brad Pitt, like he, it appears that he bought the Standard Hotel on Sunset and he's like hemorrhaging all the money that he had stolen in the earlier movie? And everyone's making fun of him.

• 41:13Chip Conley?

  That's so funny. That particular property, um, the, before it was bought by, um, Andre Blanche, uh, and made it into the Standard, I had it in escrow. But it was an old Jewish convalescent home. And I'll never forget, um, so this is, you know, now we're getting in some good stories. I walked through it after we were in escrow and this older Jewish woman came up to me and pulled on my shirt, on my shirt sleeve and she says, "Are you the guy who's going to be actually buying this and throwing us out?"

• 41:42Rich Roll?

  Oh no.

• 41:42Chip Conley?

  And I just had this crisis of conscience and I said, "Not gonna do that."

• 41:49Rich Roll?

  We'll let Brad Pitt do it.

• 41:50Chip Conley?

  We'll let Brad Pitt do it, exactly. So what, so what did, I think what made us different? And the reason we succeeded is we got clear that, you know, the reason a person chooses a boutique hotel is because there's an aspirational lifestyle piece to it. Now Ian Schreger, who was really one of the first, he and Bill Kipton were the two first boutique hoteliers. They had different perspectives. So Schreger's perspective was it's all about being cool, hip, and maybe even narcissistic. And so all of his, you know, all of his hotels were about, you know, getting behind the velvet rope. Sure. And Kipton's was much more sort of homespun, European, more like an inn kind of experience, where you have a good restaurant there and a wine hour.

• 42:35Chip Conley?

  But they, they sort of kept playing the same game over and over again. And my point of view was like, geez, let's, there's so many different kinds of personalities out there. Let's have this very schizophrenic company where we have 52 different hotels with all kinds of different personalities that we're actually serving. And so that, you know, that's how- Right. But that's riskier because some of those aren't going to work. It's very risky. It's riskier and it's, and in some ways it's stupider because we were like, we were like a branding agency. Every single time we were creating a new hotel, it was a new brand, a new market we were going after. But it was very creative. It was so much fun to create a hotel based upon Vanity Fair meets Outside Magazine. Yeah. Which was a place called Costa Noa, a luxury campground. And so it was just, I,

• 43:20Chip Conley?

  I loved it until I hated it. So can we talk about that story now? Yeah, let's talk about that. Oy vey. Oy vey, Rich. I was so, oh man. So first of all, let's go back to, I was 26. So one of the things we haven't talked about yet is, so I played water polo at Stanford. I was in a fraternity at Stanford. My, I was Stephen Townsend Connelly Jr. My dad was, you know, Stephen Senior. My dad was a marine captain in the, in the reserves. I went to the same high school as my dad. My dad was my baseball coach. I was the star pitcher. My dad was the scout master and an Eagle Scout, and I was an Eagle Scout as well. I went to the same high school as my dad, played water polo and swam like my dad.

• 44:03Chip Conley?

  Um, then went to Stanford University like my dad. That's heavy. Got a girlfriend. There's a lot. Got a girlfriend in freshman year of college, just like my dad did. Now you're really betraying your truth. Exactly. So I was like, oh my gosh. So I was on this path. Now I did join a different fraternity than my dad did and I did play water polo. You were a fidel? Yeah, that's where all the water polo players were. All the water polo players were there. But I had a secret and the secret was something that I was way subliminal. But I was gay and I, I, you know, how was I ever going to tell my dad, the marine captain? You know, Steven senior, not Steven junior, chip off the old block that I was gay.

• 44:44Chip Conley?

  And so what happened was in my early twenties, when I went to work for Morgan Stanley in New York, that was the first time I ever walked into a gay bar. And I was like, oh man, I, you know, it was like in Wizard of Oz, when it goes from black and white to technical color, that's sort of what it felt like. And I was like, okay, but it was hard. And my process of coming out as someone who'd been an all American athlete and in a fraternity and the world I lived in, it was back then, I mean, today it's a totally different story. But back then it was pretty hard. So fast forward a couple of years later, I am now the CEO at age 26 of a boutique hotel company. Well, first, let me just, let me just backtrack a little bit. Like, how did it go with Chip Senior? Chip Senior. Chip off the old block.

• 45:29Chip Conley?

  He really, so dad actually initially took it well. And then not so well and wanted me to go to reparative therapy. And so I, I, I mean, can I talk, I can talk about this stuff. Okay. So I ended up going to therapy with a guy named Bernie Zelbergeld, who wrote a book called Male Sexuality. He's no longer living and he set me up with a surrogate. Because Bernie spent a bunch of time with me and said, listen dude, you know, you might be bisexual, but I'm pretty sure you're straight and you just need to, you know, have the right woman with you. And there's this woman, Annie, and Annie is so hot. Annie is so hot and so you're gonna have sex with Annie every two weeks. She's gonna report back to me about what actually happened.

• 46:14Chip Conley?

  And then you're gonna, you're just gonna, I can tell you.

• 46:16Rich Roll?

  Having sex like in a transactional way?

• 46:19Chip Conley?

  Lights fucked out and I'm gonna like, yeah, actual sex. And this is also, this is during AIDS. This is like, this is 1984, 83, 84, 85. So, you know, of course we were safe and I was having sex with her. But I was, I was going back to Bernie and saying, you know, it doesn't feel the same as it did with Victor.

• 46:39Chip Conley?

  And so, um, long story short is, uh, dad finally got used to the idea that, you know, reparative therapy wasn't gonna work. And, um, and the reason this is relevant to my boutique hotel career is because when I started my hotel company, there was an element for me, like, I needed to prove myself. I needed to go say, okay, I am going to be successful. And because I'll be successful, you will admire and like me. And therefore, um, it's my way of making up for the fact that I felt like I had both disappointed my dad, but also that I was not normal or I was not as good as my fraternity brothers because I was gay and they were straight.

• 47:21Rich Roll?

  Right, but you, you could have stayed at Morgan Stanley and checked all of those boxes. So there was something percolating inside of you that you, you needed to find a new and different way that was more in alignment with your blueprint.

• 47:33Chip Conley?

  Isn't that interesting?

• 47:34Rich Roll?

  And be successful in that regard.

• 47:35Chip Conley?

  You know, it's very interesting, Rich, because there's an element for me, like somehow my true north knew. And again, this is stereotyping, but as a gay man, I had a great design eye. Okay, is that inborn? I don't know what that says about gay men, but guess what? Gay men tend to have that. I'm pretty empathetic by nature. I'm pretty good at understanding other people and being open to being in service of them.

• 48:02Chip Conley?

  And so for all those reasons, boutique hotels made a lot of sense. And so I started this company. It grows to be the second largest boutique hotel company in the US. Along the way, my sense of identity, my sense of who I am from age 26 to, let's say, 47 or 48, is dudes, you know, I am this founder and CEO of this company that's grown to 3,500 employees.

• 48:31Chip Conley?

  And then I had, it's like the world changed almost overnight. So it was early 2008 and I could see the great recession coming based upon our numbers. I had written a book, so I've written five books. And my third book I had written a few months earlier called Peak: How Great Companies Get Their Mojo From Maslow. It became a huge hit and I was giving speeches on it and I was loving that. I loved writing. I love speaking. It's like almost sudden, all of a sudden, like the thing that had been my calling, there's a new calling and the new calling is knocking on the door. And I feel like a little bit, you know, unloyal, disloyal, because the new calling was this writing, speaking thing.

• 49:14Chip Conley?

  And then I had, so I had a foster son, African-American foster son, who was having some trouble with the law as an adult. And I had a long-term relationship potentially ending. I was running out of cash because of the Great Recession. And then one of my closest friends, who has the exact same name I have, his name is Chip, not exactly the first name. So Chip takes his own life. He dies by suicide. And so to go to the funeral of a friend of yours who has the exact same name, strange name, and I was sort of in the early stage of A Dark Night of My Own Soul, was really uncanny. And then

• 49:56Chip Conley?

  Soon after that, I, so Gavin Newsom, who's the governor of California, was my first mentee when I was 35 and he was 28, before he was the mayor of San Francisco, before he was the governor of California. So I went to his bachelor party at AT&T ballpark.

• 50:11Rich Roll?

  Yeah.

• 50:12Chip Conley?

  And I hit a triple out to the warning track and I was sliding to third base at age 48, 47, 48, and I was, I broke my ankle. And then I got a back, a septic condition in my leg. And so I was on a strong antibiotic and I was giving a speech in St. Louis. And after the speech, I was sitting and signing books and I went, I went flatline. I didn't go flatline, I went unconscious.

• 50:36Rich Roll?

  Like literally at the signing table?

• 50:38Chip Conley?

  At the signing table, I went unconscious, they put me on the ground. I guess I was out for like four or five minutes. And they called the paramedics thankfully. And I was on the ground and next thing I knew, I was coming to, I had no idea where I was or what had happened. The paramedics put me on the gurney and that was the first time I went flatline. So I flatlined, they had to bring out the paddles to, you know, shock me back to life. And over the next 90 minutes, I flatlined nine, nine times in 90 minutes. And what happened for me, and how this relates to my whole history, was I had this moment of, you know, I can, we can talk about what it's like to go to the other side.

• 51:19Rich Roll?

  Yeah, definitely.

• 51:20Chip Conley?

  It was a true NDE.

• 51:21Rich Roll?

  I definitely want to hear more about that.

• 51:22Chip Conley?

  Um, but what, what it really forced me to look at is how I had the, the, the hotel year's wake up call. I had to look at my life and say, is this the life I want? I was having, I guess, a midlife crisis in, in some way, but I was, more than anything, I was having what Brené Brown, my friend, would, would call a midlife unraveling. Like it was, everything was so tightly wound and it needed to unwind some. And so.

• 51:54Rich Roll?

  Did you have self-awareness of that at the time? Or were you kind of like pushing that down and just in the kind of move forward?

• 52:02Chip Conley?

  I knew I was really unhappy. I knew I was unhappy. I knew that when I was at Chip's funeral or at his, at his memorial service and people were telling their Chip stories and I had thought about going to the Golden Gate Bridge myself and jumping.

• 52:19Chip Conley?

  I really was at that place of saying, I don't know how to, I don't know how to disengage from this identity I've created. The identity that defined me was this successful entrepreneur who's creative, who creates an amazing culture, who happens to write books and give speeches and do TED Talks. And all of this was the, it was like the Wizard of Oz.

• 52:44Rich Roll?

  It was a very aspirational identity that anybody would, would want to have and obviously was the, the manifestation of what you had dreamed about.

• 52:53Chip Conley?

  And?

• 52:54Rich Roll?

  So how could you be unhappy in that condition?

• 52:56Chip Conley?

  I was unhappy because I, first of all, I didn't, I, it wasn't creative enough. Let's go back to that. I had created a company that was a creativity company, but by the time we had 3,500 employees, and now we're in the Great Recession and we've grown, opened 15 hotels in the last 21 months, like in the worst of times. Like, I, I was just trying to keep the-

• 53:22Rich Roll?

  The lights on.

• 53:23Chip Conley?

  The lights on.

• 53:24Rich Roll?

  Yeah. It's about spreadsheets and managing people.

• 53:26Chip Conley?

  And I loved writing. And then I was also had all this other stuff happening in my personal life, you know, my son and foster son and my relationship ending. And, and so what happened was I, you know, I had this flatline experience. I had Man's Search for Meaning, Viktor Frankl's book, in my backpack. Um, I, because, you know, that's my way, my way of knowing how dark I was at that time, was I was carrying around Viktor Frankl's book as the reminder that I was not in a concentration camp. The concentration camp was in my own mind.

• 54:00Rich Roll?

  In your mind, yeah.

• 54:01Chip Conley?

  So, I, while I was in the hospital for a couple of days while they're doing all these tests, and ultimately they sort of said, I think, we think you're allergic to Augment and the antibiotic you're on. So, I was reading Viktor Frankl's book about being in a concentration camp, and I came up with an equation, despair equals suffering minus meaning.

• 54:20Chip Conley?

  Despair equals suffering minus meaning. So if suffering is ever-present, and if you're a Buddhist, that's the first noble truth of Buddhism is, you know, suffering is ever-present. Then despair and meaning are inversely proportional. So when you're going through a really crappy time, the key is to ask yourself, what's the meaning? And it really did take me 20 years back to when I said, okay, my wisdom book, you know, what did I learn this week? So I really, I got very fixated on, what am I learning? What am I learning? And what's the meaning in this? And ultimately, within two years, less than two years, I'd sold the company at the bottom of the Great Recession. I had ended the romantic relationship I'd been in for a long time that wasn't working.

• 55:05Chip Conley?

  I'd gotten my foster son out of prison, out of San Quentin, because a federal judge let him out and said, he's innocent, he's not guilty, his constitutional rights were abridged.

• 55:19Chip Conley?

  And I was on a path to saying, I'm ready for the magic. I mean, I'm ready to actually create space in my life and see what emerges, because I've spent the last two dozen years building this identity. And I don't, and I haven't, it's not a facade. I mean, I was, the whole time, I was living my truth, but I was also getting to a place where my, I was so fixated with the identity, that I wasn't actually giving space for the new creativity to come in. And so, yeah, and that was not long after that, that Airbnb came calling.

• 55:52Rich Roll?

  So in the midst of experiencing that level of despair and the self-awareness that you had to find or attach some meaning to it, walk me through the process of how you identified that. Because I think, you know, there's probably a lot of people who are experiencing some level of despair. It's been a really hard couple of years. Is the idea that there is universal meaning in all suffering? Or is it that you have to find a personal connection, like your own definition of how it could be meaningful for you?

• 56:23Chip Conley?

  Well, let's use Frankl for a minute. So if Victor Frankl and, you know, folks were in the concentration camp. What he says in his book is that when he saw people having hope and had a sense of the other side of this, not false hope, the people who actually died quickly were the ones who said, by this date, we are going to be out of here. And that was a false hope because they had no control over them being released by that date. But there was more of a focus on hope for what the future will be and how this experience will actually create maybe a better life for them.

• 57:06Chip Conley?

  And so that's not a bad way to look at it because what we do know is that when we're going through difficult times, it is exceptionally character building. It can be, not for everybody. Sometimes people give up. Sometimes people do whatever they do and where they drink, they use distractions, they use alcohol, they use drugs, they use porn, they use whatever it is to distract themselves from the learning. It's work sometimes as well. So I think the key for me was to ask myself, how is my character? This may not be a resume builder, surviving a downturn.

• 57:49Chip Conley?

  So how do we, to use some David Brooks thinking, how do we move from the resume values to the eulogy values? And the eulogy values are the values that people will say about you at your funeral. And they're the character qualities. And I think it was around that age, in my late 40s, that I realized I'd spent my life building a resume. And I'd built some character qualities along the way, but I was never really focused on how am I developing those character qualities? And if you want a time to develop your character qualities, use the dark time to do that. Because it's an exceptional time and it's a time where you actually often have to break habits.

• 58:30Rich Roll?

  Yeah. I have my own experience with that.

• 58:33Chip Conley?

  Yeah.

• 58:34Rich Roll?

  Yeah.

• 58:34Chip Conley?

  Tell us.

• 58:35Rich Roll?

  It's painful. Well, I mean, I'm not going to bore everyone who's listening to this.

• 58:38Chip Conley?

  They're listening. They're on this show because they were like, "You."

• 58:41Rich Roll?

  But I mean, you know, my, my, I had a version of that reckoning at, at 40 and it was sort of a collision of a health scare with an existential crisis about how I was living my life. I was a corporate lawyer at the time and very unhappy, but also very much in the checking the boxes and, and, you know, trying to make sure that I was the dutiful son to parents with high expectations, et cetera, you know, something that you know quite well, and had to, you know, really deconstruct all of that and figure out who I wanted to be. And then spent a decade trying to figure that out. I'm still trying to figure it out. And I found, you know, a modality that I leveraged was endurance sports and all of the kind of quiet time that comes with that, that allowed me to,

• 59:23Rich Roll?

  you know, develop a level of, of self-connection that I was lacking at the time and ultimately leading me, you know, kind of into a more intuition-based, heart-centered place to be open to what was next. And, you know, Airbnb didn't call, but, you know, slowly other opportunities came and that's kind of why I'm sitting here today.

• 59:44Chip Conley?

  And that evolution and having it be on display for others has been incredibly cathartic to people to see your, your process, especially, you know, you're from 40 to 55. You know, that is, I would say, you know, U-curve of happiness shows that 47.2 is the low point. You know, again, your mileage may vary, but from 40 to 55, a lot's going on. I use another emotional equation. Disappointment equals expectations minus reality.

• 1:00:17Rich Roll?

  Right.

• 1:00:18Chip Conley?

  So disappointment equals, so it's around 40 to 50, 55, that you start to come face to face with the expectations that you have for yourself. The perfect spouse, that you're supposed to be President of the United States, how much wealth you're supposed to have, the second home you're supposed to have, the kids who are perfect. And, you know, in your 40s, you come face to face with the fact that none of that's actually happening. And you also may come face to face with the fact that this success script that you were handed by your parents.

• 1:00:51Chip Conley?

  Is not the script that you want to write for yourself.

• 1:00:54Rich Roll?

  And is not leading to the fulfillment that was implicitly promised.

• 1:00:58Chip Conley?

  That's right. And so, you know, lucky for me, at 2022, I came out of the closet because it forced me to actually come face to face with my success script from my parents and my lovely parents. I love my parents and, you know, they've been, after a rough initial time, they've been incredibly supportive and loving and, you know, love the fact that they're on a six week vacation right now at age 84. But what I can say is that, you know, being able to deconstruct the success script in such a way that you recognize that you're the screenwriter of your own life and you need sometimes some guidance for how to write that screenplay,

• 1:01:42Chip Conley?

  partly because you may have constructed your life in a certain way and it's not just like, oh, okay, now I'm going to go do this other thing. No, you actually have three kids and you get a spouse and you've got a mortgage and you're actually helping your ailing parents. At the same time, you're helping your teenagers. So you've got the sandwich generation going on. And so the process of doing that, I witnessed my father, my father, who dutifully became a banker, like his father, around his early 40s, said, you know, fuck this. I don't want to do this. And he created a business when he had me at Stanford, my sister about to

• 1:02:24Chip Conley?

  go to Stanford, and then another sister going to go to UC Berkeley a few years later. And he started a company at a time where it was really not opportune. So my father's been a role model for me in many ways.

• 1:02:36Rich Roll?

  Interesting.

• 1:02:37Chip Conley?

  And I, you know, it is around our 40s and 50s. And some people's reaction to all that is go get the, you know, the red Ferrari or have the affair. And You know, I mean, often, that's just another form of a distraction.

• 1:02:54Rich Roll?

  Yeah.

• 1:02:56Rich Roll?

  I want to get into the mentorship piece, but before that, I'm not letting you off the hook on that near-death experience.

• 1:03:02Chip Conley?

  Yeah.

• 1:03:03Rich Roll?

  I want to hear what that was like specifically.

• 1:03:06Chip Conley?

  Well, since it happened nine times in 90 minutes, and I had one particular nurse there by my side four of those nine times, and each time I would come out of my NDE, I would say to her, here's what I saw, and she would say to me, that's what you said last time, and the last time was only about six minutes ago.

• 1:03:25Chip Conley?

  So here's what I saw, and, you know, I've hung out with a lot of NDE folks. There's even a, I'm fascinated by festivals because I'm a founding board member of the Burning Man nonprofit, and there's a festival in northwestern Spain called the Pilgrimage of the Near Death Experience. And everybody who has had a near-death experience is put in a coffin that's open, and you have a parade of coffins going down the street, and you're waving at everybody, and everybody's drinking, and it's, it sounds sort of weird and macabre, but, um, so my experience was this. The first thing I noticed was that I was in a mountain chalet, so like, maybe, you

• 1:04:10Chip Conley?

  know, let's say eight or 10,000 feet in some mountain range. It was like, maybe a summer day, so I didn't notice any snow, but there was this huge skylight in the living room, the upstairs living room, and the skylight was open, and there was light coming in, and there was a kaleidoscope of colors that was actually being projected onto the wall. I was about maybe eight or 10 feet in the air, just sort of floating. I didn't see myself, I didn't observe myself, I just knew I was not on the ground, I was sort of observing from that place.

• 1:04:47Chip Conley?

  There were birds chirping, it was gorgeous, and it was sort of quite beautiful. And then the thing that was most noticeable was on the ground, it was this beautiful wood floor, and on the ground, there was this frangia pani scented, so like a tropically scented oil, it was very thick, like a viscous oil, that was actually, made it, created a sheen on the floor, and the oil was going toward the staircase going downstairs.

• 1:05:15Chip Conley?

  But it's sort of like that Heinz 57 commercial anticipation. You know, it's like the oil was dripping down the stairs exceptionally slowly.

• 1:05:27Chip Conley?

  So what I noticed more than anything around this, there was no other people, there was no there was no white light other than this light coming from the skylight, which was like a white light that led to the kaleidoscope of colors on the wall. What I noticed is how sensual it all was, the listening to the birds, the smelling of the frangipani, the beauty of it all. At some point, I actually touched, you know, my arm projected longer so I could touch the ground and touch the oil. And I think more than anything, what I felt was this sense of spaciousness and slowness. Now, I had, in 2005, we opened the Hotel Vitali.

• 1:06:10Chip Conley?

  And the Hotel Vitali had slippers in the room, and one slipper said slow and the other slipper said down. So if you had your slippers on, it said, slow down. And that was one of my ideas for this hotel that was supposed to be like, almost like a spa hotel in the financial district. Slow down. So I was in my own NDE that was just telling me to slow down. That is the experience I had. That's what I take from it. The other thing I take, so because, because again, the dripping of the oil was so slow. So, you know, I might be out for two minutes or three minutes when I had my NDE and I'd come back and I felt like I'd been out for hours or days.

• 1:06:50Chip Conley?

  But more than anything, what I got from it was just this deep sense of just slowing down. And when I slowed down, I realized that I'd spent my life running away from my emotions.

• 1:07:04Chip Conley?

  And what I, what I recognized was that I, because the, you know, the recession had come on and I was trying to figure out how to keep my company afloat, I was just a manic, crazy person.

• 1:07:20Chip Conley?

  And I didn't want to be that one anymore. And I'd spent my life, I'd spent since age 21 meditating, but I'd stopped meditating at that point. I was no longer meditating. And so my exercise, I started practicing, you know, my meditation every morning and late in the day, and I just slowed my life down. And as I slowed my life down, I realized that I thought I loved what I was doing. And I did, in some ways. My ego did. But one of the things that Carl Jung and Christian mystic Richard Rohr have talked about is the fact that the, and Richard Rohr has come to our Modern Elder Academy- Oh, wow. As a student, as a student, at 79 years old. Really? Yes. We'll talk about this, we'll talk about this when we talk about M E A.

• 1:08:03Chip Conley?

  But, um, so what I noticed was that when I slowed down, my ego started to melt. And Richard Rohr and Carl Jung have both said that your primary operating system for the first half of your life is your ego. And for the second half of your adult life, it's your soul. And yet, none of us are issued operating instructions of how to move from driving automatic to driving stick shift. And it's almost like, you know, you're on a San Francisco, you know, hilly road during a rainstorm, and you're on Hyde Street trying to drive up with the cable car, you know,

• 1:08:46Chip Conley?

  the metal from the cable car tracks, meaning you're spinning your wheels. Because the process of moving from ego to soul, or from automatic to stick shift, is a, there's a, there's a complexity to it. And I had to have an N D E to recognize it and to slow down to see that I needed an operating system shift. And that's what happened. And I, it's a deeper, longer story than that. And I wrote a book called Emotional Equations about it. But it was ultimately the thing that helped me to say, get out of jail free, Chip. You don't have to die. You don't have to be like your friend Chip, who had took his own life.

• 1:09:30Chip Conley?

  And I can, I can start rewriting the script of how I want to live my life. And, and ultimately, my experience going to Airbnb-

• 1:09:42Chip Conley?

  Was a perfect segue for me because instead of being the sage on the stage, the hero, heroic CEO, I was the guide on the side.

• 1:09:53Rich Roll?

  Right, worker among workers.

• 1:09:54Chip Conley?

  I was the worker amongst workers and I was the guy helping these three founders, along with some other people. I mean, it was not just me. But I was really tightly wound with them to help them be successful. It's sort of like what a parent does with a child. Your ego doesn't have a space in that relationship.

• 1:10:13Rich Roll?

  Yeah, what a beautiful insight and experience to have to take this thing and attach meaning to it. It's such a specific experience, right? And in the many kind of flat lines that you had, that same vision recurred to you?

• 1:10:30Chip Conley?

  Oh, yeah. The nurse kept saying, "You're so funny. You keep telling me the same thing."

• 1:10:34Rich Roll?

  Right. And so, what do you make of that? I mean, you could say, "Well, this is your unconscious mind, your subconscious, trying to get your attention." Or you can go down a more metaphysical rabbit hole with the whole thing. You being on the board of Burning Man and all of that, I'm going to predict that you're seeing this as more of a metaphysical experience.

• 1:10:58Chip Conley?

  Yeah, I mean, I saw it as this opportunity. I mean, I saw it as an opportunity for me to have the courage to change everything. And the metaphysical side of it was very much, you know, this divine intervention and this sense like, "Okay, you get another chance, Chip."

• 1:11:22Rich Roll?

  Right. You're not ready to go, but you're ready to be reborn in a different way.

• 1:11:27Chip Conley?

  Yeah, for sure. Interestingly, my first hotel was called The Phoenix, the mythological bird that rises from its own ashes. So I was ready to be regenerated, which we'll talk about in a few minutes. I was ready for regeneration. But... I didn't know how to do that. And that's actually, I think, a lot of people. There's a lot of people who are sort of in that place of realizing, this isn't working anymore. I don't need to have an NDE to learn that. But how do I re-script my life? How do I sculpt it in a different way? How do I break through the blocks? And, you know, the habits that are in my way?

• 1:12:08Rich Roll?

  Yeah, and I think tragically, all too many may have some version of that epiphany, but are feeling trapped in the circumstances of their life due to the things that you mentioned. The mortgage, the responsibilities, et cetera. And so then they live out their remaining days in tension between those two things and unable to kind of figure out a path forward that would kind of resolve that internal conflict.

• 1:12:41Rich Roll?

  Let's talk about mentorship. Because when I think of you and I look at you and in the limited amount of time that we spent together, to me, like, you're this wise teacher. Like, you have the teacher gene. I think you thrive in circumstances where, you know, whether it's onstage or one-on-one in the modern Elder Academy, where you're imparting, you know, some experience-based wisdom that you've accumulated. I know you studied philosophy in college, et cetera. So this feels like very... My sense is that it feels very natural to you, not that it isn't like, you know, sort of trained over the years. But the mentorship thing, to me, feels like your real self eking out, you know, earlier in life before the NDEs and all of that.

• 1:13:26Rich Roll?

  I mean, the fact that at 35, you're mentoring Gavin Newsom. Like, when did the mentorship thing start? And how has that become a thing? Like, kind of what role does that play? In terms of you being a mentor and the importance of mentorship in general.

• 1:13:41Chip Conley?

  So quite specifically with Gavin, he was a hospitality entrepreneur. He had a company called Plumpjack.

• 1:13:49Rich Roll?

  I remember that, living in San Francisco.

• 1:13:51Chip Conley?

  Exactly.

• 1:13:53Chip Conley?

  There was a wine, there was a wine store, and there was a restaurant, and then there was a hotel.

• 1:13:57Rich Roll?

  Right on Fillmore, like a Union Street area.

• 1:13:59Chip Conley?

  Yeah, exactly, Cow Hollow. Long story short is, his sister came to me, Hillary, and she said, "You know, my brother could learn a few things from you." And I'd met her a few times, and I'd met him, but I didn't know him as well as I knew her. "Would you be open to mentoring him?" And of course, she hadn't asked him about this. And I said, "Sure." And partly, she had read, at that point, I think I'd written, I had written, maybe, no, she hadn't written a book yet. But I'd written some columns, some business columns, and she just sort of knew who I was. So, long story short, is every Friday, Gavin would come down to my office in Union Square, from his offices in Cow Hollow in San Francisco,

• 1:14:44Chip Conley?

  and we'd sit down and talk. And then ultimately, he had brought me into his Plumpjack organization to help mentor some of the other leaders there, and lead some offsite retreats for them. And then he ran for the Board of Supervisors in San Francisco, so he became on the Board of Supervisors, which is like the city council. And then he became mayor. And when he became mayor, that's where it amped up, because now here's this guy who's, I don't know, at that point, he was in his 30s, I think.

• 1:15:11Rich Roll?

  Pretty young, yeah.

• 1:15:12Chip Conley?

  Yeah, he was in his late 30s when he became mayor, if I'm not mistaken, or early 40s. But he was a very young mayor, and San Francisco was going through a really difficult time. And so now, I showed up at his office every Friday. He was showing up at my office in the early days. Now I'm showing up at City Hall, room 200, and... Being his consigliere, I mean, I was sort of like the person he sought counsel from. And then he did the same thing. So with his like the chief of police and the fire chief and, you know, the head of human services and we would actually do offsite retreats and I would help mentor some of them. And so that was a fascinating experience and then he ultimately became governor and we still stay in touch pretty closely.

• 1:15:57Rich Roll?

  It's a trip, though. Like you're like, what am I doing?

• 1:16:01Chip Conley?

  I mean.

• 1:16:02Rich Roll?

  Mentoring the mayor of San Francisco.

• 1:16:03Chip Conley?

  Well, it's weird. And, you know, and it was like Chip, everybody in the office knew Chip brings, you know, Gavin's lunch and Chip's lunch in these sacks. And there's actually San Francisco Magazine once did a story about it, like this picture of me coming to Gavin's office with a sack lunch. And so, you know, and I've been lucky enough to be the CEO for the Burning Man, the mentor for the Burning Man CEO Marion Goodell, Liz Lambert, one of the best-known boutique hoteliers in the US, and of course Brian Chesky and others. And I, you know, the, what I love about mentorship is in a great mentorship

• 1:16:45Chip Conley?

  relationship, you as the mentor may learn as much as they will. And when I was at Airbnb, I had over 100 mentees and over the course of seven and a half years, which is a lot. And I learned as much from them as they did from me. And Brian once said this to me, Brian Chesky once said this to me, he said, Chip, you know, you teach me EQ and I teach you DQ. EQ being emotional intelligence, DQ being digital intelligence. And I think if we could look at mentorship, we have five generations in the workplace for the very first time. And if we could realize, and, you know, here's a couple of other stats, over 40% of Americans now have a boss that's younger than them. So my relationship with

• 1:17:26Chip Conley?

  Brian was not as unusual as it might have been 25 years ago. So we have something to learn from each other. And being able to create mutual mentorship relationships where one person knows one thing that the other person wants to learn and vice versa, you know, it wouldn't take a lot of matchmaking technology in a large company to match employees as mentors. Because quite frankly, the beautiful thing about a mentorship relationship is it's, it's.

• 1:17:58Chip Conley?

  It's free form, it's affordable, you know, it doesn't cost anything. And you know, bottom line is, you know, Deloitte has shown in their studies that when people have a mentor in an organization, they are substantially more likely to stay in the organization. And in an era like we're in right now with the Great Resignation, where companies are saying, you know, we're losing people left and right. You know, one of the best things you could do, not just for, you know, wisdom and knowledge transfer, but also for retention, is create mentorship programs within an organization, right?

• 1:18:33Rich Roll?

  There's great kinship between the idea of mentorship and the modern elder idea, right? Before we move off of this, though, I think, I'd like to hear a few thoughts on going about finding a mentor, or soliciting your services as a mentor. I think there's a lot of people who think mentorship means, I'm going to email Seth Godin every single day for two years until he finally relents and becomes my mentor. We think of these fancy names, people that we would like to have on call, but that's not really the heart of what it is. Like, I'm always talking about the fact that there are mentors all around you. Like, find the people in your environment and figure out how you can contribute to their lives if you're going to solicit their input into yours.

• 1:19:18Chip Conley?

  Yeah, and be careful of, like, leading with the M-word, you know?

• 1:19:23Rich Roll?

  It's like, whoa.

• 1:19:24Chip Conley?

  The M-word, you know, if you pop the marriage question on the second date, it's a little too much.

• 1:19:30Rich Roll?

  Like, I don't even know you.

• 1:19:31Chip Conley?

  Yeah, exactly. So, the way I would go about it, on either side, mentor or mentee, but maybe let's start with the mentee side, is, let's say there's somebody you want to learn from. Just say, hey, hey, could I take you out for a coffee? Or could we go have tea? Or could I, like, can we just have a meal together? And if they're in your same organization, the likelihood is they're going to say yes. You know, if it's the CEO and you're, you've been in the company a month as an intern, they may not say yes if it's a huge company. But one of the ways to pose it is to say, hey, let's just have a little meal. And I just would love to tap into your wisdom. I mean, don't, don't be shy about saying something like that.

• 1:20:14Chip Conley?

  Or even more specific, you say, I've noticed that you're really good at fill in the blank. I would like to learn from you. Can we just get together once and have a conversation? And then don't expect a bigger commitment than that. But then have the one time conversation. And if it goes really well, and you can see that they're enjoying it as the, as the mentor. Say, you know, in a month from now, could I, could we maybe get together again? And they're likely to say, yes. Do it again. And at that point, if that second one is great, then say, you know, are you open to us maybe creating like a, a short term mentor relationship? Maybe we get together once a month or every two weeks for an hour.

• 1:20:58Chip Conley?

  And I ask questions and you give me some homework assignments, et cetera. But get at the point where you're ready to ask that, get specific about what you're looking for. And, and be clear that you're committed to it. I mean, the worst experience for a mentor is when a mentee goes through that whole process and then doesn't take it seriously. Doesn't show up for the meeting or, you know, says, okay, well, you know, I don't have time right now or et cetera. Make the time. If you're not willing to make the time, then don't actually make the ask. But also give it a finite period. Because that's, that way the other person doesn't feel like, oh no. This is a lifelong commitment.

• 1:21:39Rich Roll?

  Yeah.

• 1:21:40Chip Conley?

  The other thing I would just say is there's two kinds of mentorship. There's mentorship that's performance, what I would call performance based and then, and then development based. Performance based is like finite. It's more of a mentorship relationship where you have information I want to learn. I need to ask you questions and you'll be my mentor. But it'll be a finite relationship because I want to learn more about how to run a great meeting. How to understand the travel industry. How to.

• 1:22:15Chip Conley?

  I don't know, code, do simple coding. So that's a finite relationship. It's performance driven in the sense that over the course of a short period of time, you can determine if you've gotten better at that.

• 1:22:27Rich Roll?

  Mm hmm.

• 1:22:28Chip Conley?

  So you can have a lot of mentees. If they're sort of that like that, they're like, okay, yeah, you can ask me questions every once in a while, and I understand you want to learn about this thing. The other kind of relationship is a developmental relationship, and it's a lot more comprehensive, and it's more personal, professional, emotional, EQ. And that's when somebody really just wants a guide, you know? What one of my mentees called me, her confidant. And I said, wow, okay, give me some juicy gossip. And she said, well, no, no. And she's French. She said, when I say confidant, and I mean it in sort of the French way, you're the one who gives me confidence.

• 1:23:07Rich Roll?

  Hmm.

• 1:23:08Chip Conley?

  So it wasn't a knowledge transfer. It wasn't a knowledge transfer, which the first kind of relationship is, like, I'm transferring knowledge. The second kind of relationship is one that's more personal. And actually, the person who's asking the questions is not the mentee. The person who's asking the questions is the mentor. And I'm asking questions about you to help you unlock who you are and help you, guide you, be your permissionary, to help give you the permission to do the things I think that you have the capability of doing. A lot of people think that that's what a mentorship relationship is, and it is. But this first kind is the more finite kind, and allows you to have many relationships,

• 1:23:50Chip Conley?

  because they're, you know, it's specific to a knowledge transfer. So being able to understand what kind of relationship a person wants when it comes to mentorship is pretty important.

• 1:24:01Rich Roll?

  Not to push back, but how many emails a day do you get from people asking to take you out for a cup of coffee?

• 1:24:09Chip Conley?

  Yeah.

• 1:24:09Rich Roll?

  You see, that's the thing.

• 1:24:10Chip Conley?

  It's nice to live in Baja most of the time, because I'm not.

• 1:24:13Rich Roll?

  I get a lot of those emails, and it's like, I don't, you know, I can't do that. Like, I'm not in a position to do that. So I think it is really about who are the people in your environment.

• 1:24:23Chip Conley?

  Yeah, I mean, when it's, listen, if someone has come from out of the blue and I don't know them at all, I mean, I do get a lot of emails from people, and they, you know, they sweeten me up with all the things that they know I probably want to hear. And in those kinds of cases, I'm not going to get on a Zoom call with them, but I will answer two or three questions by in an email. I'll do that. And so for those of you who are listening to this now and you want to send me an email with a couple of questions, feel free to do that because I had people who helped me early on. There are times when I may say, oh, man, I am barraged right now. So I'm going to have my assistant actually tell you to write me back in a month or six months. And then maybe I can answer some questions.

• 1:25:05Chip Conley?

  But most of the time I do answer questions by email pretty quickly, assuming they're really simple and simple answers. But in terms of like someone saying, hey, can I get, you know, to do a quick Zoom call with you? It's like, I think one of the lessons we've learned in the last two years is doing a simple Zoom call will wear you out if you do, you know, 12 of those in a row. And so for me, I also like to test somebody. You know, if I say, if someone comes to me and says, you know, they want some of my time and I'm really, really barraged with stuff right now and I can't give any time, like come back to me in three months or six months. If they come back to me in three or six months and I can see that they've got something, I'll be, I'll take it a little more seriously.

• 1:25:49Chip Conley?

  Not because I didn't take them seriously the first time, but because they've shown me they have some reliability and some desire. And therefore I'm going to try to reciprocate if I can.

• 1:26:06Rich Roll?

  I want to talk about what it means to be a modern elder, defining what a modern elder is. But to kind of contextualize it, when I think of your tenure at Airbnb, coming in as a mentor, kind of emerging from that as this modern elder and, and the success that that relationship engendered in terms of the company's prosperity. It seems to me that that should be like a Harvard Business School case study. Maybe it is, I don't know. But because it was so fruitful and productive, why doesn't every company institute some version of that because, you know, it was so valuable?

• 1:26:46Chip Conley?

  Well, it's, the good news is the venture capital community and private equity community took notice and it led to a lot of those companies sort of saying, how are we going to? You know, the way venture capital and private equity works is often the person who's put in charge of the young CEO is a young. Partner or young associate at the venture capital and private equity firm. So they're not necessarily the person who has

• 1:27:12Rich Roll?

  It's not Bill Gurley.

• 1:27:13Chip Conley?

  It's not Bill Gurley and it's not somebody who's really going to have the wisdom, or maybe the cojones, so to speak, to say to the person who's out of control, you're out of control. So what I think we're starting to see is a recognition that for their most high-profile, successful companies, they better have a gray hair, you know, you know, in the midst and not just showing up once a month at a meeting, but actually having, creating a mentorship relationship. They're also, you're also seeing a lot more coaches being almost assigned to young CEOs, such that the coach has that role. Now, you know, that's not a bad thing as well.

• 1:27:57Chip Conley?

  Coaches can be spectacular. But, but often if the coach doesn't have the operating experience, you know, they may not be able to keep up with the young CEO when they're talking about what's going on.

• 1:28:08Rich Roll?

  Right, and this is, this is pretty specific to kind of, you know, youth culture-driven business, startup culture.

• 1:28:15Chip Conley?

  Yep.

• 1:28:15Rich Roll?

  But in truth, like the Fortune 500, the Coca Colas, like these huge companies are, are the opposite. It's full of gray hairs, the whole C-suite is ancient. It's almost like they need a young mentor who will be taken seriously to say, here's why you're going to be completely out of business in five years unless you listen to kind of what my generation is looking for.

• 1:28:38Chip Conley?

  Yeah, you know, you're exactly right. Ageism works in both directions. A lot of times when we hear the word ageism, at least in my world, I think of like older people who are being discriminated against. It's the opposite as well. Young people being discriminated against or not being given the opportunity to have a voice in organizations that could use some shaking up. So yeah, it goes, it definitely goes both ways. So, I mean, I think I would just, I would say that we were living in an era where this idea of an intergenerational potluck, where we all bring to the table that which we do or know best, makes a lot of sense.

• 1:29:21Rich Roll?

  Yeah.

• 1:29:21Chip Conley?

  And there's a lot of, there's a huge amount of research on this. So diversity often in companies doesn't think about age diversity. We talk about, you know, race, gender, ethnicity, sexual orientation, but like, okay, age diversity is important as well. And there's a bunch of studies that have come out recently that have shown that when you create age diverse teams, you get the best of both worlds. You get that brilliance, that focus, that quick thinking, young, young spirit, along with the ability to metabolize or think holistically, and think beyond their own ego, and, and actually create that psychological safety. Fascinating study, you know, Google did, that showed that psychological safety was

• 1:30:06Chip Conley?

  the number one ingredient of effective teams, and psychological safety is helped by having age diversity on a team. So I think there's, I think we're in the early stages of realizing that age is an important diversity metric, just like the other ones.

• 1:30:22Rich Roll?

  Sure. For that to work and, and be productive, for that dynamic to be functional between older and younger, it does require a level of like, respect and humility.

• 1:30:34Chip Conley?

  Yeah.

• 1:30:34Rich Roll?

  And the capacity to listen and take seriously what the other person is saying, because I think both, both camps sort of look at each other as dumb dums, you know, like, oh, these old people, they're checked out, they don't know what they're doing. This young, these young people, like, you know, they're, they, their brains aren't even fully formed yet, why should I listen to these people?

• 1:30:52Chip Conley?

  Yeah, I'm, this is part of the reasons, you know, there's, I'm looking forward to doing something later this year. I mean, I'll mention it now, but, you know, we're, we don't even have a website up for it yet, but there's a guy, Michael Hebb, who started Death Over Dinner. So it's a movement globally, over a million people have done this, where they have this Jeffersonian dinners, topics, conversations about the subject of death, and there's, you could have one of three or four or five different topics that you and a few friends can actually talk about over dinner. Well, I think generations over dinner. Generations over dinner is an idea whose time has come.

• 1:31:26Rich Roll?

  I like that.

• 1:31:27Chip Conley?

  Which means you bring a bunch of generations, like three generations, five generations, maybe even seven generations. We have seven generations living still. Bring them to a table and have a topic about, you know, how do you solve climate change? How do you address intergenerational collaboration in the workplace? You know, what happens in the various life stages? And the wisdom would go in both directions. And you could sort of say, oh, we just had a six generation dinner. Or we had a four generation dinner. And so it's something we're going to be launching later this summer. We have a nonprofit called AGE, the Association for Growth and Education, that focuses on intergenerational collaboration. And so keep an eye out for that.

• 1:32:09Rich Roll?

  That's cool.

• 1:32:10Chip Conley?

  At generations over dinner.

• 1:32:11Rich Roll?

  Yeah, I really like that idea. All right, let's talk about the Modern Elder Academy. So walk me through this epiphany and how you've created this amazing thing out of that idea.

• 1:32:21Chip Conley?

  Yeah, you know, so I went down to Baja, so Southern Baja, near Cabo San Lucas, about an hour north, a place called Toda Santos Pescadero area, on the beach. I had a home there. And I was going to start writing my fifth book called Wisdom at Work: The Making of a Modern Elder. So as I'm writing that book, I'm going for runs on the beach. And one day I went for a run on the beach and I had a Baja Aha. I had an epiphany.

• 1:32:47Rich Roll?

  As one is want to do.

• 1:32:48Chip Conley?

  Yes, exactly. We are like, this is an area where there's a midwife for epiphanies. It's like something strange about this particular area that I live in. And the epiphany I had was this, is that, you know, the word adolescence didn't exist in 1903. In 1904, it came into being because a psychologist named Stanley Hall created it and said, hey, there's a life stage that happens between puberty and 18. And it's you're still a child, but you're on the threshold of adulthood. And you're going through emotional and and physical and identity transitions. Okay. And then after the after 1904, now we had public junior high schools and high schools in, you know, more prevalent.

• 1:33:33Chip Conley?

  You had child labor laws. You had people not getting married at age 14 and having babies when they're 15. So long story short is adolescence became a thing. Well, about 20 years ago, a new term got coined called adolescence. Middle adolescence is the adult corollary to adolescence. And it's when you're going through physical and hormonal and identity transitions, often between around age 40 and 60. So the core of core of midlife. So I had this run and I came back. It's like, why do we not have any middle essence school? We have adolescence. We give all this guidance and schools and tools and rites of passage and rituals for people in adolescence, but we have nothing for middle lessons.

• 1:34:17Chip Conley?

  And what if we were to create the world's first midlife wisdom school? A place where people come to cultivate and harvest their wisdom and reimagine and repurpose it. And so this was about four and a half years ago. I had the idea we opened January 2018. And we've had now 2,200 people from 33 countries come to our programs. Usually a week long program in Baja, but we also have programs online as well. And the whole intent is to help people to so reframe their relationship with aging. And interestingly enough, the average age is 54, but 15% 14% of the people who come are millennials. So this is not just people.

• 1:35:01Rich Roll?

  That's super interesting.

• 1:35:02Chip Conley?

  Isn't interesting that people in their 30s.

• 1:35:06Rich Roll?

  And the motivation is I just want to be in a growth mindset and be thinking about this before it becomes, you know.

• 1:35:12Chip Conley?

  And I want to start to mine my wisdom. And I also want to be around people 20 years older than me to learn from their wisdom. So, yeah, and we have a great faculty. We have everybody from Paul Hawken, who's been on your show to Michael Franti, the musician, Matthew Ricard, the famous Buddhist monk. Sherry Lansing has done shows for us. John Donahoe, CEO of Nike, is on our upcoming Purpose online course. So lots of really interesting people who.

• 1:35:44Chip Conley?

  Are helping people, helping all of us to reframe that relationship with aging and look at how we might regenerate ourselves. Because the narrative we have about aging is you age, you work, then you retire. You have three stages in life. You learn till you're 20 or 25. You earn till you're 60 or 65. And then you retire till you die. And if you look at a millennial today, they're like, what the hell is that tyranny of the three-stage life? You know, I want to actually work. I'm going to learn till I'm 20 or 25. And then I'm going to work for 10 years and then I'm going to take a year off. I'm going to do a gap year. And then I'm going to go get a master's. I'm going to learn again. And then I'm going to go retire. I'm going to work for 10 years and start a company and then retire.

• 1:36:27Chip Conley?

  And then go back and get a PhD. And, you know, it's more episodic. It's not like you have these three stages of life that are age-defined. And so that, you know, that led us, you know, the MEA becoming very popular and led us to creating regenerative communities. And this idea of, let's get rid of the idea of retirement communities.

• 1:36:50Rich Roll?

  Yeah, this is the real exciting part.

• 1:36:51Chip Conley?

  Rich, are you going to live in a retirement community someday?

• 1:36:53Rich Roll?

  It's the, it's the most depressing, horrific, you know, aspect of our culture to just warehouse old people and hide them.

• 1:37:01Chip Conley?

  It's a form of age apartheid. Let's like, take those people and put them in a place where we can't see them so they're with each other. And, and let's also recognize that frankly, earlier generations sort of saw it. And, you know, our parents may have enjoyed it. But there's also this weird sense that, you know, back in the old days, if you were working on the factory floor or you were, you know, you were a schoolteacher, you know, your whole life, you got to 60 and you said, thank God, I'm retiring. Because I can't do the factory floor work anymore. Or I'm just so tired of this. Work or, you know, being a house cleaner or whatever it was. And, you know, we have a lot more knowledge workers today.

• 1:37:46Chip Conley?

  And, and I think we have a lot more wisdom workers. That's a phrase that I think is going to come into being. But the knowledge workers can, they can work till their seventies or their eighties or whenever. It's not physical labor that actually defines how they get paid. And so more and more of them are of the mindset like, I'm, I don't want to retire. And, or I can't afford to retire. If I'm going to live till 90 or 95, I can't retire at 62.

• 1:38:10Rich Roll?

  And also that generation is, is far more inclined to be pursuing work that has personal meaning to them than, you know, we're, we're, our legacy is that, that three chapter kind of approach to life. That's what our parents did and we kind of were reared with that sensibility. And now we're in our 50s and 60s. And a lot of us are having those kind of crisis moments. But over the course of those many decades leading up to it, there is a calcification around mindset. This is who I am. This is what I do. Here's what I can expect for my life. Here's how I see the world. This is the people that I vote for. And this is, you know, these are the things that I talk about.

• 1:38:50Rich Roll?

  So one of the critical kind of tools that you leverage at the Modern Elder Academy that I want to hear a little bit more about is just getting really clear on what your mindset is so that you can begin the process of deconstructing it and perhaps, you know, telling yourself a new story.

• 1:39:06Chip Conley?

  Yeah, well, so there's four key colors of our curriculum. The first one's reframing aging, helping people to see that maybe their best life, their best years are ahead of them.

• 1:39:15Rich Roll?

  Right, can this be aspirational?

• 1:39:17Chip Conley?

  It can be, and you know, some things get better with age. I love that your, your listeners and your community is very much about keeping the body alive, but, but you don't, you're, certain things get actually better with age. You know, your emotion, your emotional intelligence grows with age. Your spiritual awareness grows with age. So there's a lot of things that actually get better with age. And, and yes, if you work on your body and your health and your nutrition, it might get better with age as well. You're a great example of that. So there's that reframing aging. Then there's mindset. So there's growth and fixed mindset. We're big fans of Carol Dweck's work at Stanford. And so a fixed mindset is when you tend to think of life as I'm here to prove myself

• 1:40:02Chip Conley?

  and I define success as winning. The problem if you have that point of view as you get older is you stop playing the games you can't win. And that means your sandbox gets smaller and smaller. And as it gets smaller, you actually get more bored because you're not trying new things. So moving from a fixed to a growth mindset means moving from proving yourself to improving yourself. And instead of focusing on winning, you focus on learning. And so you move into this way of thinking and way of being of, okay, I am just a learning machine. I'm not a machine, I'm a learning human. One of the questions we ask at M E A is, what is it that you know now, or have you

• 1:40:46Chip Conley?

  done now, that you wish you had known or done 10 years ago? Think about that for a moment. And then ask yourself 10 years from now, what will you regret if you don't learn it or do it now? And this is how I started to learn how to surf at age 57. Because I live on a beach near a surf break, somewhat famous one. And I was like, ain't gonna be any easier at 67 than 57, Chip. So I gotta start learning that. I also, you know, started learning Spanish. Again, the mantra in my head, the mindset was, I'm too old for this, too old to learn the language, but harder to learn it at 67 than 57. And I knew that I was gonna be living in Mexico, so why not learn it?

• 1:41:30Chip Conley?

  So the first is reframing aging, the second is shifting your mindset. The third is learning about transitions. None of us were taught, you know, and got a master's in T Q, Transitional Intelligence. But midlife is full of transitions. Life is full of transitions. Life is liminal. You're usually in between two things. And yet, we've never really been taught, you know, what's the anatomy of a transition? And how do I architect moving through a transition, whether it's getting divorced, or, you know, changing where I live, or changing my career, or retiring, or seeing my parents to passing away, or becoming an empty nester, or going through menopause, or men go through andropause?

• 1:42:14Chip Conley?

  There's a lot of transitions in midlife. And learning how to understand the three stages of a transition is a big part of our program. And then the final piece of the curriculum is regeneration in all its forms. We have regenerative cell therapy, I mean, stem cell work. Regeneration through understanding a regenerative purpose. But also, and this is where Paul Hawken comes in, regenerative agriculture.

• 1:42:35Rich Roll?

  Right.

• 1:42:36Chip Conley?

  And farming, and that's what leads us to our regenerative communities, our first one being in Baja with 26 homes around a regenerative farm. So instead of living on a fairway, wouldn't you like to live on a farm? And go out into the farm and go harvest with your neighbors and do a potluck once a week? And so now we're taking this to Santa Fe, and we have three different properties in Santa Fe, two of which will be academies, one of which will be a regenerative residential community. And I do believe that we are creating something that is meant to disrupt senior living.

• 1:43:11Rich Roll?

  Right. It's, it's, it disrupts higher education, some form of education, and then this whole kind of area that's so ripe for disruption, senior living. But it's leveraging all this experience that you had as a hotelier. Like, it's not that dissimilar, like, oh, I'm going to disrupt the hotel industry.

• 1:43:34Chip Conley?

  Yeah.

• 1:43:35Rich Roll?

  I, I understand that skill set. Now I'm going to apply it to this other area that is, that desperately we need something better and healthier.

• 1:43:43Chip Conley?

  I've been lucky.

• 1:43:44Rich Roll?

  I think that's really exciting.

• 1:43:45Chip Conley?

  Lucky to be a disruptor twice in the hospitality industry, first as a boutique hotelier, and then at Airbnb. But I, I, you know, you don't start something to disrupt it. I mean, that's, that's not the intent. You start something because you have an idea.

• 1:43:55Rich Roll?

  It's a natural outgrowth of everything.

• 1:43:57Chip Conley?

  That's right. You have an idea, and then the idea sort of takes off. And then we hear from people saying, Chip, you know, long life learning, that's what you're doing. You're not doing lifelong learning, you're doing long life learning. And more and more colleges and universities who are in the process of being disrupted in all kinds of ways right now, Clay Christensen, the guy who created the term disruptive innovation before he passed away five years ago, said, you know, 10, 50% of the colleges and universities in the United States will be out of business in 10 to 15 years. So colleges and universities need to start thinking about midlife wisdom schools or these places.

• 1:44:34Rich Roll?

  And to be fair, a lot of colleges have programs, but they're, it's sort of traditional curriculum oriented.

• 1:44:39Chip Conley?

  It's accumulating knowledge. It's more like I'm going, I mean-

• 1:44:42Rich Roll?

  It's not experiential.

• 1:44:43Chip Conley?

  It's, I'm a 50-year-old sitting in a classroom of 20-year-olds and I'm learning biology or I'm learning, you know, philosophy. But it actually isn't, you know, I wrote, I wrote a white paper called "The Emergence of Long-Life Learning" to study with a PhD who wrote it with me, how do people learn differently at 55? What's important to them? How do they learn differently? And that actually had a huge impact on how we have created our curriculum. Because we actually, at, at MIA, we don't, wisdom is not taught, it's shared. So how do you create the crucible for a collection of 20 people over the course of a week to learn a bunch of things, but then actually share experience and in small dyad partners

• 1:45:27Chip Conley?

  one-on-one with each other, have these conversations of how it's applicable to them. And that, how it's gonna be applicable to you at 55 or at 45 is different than it is at 25. So yes, lifelong learning is a thing. But long-life learning is a subset of it, focused on how to live a life that's as deep and meaningful as it is long. Because we have gotten the quantity right, longevity has grown a lot. The quality is the thing that I think people need to focus more on.

• 1:45:57Rich Roll?

  Hmm. A big piece in trying to engender your life with that level of quality is this transition that you speak about from accumulation to attunement. So speak about that a little bit.

• 1:46:13Chip Conley?

  Yeah, the first half of our life is about accumulating, accumulating knowledge and friends and obligations and, you know, romantic partners and then marriage possibly and children. You get to age 45 or so and you say, "Oh my God, I've got this burden. I've got, like, I've got a lot of baggage." And the second half of your life is now about editing that baggage. So you move from accumulating to editing and you move from the attainment part of your life. And it doesn't mean you don't have attainment throughout your life, you do. But I gotta tell you, and as someone who's like a first-class attainer, you, your attainment at some point, as your ego starts to shift, that operating system of the ego shifts to the soul, you move from attaining to attuning. What's the difference?

• 1:46:57Chip Conley?

  Attaining, when you're in the attainment mode, you will atone later because you may have sharp elbows. You're sort of like, when you're actually attaining, Attaining, atoning. You're very selfishly focused and you might be a gracious person, but you're deeply focused on the finish, the finish line. And it's, you know, that's the hedonic treadmill. It's when we sort of realized, man, I'm, I keep putting finish lines there. And I feel a sense of accomplishment, but I don't necessarily feel the sense of happiness.

• 1:47:30Chip Conley?

  And so, moving from attainment to attunement moves from atoning afterwards to feeling at one. So when you're in the attune phase, you're sort of like harmonizing. So surfing is an attunement sport. You know, you better attune with the wave.

• 1:47:45Chip Conley?

  So many things, as we get older, become attunement, opportunities for attunement. And as we learn how to attune, we actually are, know how to create sort of that psychological safety in a, in a team. We know how to actually create what's called environmental mastery. This is something we get better at as we get older. It's not about the ecosystem or, you know, the dirt on the ground. Environmental mastery means you actually know how to repot yourself in the right habitats and flourish. It's a psychological quality. It's a social science research that shows that as we get older, we understand where we will flourish. And you, you are better and more adept at being able to discern where that will be.

• 1:48:30Chip Conley?

  And so that becomes a part of it as well. And that's attuning with the right environment. It's part of the reason why frankly, at age 50, we sort of get to a place where like, I have no more fucks to give. And I'm not talking about someone's romantic life. I'm actually talking about, I don't want to be in an environment that it feels toxic to me. You might handle it in your twenties or your thirties, maybe even your forties. But in your fifties, your level of patience for it. Isn't, isn't the same. And, you know, one person's toxicity may be another person's beautiful environment. So I'm not saying all environment.

• 1:49:07Rich Roll?

  Right, but there's a freedom and like kind of a liberation and a strength in that.

• 1:49:11Chip Conley?

  Yeah.

• 1:49:11Rich Roll?

  If you're looking at it correctly.

• 1:49:13Chip Conley?

  Yeah, I think it's, you know, this, the self-awareness that comes to like, I know where I flourish. I know what I like. And that's the editing function.

• 1:49:24Rich Roll?

  But also, also, sorry to interrupt, but making sure that that is coming from a higher consciousness state rather than an outgrowth of your fixed mindset at that time about your capabilities.

• 1:49:40Chip Conley?

  Yeah, it's, it's having that openness, again, to the intuition, to the wisdom, to something that actually may emerge that is not scripted for you. And, and that's actually frankly, why in the Great Resignation, in the pandemic, we've seen an enormous explosion in people 45 and older going out and starting their own business.

• 1:50:02Rich Roll?

  Yeah.

• 1:50:02Chip Conley?

  It's huge.

• 1:50:03Rich Roll?

  And a lot of young people not going back to the job.

• 1:50:05Chip Conley?

  And a lot of young people not going back to the job.

• 1:50:07Rich Roll?

  And confusion, like what? Like, people are confused that that's.

• 1:50:10Chip Conley?

  That's right. But what I find interesting on the 45-year-olds and up is we tend to think of it like all the entrepreneurs, like the hot entrepreneurs or under 30. But the fastest growing set of entrepreneurs in the country today are 45 and older.

• 1:50:22Rich Roll?

  Is that right?

• 1:50:23Chip Conley?

  Yeah, yeah, exactly. And so, over 50% of the businesses, you know, the new businesses start in the US are people 50 and older, so.

• 1:50:31Rich Roll?

  Yeah, I love that idea of attunement. Like, in retrospect, reflecting back on my life, like, so much of everything that I'm so blessed to be able to do now has been a process of trying to focus on attunement, having that kind of crisis with what I was doing, you know, relatively early. Like, everybody thinks of 40 as like this pivotal kind of life crisis. And now it just feels cute. Like, I'm 55, like, 40, you were so young.

• 1:51:00Rich Roll?

  And to kind of inelegantly, but eventually fall into this vocation that I feel like meets my skill sets, allows me to continue to develop this growth mindset, and is successful only to the extent to which I can be attuned with you. Like, I can't achieve this conversation for it to be valuable or successful for the person who's listening to it. That is truly a function of the extent to which I can be prepared, but yet completely present and in the allowing.

• 1:51:34Chip Conley?

  So, the opposite of presence is absence. And we live in an absent culture partly because we all have an iPhone in our hand. And when you meet someone who has presence, whether it's a mentor, whether it's a teacher, whether it's a friend, whether it's a romantic partner, when they are present in the moment, you notice it. And this is a quality we get better at as we age. And actually, we're very present when we're young. So, we're very present. You know, you see a child, you know, a two-year-old or a one-year-old, sort of just looking at things, and there's a presence there. And then we accumulate knowledge as we get older, and, you know, in our childhood, and we have scripts that

• 1:52:16Chip Conley?

  we're living, and we're less present. And there's a point at which we become present again. I happen to think it's around when the operating system of the soul kicks in. And when we start to become present again, things come through us. So, I was, most of my life, a can-do-it person. Can-do-it. We had 3,500 employees at Joie de Vivre, and I handed out 3,500 copies of the book, The Little Engine That Could. The Little Engine That Could. Do you remember that childhood story?

• 1:52:46Rich Roll?

  Of course, yes.

• 1:52:47Chip Conley?

  So, the childhood story of this little, tiny little, not a caboose, but the train at the start of the, what would you call the first train? I don't know.

• 1:52:58Rich Roll?

  The engine?

• 1:52:59Chip Conley?

  The engine. Thank you. Yeah, The Little Engine That Could. Thank you, Rich.

• 1:53:03Rich Roll?

  I know this story, it's so imprinted into my childhood.

• 1:53:06Chip Conley?

  So, The Little Engine That Could was the, was sort of brought into duty to do something that was beyond what it thought it could do, and bring all those animals, the circus or zoo animals, up a mountain. So, the can-do-it attitude was very much in my brain, and it was like something I wanted all of my employees to have, and we saw that the, in terms of guest loyalty, a guest who felt that the employees had a can-do-it attitude, that was the number-one correlation with whether the guest would be loyal.

• 1:53:39Chip Conley?

  Can-do-it, can-do-it, can-do-it. I have moved from can-do-it to conduit. So, can-do-it is attainment. Can-do-it is, "I can do it." Can-do-it is rugged individualism. It is the ego-run riot, and it has wonderful qualities about it. But there's a point at which can-do-it, when it can shift to conduit, what happens is you're now the channel. You're the present one who's channeling something through you. And whether this, if Julie was here right now, she'd probably be, we'd get into a very deep spiritual conversation about this, but it is your ability to be the channel, the

• 1:54:24Chip Conley?

  conduit of things through you. And when you get to that state, there's a power that you, that you're conducting that is so much greater than anything you can do in the can-do-it stage.

• 1:54:39Chip Conley?

  And all of this sounds very ethereal, but you know it when you see it and you feel it, sort of like pornography. Definition of pornography from the Supreme Court was, you know, you know it when you see it. Presence and someone's power as a conduit, you know it when you see it.

• 1:54:58Chip Conley?

  I guess I would just say that it's that level of energy. Someone said to me, you know, you've written a book, Chip, about wisdom at work. And all these older people are going to come to you and say, how could I get a job in my 50s or my 40s or my 60s? And this executive recruiter said something that was so beautiful and it relates to this. She said, you know, if you show up with curiosity and passionate engagement in your interview, whether it's in Zoom or in person, what people will notice is not your wrinkles, but they'll notice your energy. And when they notice your energy, they lose track of your age. And that is so true. I mean, I'm feeling it right now. As I'm speaking to you, you're feeling it from me, probably.

• 1:55:37Rich Roll?

  Yeah, it's really powerful.

• 1:55:38Chip Conley?

  It's, there's an energy. And when someone is, and energy is something that's coming through you. It's not just how much weight you're lifting. But it could be. I mean, the conduit can come through you in all kinds of ways. But for me, it comes through me in this role as a teacher now, but also a learner. And, you know, I, I love being in an environment where I can look back and say, I lost five friends to suicide between 2008 and 2010. I wish there had been a great, a midlife wisdom school and a place where they could have done a great midlife edit, such that they could still be on the planet.

• 1:56:23Chip Conley?

  And that's what's coming through me.

• 1:56:26Rich Roll?

  Hmm. Yeah, the conduit. There's something really beautiful about that, that also, you know, I've just noticed when I can inhabit that space, to the extent that I'm capable, that, that is so much more fulfilling than the, you know, striving and the accumulating.

• 1:56:45Chip Conley?

  Yeah.

• 1:56:45Rich Roll?

  To be this, you know, channel for somebody else's success, or to be the connective tissue between two things that then become greater than the sum of their parts.

• 1:56:56Chip Conley?

  Yeah, it's, um, there's a guy named Eric Erickson, developmental psychologist. And he said five words that just to me define this era of life. He said, I am what survives me. And that really means a lot because it's not, it suggests that we've moved to an era of your life where generativity is the key. And he also said, you know, in our midlife and later years, the challenge is between generativity and stagnation. But generativity is different than attain, attainment. Generativity means you're creatively generating things,

• 1:57:41Chip Conley?

  but it's for other people. Often, he meant it in the term of generations, for other generations. So how do we co-generate? How do we create things that are going to survive us, that are going to support other people and help them be a better version of themselves and maybe a better version of me, I mean, through them? So, yeah, I mean, you know, again, this is very much the mentorship language. But I think, you know, one of the things that people need to think about as they get older is their legacy. And not the legacy, the ego legacy. It's not so much, how am I going to be remembered? That's important, but that has a certain ego attached.

• 1:58:26Chip Conley?

  It's more, you know, how will I have served? And when the shift can go to, how have I served? There's something in it that speaks to, what am I doing that's going to live beyond me? That is going to have an influence way beyond me sitting here.

• 1:58:48Rich Roll?

  Yeah. Well, I think that's a good place to kind of lead into the last thing that I want to talk to you about, which is for that person who is contemplating all of this right now, perhaps they're in their 40s or their 50s and they're thinking about what's next or if there is even going to be anything next. And Maybe doesn't have that level of self-understanding or self-integration to really have the intuition to follow wherever they're being led by their curiosity. And perhaps they don't have the budget to go down to Baja and participate in your academy. What are some things that they could be thinking about? Perhaps books they could be reading or ways of approaching that level of self-inquiry

• 1:59:33Rich Roll?

  that could help unlock some of those answers?

• 1:59:35Chip Conley?

  Lots of great books out there.

• 1:59:38Rich Roll?

  Wisdom at Work.

• 1:59:39Chip Conley?

  Wisdom at Work being one of them. But The Hundred Year Life is a really interesting book written by two UK academics talking about the medical world, says that children being born today, there's a 50% chance they're going to live to 100. So how would you curate your life differently if you knew you were going to live to 100? So it's a great book. There's, gosh, what other books do I love?

• 2:00:07Rich Roll?

  Let me just, when you mention that, something comes to mind, which is another tension. The tension between, yes, let's contemplate our lives at 100 and how we can plan for that. But how do you reconcile that with another powerful idea, which is what if you don't have, what if you only have three months or six months or a year to live? How would that change how you're approaching the way that you spend your time?

• 2:00:33Chip Conley?

  Well, that's a very different question. So Laura Carstensen, I'm on her advisory board at the Stanford Center on Longevity, and she's done very conclusive research on this to show that the shorter period of time you have in your life, the more you take seriously each moment. And makes sense. And she looked at it with older people, but also people who had AIDS, people who had a cancer diagnosis that was incurable. And what they found was that when you have less time, you are more mindful in the moment. And that makes sense. You're less focused on the past, you're less focused on the future, you're more focused on the moment.

• 2:01:17Chip Conley?

  And what comes from that is a certain level of life satisfaction and contentment. And so that is, I would just say for anybody who's looking at their life right now and saying, I don't feel very content, my response then would be, how much are you spending time in the moment? How can you do that? Yes, you can meditate. Yes, you can do yoga. Go for a walk with your dog in nature. So during the pandemic, when I was living in Baja and we had no guests because we had to shut down, I would do, I put on my calendar, three hours a day, three days a week. And I called it spying on the divine. And I would go get divinely intoxicated in nature, and I don't mean I brought alcohol or psychedelics.

• 2:02:00Chip Conley?

  No, I was going for a walk with my dog for three hours in different natural, beautiful places around Baja, and just noticing what nature could teach me. The resilience of nature, the interdependence of nature. I was being in the moment. And our friend Dacher Keltner, who started the Greater Good Science Center at UC Berkeley, and is on our faculty, and has a book coming out on awe next year, talks about the various forms of how you can find awe in your life. And for so many people, it's found in nature. So I'd say that is something you can do. You've got a park near you. You don't have to spend any money on that. You don't have to buy a book for that.

• 2:02:43Chip Conley?

  But there's lots of other good books. There's From Strength to Strength that just came out with Arthur Brooks. There's Becca Levy's book, Breaking the Age Code. Becca Levy is the one who actually, in many ways, our program is built on her work from Yale. She was able to show that when you shift a person from a negative to a positive mindset on aging, you give them 7.5 additional years of life. What? It's actually more life than if someone stopped smoking at age 50, or if they started exercising at age 50. So the public health benefit of shifting a mindset around aging has a greater benefit to society, and people are happier.

• 2:03:25Chip Conley?

  And yet, we have PSAs left and right about how we should stop smoking and how we should start exercising. We have no PSAs around how to reframe aging. So, there's, her book, Breaking the Age Code, which just came out in the last month, is a great book. You can do MAA online. I mean, it's, our Purpose Course starts in June, and that is not very expensive, and it's an eight-week course. But, there's lots of ways that, for people to, to actually ask themselves. My blog, my daily blog, it's free, WisdomWell. It's really sort of the best of MAA curriculum. Get a microdose of wisdom every morning.

• 2:04:05Rich Roll?

  Yeah. And maybe adopt that, that inventory, that weekly inventory journaling practice.

• 2:04:11Chip Conley?

  Oh, yes. My wisdom book. Exactly.

• 2:04:13Rich Roll?

  Yeah. Beautiful, man.

• 2:04:15Chip Conley?

  Thank you.

• 2:04:16Rich Roll?

  Really inspiring to talk to you.

• 2:04:18Chip Conley?

  Yeah.

• 2:04:19Rich Roll?

  I want to come down and visit you in Baja.

• 2:04:21Chip Conley?

  Yeah. Maybe we could co-lead a week.

• 2:04:22Rich Roll?

  That would be great. I would, I would love that. I would love that. I need, I need more Chip Conley in my life. If I get anything out of this, like, yes.

• 2:04:30Chip Conley?

  Well, you're, you're helpful for me because, you know, I, it's funny, last quick thought. I'm not vegan, but I started a vegan restaurant.

• 2:04:36Rich Roll?

  That's right. We didn't even talk about that. Like, I had no idea that you were co-owner of Millennium. Like, that's the legendary, I thought, I thought Robin Williams owned it at some point.

• 2:04:46Chip Conley?

  No, no, no, no. Robin Williams went to a lot.

• 2:04:47Rich Roll?

  He used to go there a lot.

• 2:04:48Chip Conley?

  Went to a lot. Woody Harrelson went to a lot. A lot of people went there. By the way, have you seen the movie, the show Bad Vegan?

• 2:04:53Rich Roll?

  Yes. That's a whole other podcast.

• 2:04:55Chip Conley?

  Oh, my God. Oh, my God. I used to go to that, you know, Pure Food, all the time.

• 2:05:00Rich Roll?

  I did, too.

• 2:05:01Chip Conley?

  So, long story short is, you are a reminder for me, because of your show and, and your presence, about me taking care of my body. Because I have, I had prostate cancer, and, you know, and I am

• 2:05:14Rich Roll?

  That's right.

• 2:05:15Chip Conley?

  And back in

• 2:05:16Rich Roll?

  How are you doing?

• 2:05:17Chip Conley?

  And I've, I had a surgery that I only have half a prostate now, but I'm, you know, my PSA is below one, and it was 10.8. So, life is, life is a lot better. And you're that reminder of, you know, take care of myself.

• 2:05:29Rich Roll?

  All right. Well, if I could be so audacious, I will consider this, the first installment in, in ongoing conversations.

• 2:05:37Chip Conley?

  Beautiful.

• 2:05:38Rich Roll?

  I'd love to have you back. So, thank you, Chip.

• 2:05:39Chip Conley?

  Thanks, Rich.

• 2:05:40Rich Roll?

  Appreciate you. Peace.

• 2:05:41Chip Conley?

  We did it.

• 2:05:46Rich Roll?

  That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guests, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, as well as podcast merch, my books, Finding Ultra, Voicing Change, and The Plant Power Way, as well as the Plant Power Meal Planner at meals.richroll.com. If you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts, on Spotify, and on YouTube, and leave a review

• 2:06:29Rich Roll?

  and/or comment. Supporting the sponsors who support the show is also important and appreciated, and sharing the show or your favorite episode with friends or on social media is, of course, awesome and very helpful. And finally, for podcast updates, special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo, with additional audio engineering by Cale Curtis. The video edition of the podcast was created by Blake Curtis, with assistance by our creative director, Dan Drake. Portraits by Davy Greenberg and Grayson Wilder.

• 2:07:12Rich Roll?

  Graphic and social media assets courtesy of Jessica Miranda, Daniel Solis, Dan Drake, and A.J. Akpodiate. Thank you, Georgia Whaley, for copywriting and website management. And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Plants. Namaste.