Finding Mastery with Dr. Michael Gervais - Overcoming Limiting Beliefs | Chip Conley

Episode Date: March 18, 2020

This week’s conversation is with Chip Conley, a boutique hotel entrepreneur who helped Airbnb's founders turn their fast-growing tech start-up into a global hospitality brand.After selling Joie de Vivre Hospitality, the company he started as a rebel entrepreneur at age 26, Chip wasn't sure what was next.He could have retired at age 52 but the young founders of Airbnb came calling.Chip served as Airbnb’s Head of Global Hospitality & Strategy for four years — while also being CEO Brian Chesky’s mentor — and continues today as a Strategic Advisor to the company’s leadership.Chip wrote about that experience in Wisdom@Work: The Making of a Modern Elder where he shares his unexpected journey at midlife — from CEO to intern.While writing Wisdom@Work, Chip was inspired to build the world's first "midlife wisdom school," the Modern Elder Academy, with a 3-acre oceanfront campus in Baja California Sur, Mexico.So why does Chip care so much about this idea of a “modern elder?”It’s because there were a few key points in Chip’s life where something was eating at him… he knew he wasn’t on the right path but it could have been easy to stay the course.Chip made the difficult but necessary decision in those moments to make a change and that’s at the heart of this conversation.This is about authenticity, it’s about being in touch with your core principles, and ultimately, it’s about wisdom.Chip’s seen it from every angle – entrepreneur, founder, mentor, and continues to make an impact on the next generation._________________Subscribe to our Youtube Channel for more powerful conversations at the intersection of high performance, leadership, and meaning: https://www.youtube.com/c/FindingMasteryGet exclusive discounts and support our amazing sponsors! Go to: https://findingmastery.com/sponsors/Subscribe to the Finding Mastery newsletter for weekly high performance insights: https://www.findingmastery.com/newsletter Download Dr. Mike's Morning Mindset Routine! https://www.findingmastery.com/morningmindsetFollow us on Instagram, LinkedIn, and X.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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stay present and engaged with my thinking and writing. If you wanna slow down, if you wanna work smarter, I highly encourage you to check them out. Visit remarkable.com to learn more and grab your paper pro today. I wanted to create a place where people can actually understand a new roadmap of life. We have midlife, which was originally 45 to 65, I think is now 35 to 75 because in certain industries, people feel at mid-30s, they're over the hill. And a lot of people are going to work till their mid-70s or later. And therefore, midlife is a marathon.

And yet, if you're running the marathon with all of your past mindsets, identities, responsibilities, and stuff, you're running the marathon with all your baggage. And what we have to do is create a great midlife edit that helps people to let go of that. Okay, welcome back or welcome to the Finding Mastery podcast. I'm Michael Gervais. And by trade and training, I'm a sport and performance psychologist, as well as the co-founder of Compete to Create. Now, the whole idea behind this conversation is to learn from people who are on the path of mastery, who have dedicated their life efforts towards understanding both mastery of self and

mastery of craft. And at the time of this recording, I've never experienced what we're experiencing nationally and certainly globally. And I'm going to have more thoughts on this later, but just a quick hit is that, you know, for the United States to be on a state of emergency, it's pretty radical, you know, and I just want to put a note in there is that I know people are stressed. I know that times are challenging. And I know that also some people are like, what are you talking about? It's fine. I just want to put a note in here that I'm recognizing and feeling the amount of stress that some of us are under. And I just want to say, stay with it now. And I also want to say, I'm so happy that we're in it together and that we have a community of people that are like-minded and getting after it and have been down the path of understanding how to front load and work with

one's mind to be able to manage high stress and high pressured environments because we're in it. This is a test. How well will you be able to manage the unfolding unpredictable unknown? Now, we just happen to have a collective consciousness right now about what's happening and it's an unfolding pace, like it's an unprecedented pace where information is unfolding. So I just want to take a moment before we dive into the wisdom of our guest today, just how much, if you're struggling and you're lonely and you're isolated and it's, or you're anxious and you're really struggling, stay connected, you know, get into the Finding Mastery tribe, you know, get into, you know, places where you can be heard and felt and be part of something. And one of the inoculations to struggling is to help others.

And I just want to say this right now. You can have your purpose today. You can declare it. It's okay. You can make it up right now that your purpose is to be in the service of others. It's not that hard. You can do it. It's not that hard to commit to it. It's actually quite hard to do. So I'm here for you, you know, in the best way that I can be from, from a distance. Um, and also just recognizing the challenging time that we're in and the whole idea behind these conversations is so that we can learn and so that we can grow together. And we've all got these unique, independent paths. That's one of the reasons I love the Finding Mastery Tribe. If you're interested in, if you're not part of it, punch over, check it out. You can go to findingmastery.net forward slash tribe, totally free, just a community of thousands of us

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but for energy and focus, recovery, for longevity. And I love that David is making that easier. So if you're trying to hit your daily protein goals with something seamless, I'd love for you to go check them out. Get a free variety pack, a $25 value and 10% off for life when you head to davidprotein.com slash finding mastery. That's David, D-A-V-I-D, protein, P-R-O-T-E-I-N.com slash finding mastery. So this conversation is with Chip Conley and it couldn't be better timed, really. He is a boutique hotel entrepreneur who helped Airbnb's founders turn their fast-growing tech startup into a global hospitality brand. And he started as a rebel entrepreneur at the age of 26. And after selling Joie de Vivre, the hospitality business that he built, he wasn't sure what to do next.

And so he could have actually retired when he sold it, as he puts it. And that was at the age of 52. But some young founders of Airbnb called him up. And Chip eventually served as their head of global hospitality and strategy for four years, while also being a mentor to Airbnb's CEO, Brian Chesky. And he continues today as a strategic advisor to the company's leadership. And it's a really cool story. Wait until we get into this.

And Chip wrote about this experience in Wisdom at Work, his book, and the subtitle is The Making of a Modern Elder. And that's where he shares his really unexpected journey at midlife from CEO to intern, basically. And so while he was writing the book, Wisdom at Work, Chip was inspired to also build the world's first midlife wisdom school. And he calls it the Modern elder Academy. And he's got a three acre oceanfront campus down in Baja, California in Mexico. And from the looks of it and the sounds of it, I mean, it's pretty special. Okay. So if we double click under why he wanted to build the modern elder Academy, it's because there was a few key points in Chip's life when

something was eating at him and he knew he wasn't on the right path, but he could have easily stayed the course. So Chip made the difficult decision, but necessary decision in those moments to make a change. And that's at the heart of this conversation. If you are struggling with something or you're trying to sort something out, you know, it's not quite the right path. The how and the why and the strategy behind how to pivot and go the direction maybe your heart wants you to go or, you know, away from what isn't feeling right. And it's really about authenticity. It's about being in touch with your core principles.

And ultimately, it's about wisdom. So Chip's seen it from every angle, from an entrepreneur, a founder, a mentor, an intern, and he continues to make an impact on the next generation. And with that, let's jump right into this week's conversation with the legend, with the modern elder, Chip Conley. Chip, so happy to have you here. Thanks, Michael. It's good to be here. Yeah, this is great. Okay. You have a storied history and as like, I can't wait to unpack and really pull on some threads of wisdom and applied insights, as well as just downright

things that you've figured out that are applicable to many, right? And you've had this really unique path that you've traveled. That being said, I wonder if we could start with a moment in 2013 where you're brought in as the senior elder man of wisdom. The gray hair. To help guide. No hair. gray hair to help no hair right yeah to help guide a company yeah and and i might be overstating the position that you're in at that time but this is airbnb 2013 and you're sitting at a table and you look around and you say whoa what am i like i'm i'm the old guy here with all these

tech geniuses and so can you can you unpack that moment just a bit? Yeah. So I was the boy wonder when I started a company at age 26. And I didn't know what the hell I was doing, to be honest with you. I started a boutique hotel company called Joie de Vivre. It means joy of life in French. And ran it for 24 years. And then sold it in the Great Recession.

It was a tough thing. It was my identity, but I knew I had to move on. And so I did, um, partly because of the financial situation, the great recession. And then two years later, the three founders of Airbnb approached me to help them take their little tech startup, um, because they had nobody in the company with any hospitality travel background or any entrepreneurship background. And so I joined, but I didn't think about the fact that yes, they wanted me to be the mentor, their in-house mentor, and then the head of global hospitality and strategy. But what I hadn't really thought of

was like, wow, I'm 52 years old now. I'm no longer the boy wonder. I'm now like the modern elder, as they started calling me because I was twice the age of the average employee there. And what was interesting for me was the process of right-sizing my ego, having been running a company where I grew it from one person to 3,500 people. But now I'm no longer the sage on the stage of the company. I'm actually the guide on the side. I'm the person who's helping these three founders take their little company and turn it into a global hospitality brand. And what I had to do was really get used to the idea of being liminal, which means to be in transition and to not always be the one who knows everything. And I mean, I was at times the dumbest person in the room because I'd never worked in a tech company before. So the moment I had on my third day is when I realized and got, and had was full of fear. Like, wow, I thought I was supposed to come in here and just help them

with my wisdom. But actually it was my curiosity that was starting to get stoked because I had no idea what a tech company was like. And that was a hard thing because at 52, you're sort of, you sort of feel like you're in your middle of your life and you've built a lot of wisdom. Actually, you built a lot of knowledge. Brian, the CEO, who I still mentor seven years later, he said to me, Chip, we hired you for your knowledge, but what you brought was your wisdom. And I had never heard of any, the difference between knowledge and wisdom, but, but the moment I had was almost leaving the company after my first week, because I was scared that I was going to fail in something I'd never done before. Okay. So on, so help me understand the level of fear at that board meeting or that meeting, maybe it's not a board meeting, but at that meeting on a scale of one

to 10 to make it really concrete, a 10 is like, I feel like I'm going to throw up in my mouth. And a one would be like, you know, this, this is pretty boring. It wasn't 11. I was going to throw up on you. Okay. So you were activated. I was so agitated that after three weeks I went with, on my, with my father for a hike and, um, about 15 minutes into the hike, he just stopped and he

turned around and he looked at me and he said, how are we going to turn your fear into curiosity? And your dad said, my dad said, so this was post the meeting. This was post the meeting. It just got worse after the meeting. So the first three weeks, about three weeks into it, I was saying to my dad, dad, I'm with these guys. They are talking a language I don't understand. And I feel really dumb. Okay, so this is really important for me. So you had a model going into that moment. Yes. And that model was fear-based.

The model was not, yeah, it was fear-based. And it was, to use Carol Dweck's work of fixed and growth mindset, my mindset was a fixed mindset. I was in the mindset that I was always proving myself. My job was to be successful meant winning. And that meant I had to look good. That meant I had to get the answer right all the time, et cetera. And the growth mindset is when you actually are not focused on proving yourself. You're focused on improving yourself. There you go. Okay. Improving was the thing I hadn't really thought about. I thought like,

did you know that framework prior to, you know, I, I had heard of it, but no, I'd never studied her book or read her book. And it's interesting because there's a difference between knowledge and then applying the knowledge. Right. And so now we're starting to talk a little bit about getting to wisdom, but just knowing this is one of the challenges or fears I have about these conversations in this podcast. And it's twofold. One is the amount of knowledge and insight and wisdom that you hold and other guests hold. Am I going to be able to figure out how to apply those in a meaningful way in my life?

Yep. And then are folks listening, are they going to be able to like actually do something with it? Otherwise we're in some respects polluting the, the, the airways of just more bits of information. Or just inspiration. Yeah. Right.

And maybe that's not so bad, but inspiration, meaning breathing life into something, is a beautiful concept. And I have this idea, and I'd love for you to chin check this a little bit, is that I think that we need to hear something or experience something X number of times. I don't know what the number is. But on that final number, that's like, oh, now I get it. And so the, this can't, this come, this insight comes from when coaches would say to athletes, Hey, you got to put it on your inside foot, put it on your inside foot, like soccer, put it on your inside foot. And then it's not until the X number of times does it actually go, oh, I get why.

And I get how, and I can do it now. It's sort of like advertising. You know, if you talk to advertisers, you have to hit them nine times or 27 times to actually have it like, you know, really sink in. Yeah. There's no doubt. And I think the world today is more distracted than it used to be. So in some ways, maybe the repetition needs to be more. So where I was. Or the pain needs to be greater pain needs to be greater because certainly there's no doubt that we learn we're willing to learn

and make change when pain is uh you know in our lives let's go back to the 2013 meeting you had a fixed approach it was ego persevering yeah that's not the right way to say it. It was about ego preserving. Yeah. Yeah. So you're about protecting your ego. Right. And, and you go into the thing and do you feel fear? Do you feel it in your body and in your mind, or is it predominantly one or the other? Both. Yeah. Because some people just have it in their body and some people have it just in their head. So that's cognitive anxiety versus somatic anxiety. And you feel both. it in my brain, which is where the ego piece of it felt. What were those thoughts? Well, I mean, it was like, okay, Chip, you were a very well-known and successful boutique hotelier. And then you sold your company at the bottom of the great recession because you were done with it. And we'll talk maybe a little bit later about, I had a precipitating activity where it led me health-wise to say, you know what? I've done this for 24 years. It's time to do something else.

And if the next thing I was going to do was going to be something I'd fail at, that would be just awful for my sense of self-esteem and for the way I portray myself to the world. I'm a big fan of the Enneagram, which is a personality typing tool. I'm a three with a four wing on the Enneagram, which basically means I'm someone who gets a lot of juice from performing well. I haven't heard someone talk about Enneagram for a while. Yeah. Okay. Um, and so if the good news is I know myself well, so if I know myself well, that allows me to see my patterns. And I think wisdom is really about pattern recognition. So if you understand patterns and can see early patterns or something.

So what I could see in myself was, ah, I've seen this movie before. This is when Chip goes into performance anxiety and I'm not as good as I could be because I start using, my brain gets actually in the way. But it had to be my father who was the one who said, who helped me to take from the conscious, the unconscious to conscious when he said, how do you turn your fear into curiosity? So then how do you make that prescriptive? How did your dad know that? Because curiosity is an inoculation for anxiety.

It actually is one of the preferred and relatively well-studied approaches. How did your dad know that? It's not because he's a psychologist. That's for sure. My dad's sort of an old school captain of the Marines, Naval Reserve, Marine Reserve. But he knows me. He's seen my patterns. So if wisdom is pattern recognition, he knew Chip as somebody who sometimes got his brain

in the way of his ability to do something. Okay. Hold on. God, Chip, this is so good because I want to now understand. I know that we're toggling between 2013 moment and insights that are hovering around that. I do want to stay on the approach, but I want to double click on this thought for you a little bit is how does your dad know you? Cause you grew up in a neighborhood that sometimes it's tough to get out of. Yeah. Is that fair to say? Well, I was luckily in a, I was part of the Long Beach poly high school, number one feeder school for NBA and NFL athletes. Pretty famous. The cover of Sports Illustrated is the best

athletic high school in America. It's ridiculous. The talent there is ridiculous. So I was lucky. We were in a relatively nicer neighborhood, but within that particular district lines for that particular school. I loved it. My father went there as well. It's a school district that has gotten more diverse, racially diverse over time. When you were there, what was this diversity? I was, they called me the curious white boy. So we had about 30% white and the balance was people of color with African-Americans being the largest percentage. What did you learn in high school about diversity? Oh man.

You know, the whole, the whole, it's so interesting to hear the word, the other a lot these days, because I learned what it meant to be the other. I was the other. And I think every white male in America should learn what it means to be the other, because in a lot of environments, I went to Stanford after that. I was not the other in the sense that I was in the demographically majority. So I learned a lot about otherness and the beauty of that. We did not have homecoming kings and queens in my high school. We had international ambassadors.

We had four of them, four times two. A guy and a gal, Caucasian, African-American, Asian, and Latino or Latina. And so this was back in 1975, 1978, which is when I graduated from there. So I learned really early about multiculturalism and how to understand people from their ethnic origins in a way that allowed me to become a much better leader, especially in the hospitality business when the majority of our employees are people of color and mostly immigrants. So, yeah, huge.

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they also help me stay focused for longer without digital fatigue creeping in. Plus, they look great. Clean, clear, no funky color distortion. Just good design, great science. Thank you. You spell it F-E-L-I-X-G-R-A-Y.com and use the code FindingMastery20 at FelixGray.com for 20% off. Okay, so sometimes being the other could lead to you to have protection mechanisms so that, you know, you feel safer being a minority. But you didn't do that. You earned that curiosity white guy label. Yeah. So you were curious about others. I was. Experience. And so did that translate to, did that curiosity translate to compassion and empathy or did it, does it stay purely as a curiosity approach? Definitely compassion and empathy. I mean, I, I'd say there's some parts

of my life where I'm not so compassionate and empathetic. But when I came to people who were from a different background than me culturally, always has it's been died in the wool in terms of how I am. I ended up my first hotel. And when I when I started my hotel company in San Francisco was in the Tenderloin in San Francisco. So I bought an old motel in a bad neighborhood, very much like where my high school was. I got a foster son, African-American foster son, who I played basketball with. And he was homeless because his parents were drug dealers and they ended up in jail. And long story short is it's my upbringing. Did you adopt him? I actually became his foster parent. Foster parent. That's different than adopting. But he's now an adult and he's still, I'm still his foster parent in terms of how he sees me. And he has three kids and one of his kids now actually has

a son. So I am a great grandparent at age 59, but I also have an eight and a five-year-old biological sons. So that's a complicated one, but let's go back to your question. Okay. Well, this is important because it's about family. Yeah. How did your dad know you? You know, it's interesting question. My father, so I'm Steven Townsend Conley Jr. Chip off the old block, Chip Conley.

My father and I went to the same high school. My father was my, my boy scout leader. He was an Eagle Scout. Guess what? I was too. My dad was my baseball coach. I was the star pitcher. I went to the same high school. I swam and played water polo, just like my dad. I went to Stanford, just like my dad. I joined a fraternity, not the same fraternity that my dad was in. This is your big moment. This is my big moment. I broke my big moment. Oh, my God. I broke away. But here's the interesting thing.

Let's keep going on this. So I broke away and I was in a different fraternity, but I studied the same. I got my dad's an economics major. So was I. He ended up going to UCLA Business School. I went to Stanford. But it was in my second year at business school. Actually, it was in my summer between first and second year of business school when I was working for Morgan Stanley, that I had my true break from my father.

My father knew me well, but he knew me as the little version of himself that was going to be more successful than my dad. Okay. So let me just pause for a moment. Does that mean growing up, you were never seen? I was never seen and I didn't want to see myself. And the reason I didn't want to see myself was because from a young age, I knew, and this is an interesting little piece I was going to get to, that I was gay. And the last thing anybody knew about me was that. I didn't want them to know that. In my fraternity days, I didn't want that. Playing Stanford me was that. I didn't want them to know that. In my fraternity days, I didn't want that.

Playing Stanford water polo, I didn't want them to know that. I didn't want my dad to know it. I'm the only son, two younger sisters. I'm Stephen Jr., Chip off the old block. So when I did, so my dad, did my dad know me? Not really. What he knew is that there's this private part of Chip that loved writing and was a bit of an introvert. And it was sort of like a softer side of Chip. But I was a type A competitive athlete,

and I was somebody who was going to go out and be successful because that's what my parents expected of me. So when I came out between my first and second year of business school at age 22, and this was a long time ago, this was 1983, it was not an easy time for someone to come out. It was right in the hysteria of age, just getting off the ground in terms of people knowing about it. When I came back and told my dad that, you can imagine, he just looked at me like, what the hell? This is not who you are. So I went into reparative therapy and I was in for six months, had a surrogate, a woman who was 15 years older than me, who I was having sex with. We're not going to go any further on this one. But what I'll say is at age 22, 23, I had to learn who I was because I had been pantomiming my way through who I was and I'd been doing it really well.

So this is a hard thing. I'd been a success. I went into Stanford Business School straight from undergrad. You don't do that because it's really impossible or hard back then, especially in still. But I was somebody who had to have this identity shift and basically take off the costumes. I was born on Halloween. I'm an October 31st baby. So I knew what it meant to wear costumes.

Chip, my heart is pounding listening to this because the courage. I don't know what it is that I'm necessary feeling right now, but literally my heart is ticked up a little bit and the courage to be you in a difficult climate at that time. Yeah. At the same time to have that radical break and to have this chip off the old block thing. Yeah. And then to know that even in this conversation, you've got the ability to take care of yourself. We're going to, when you said we're going to stop the conversation at this level, I love every bit of it. Keep going.

Listen, I mean, I just don't know if your listeners want to hear it. You know what? You know what? I, yeah, because this is about courage. It's about knowing who you are and dressing accordingly. Yeah. And that dress means that's an old kind of – I do not wear dresses.

Yeah, right. But no, the idea of know who you are, dress accordingly is from one of the Stoic philosophers, which is like do the insight work and then be you. Well, and Oscar Wilde, famous gay man, long ago said, be yourself. Everyone else is taken. Yeah, right. So thank God. I mean, you know, the truth is that I,

in my early twenties, I did have to have the courage. And, but I also had this weird sense that the path I was on didn't feel right. And it didn't feel right in the sense that I don't think I could continue on the path I was on didn't feel right. And it didn't feel right in the sense that I don't think I could continue on the path. I, interestingly enough, what would happen if you did? Well, my parents met at Stanford. And so my freshman year, I met my girlfriend who was very beautiful, beautiful. She was like total marriage material. We went out for two years, but I just could feel like there was an element, like, I don't know if I can keep doing this. And, um, you knew you were gay. I knew I was gay, but I'd never, I'd never had any experiences. I'd never, you know, I'd only, how do you know that you're gay? What does that mean? Um, it means that when I was playing basketball in junior high school and I was a pretty good player. I enjoyed hanging out

in the showers. I just take a shower with everybody else. I was curious, curious white boy. I didn't earn the curious white boy because of, hey, Chip's looking at us in the showers, but I earned it because I was just curious. And I think the curiosity I thought initially was just curiosity in other guys' bodies growing into puberty. And then over time in my teen years, I realized I fell in love with my best friend but never told him, didn't feel any comfort in that. We dated each other's – we both had girlfriends. Our girlfriends were best friends. But I knew it inside but I didn't want to deal with it because I knew the consequences were

so dire. I sort of thought I would like maybe grow out of it, but it was in college where I realized, wow, I'm still trying to be my dad because like my dad met his wife, my mom at Stanford and I've met Lynn and she's amazing. And my parents love her and everybody loves her, except I just don't think i can spend my life on the path that this is on which is basically a path where i'm going to get married and then i'm going to have this i don't know if it's a secret life because i didn't have a secret life at that point and i never did so when i came out i you know i came out when i was like okay now i've had an experience with you know with, uh, with a man and I was like,

okay, yeah, that is more me. I want to know about the tension that you're operating with. Was it a low level hum? Was it a full blown daily crisis? Like when you're, when you're with your, uh, female partner and you know, what was that like on a daily basis? Because I want to understand what led to you saying, ah, this is this. I'm faking my way through this. Well, you know, when it comes to being sexual with a woman, faking your way through is hard. I didn't have to fake my way. But over time, I started to have to fake my way. And I started thinking, what am I fantasizing about?

And that's that is so different than what's going on right here. And there was that, but beyond that, I mean, I truly was, I was never to a place where I was suicidal, but I was definitely, you went to some heavy places, but I definitely went to a place where it was dark enough to sort of say, you know, this life that I'm living doesn't feel like it's the way I, I just, I felt really dark. Um, I don't think I got to a place where I was depressed. I did in college. Oh, wait, you were not depressed. I was depressed. I was, I was not suicidal, not suicidal. Right. Yeah. I'm sorry. And how long was that depression? Maybe a couple of years. Ooh, that's a long time. Um, so, and, and my solution for that was just

to become an admiration addict and the achievement addict and be more and more successful. And you just hit something that I think is at the center of many people that are part of this community. And at the surface level, driven by achievement, which is a dangerous proposition in life at a deeper level, trying to figure out who they are based on what they do. And that necessarily isn't a terrible thing, but there's a potential cost if it's an obsession of the thing that you do, as opposed to really the true investigation of who you are. And so this is like, I need to do more to be more. And that trap is very, very dangerous that you live for a long time. And we still, I mean, I still live it in certain ways. I, the good news is that over time, because I, in my twenties really had to go through a lot of this. I started

to realize that there were alternative paths I can go on. And I started to say, okay, I can be an attainer or an attuner. And there's some sports that are made for attaining and there's some other sports that are made for attuning. Surfing is an attuned sport. Yoga is an attuned sport. Whoa, wait, hold on. I've never heard this because as you're saying that, it's right. Attaining leads to attoning later and attuning leads to feeling at one. And so for me, I started to realize that the things that I need to do, I need to be able to have a lens that tells me, am I in the attain mode? Perfectly fine for certain things, but not fine for other things. Or I'm in the attune mode. And so, yeah, I spent a lot of time learning meditation. Meditation I enjoyed. Yoga,

I didn't. Why didn't I enjoy yoga? Because I was always comparing myself with everybody else in the room. Why did I enjoy meditation? Because I closed my eyes. I couldn't compare. And I could go within. Where did you get that model? A tone?

Not a tone, but a tune. And that's your model. That's me. That's a good model now. Thank you. Yeah, that's a good model now. Thank you, dude. Yeah.

Because I can appreciate both of those. I grew model now. Yeah. That's a good model. Yeah. Cause I can appreciate both of those. I, you know, I grew up surfing. Um, when I was growing up, I thought yoga was ridiculously stupid and I, you know, I was super critical kid and I just thought the whole kind of thing didn't make any sense. And yeah, there's a lot of wisdom and there's a lot of weirdness in that community as well. Like I go back and forth about, um, spiritual narcissism. Yeah. Thank you. You know, like Yogi celebrity thing there, but, but that moment of being able to be connected to your body is a beautiful moment. And then being able to find, uh, the strength and flexibility in your body to be able to sit for an extended period of time to get to the good stuff. Yeah know like there's a deep utility not as a means to an end but a means in and of self

so mastery is all about oh come on the love of practice and the love of practice being it when it comes to yoga the love of practice is definitely an attune thing. It's not an attained thing. And so the love of practice allows you to learn because in the practice of it. So I'm a big George Leonard mastery fan. Oh, you like his work? Yeah. So I was on the board of Esalen, the Esalen Institute in Big Sur for 10 years. So, Oh, you were? And I taught there. Yeah. Michael Murphy was on like, yeah.

Oh, are you kidding? Oh, we, yeah. Like, What a legend. How is he? He's great. He's 88 years old now. He's amazing. He's amazing. I love him. He's a bit of a father figure for me.

Oh, he is. I think he is for a lot of people. And he knows Pete Carroll, right? That's how I met Michael. Oh, yes. That's how I met Michael. It's all coming together for me now. Yeah.

Excellent. So you were there for how long? So I've been on the board. I was on the board for 10 years and I've taught there for 13 years. It's amazing. So that's why you built the Modern Elder Academy. Modern Elder Academy. So Esalen, great example. Esalen started in 1962. And by 1975, there were a hundred personal growth retreat centers around the US. So it became a catalyst for the movement of personal growth. For folks that don't know what Esalen is, just give a quick three line. It's a spectacular piece of land south of Big Sur, California, overlooking the ocean with hot springs. And it's a place where

basically people come to teach personal growth, everything from learning your mastery to understanding your emotions or being in a relationship. It was the epicenter of personal growth developments, spiritual consciousness. It was the epicenter. I don't know if it was the US epicenter or it was global. I think it was global because people were coming there from all over and teachers like Abe Maslow and Stan Grof and a lot of famous people, Ida Rolfe, who started Rolfing was actually living there for a while. And if folks haven't read Michael Murphy's books. Yeah. Golf in the Kingdom. I mean, you know, like I read his books when I was in college and they're massive books. Like you got the Future of the Body. The Future of the Body was the first one I read. And I was like, you gotta be kidding. But it's

like deep and rich and right and deep and it keeps going and going. And if you haven't read that folks that are listening, like, I think it's a, it's a worthwhile investment, but then also understanding Esalen. So you were at the epicenter. I've been lucky, you know, I've, I've been on the board of that institution as well as Burning Man from the founding of Burning Man's nonprofit. And so I love transformational organizations that help people to transform themselves. That is part of the reason why a couple of years ago, I started the Modern Elder Academy, which is the world's first midlife wisdom school. We'll come back to that. Or you want to go there now?

No, let's come back because the fertile ground that we have right now around you figuring out you and the courage to do that is required. Vulnerability is required, but skills are also required to manage that vulnerability. And sometimes what happens for people is that pain is the reason we change. And it's an axiom that I'm going to stand on the table for until I understand it differently. But you had enough pain to change. But also some people have that pain but don't have the skills to navigate the next step well. And it's really hard. Some of us do have the skills to be able to manage it.

And it's a bit of a more of an accelerated arc, if you will. Or we have a teacher or a coach or a therapist that can walk through the next steps with you, right? It's like a borrowed skill set. And so did you have a therapist? I had all of those. I had a therapist. I had a somatic massage therapist. I had friends who were open to going deep with me. Tell me about your friends. Yeah. Because I grew up in an environment where it was a lot of diversity, my friends have always been diverse. So that was one of the things that was helpful for me in terms of coming out as a gay man. But I think whether it's racially diverse or just as someone who went

to Stanford business school, it was funny. I was surrounded by a lot of other type A people, but my best friends were often poets and artists and writers. And frankly, here's a great example. I love writing, Michael. I love writing. But at age 13, I had this feeling like my dad said to me, writers are either poor or psychotic or most or both. But what he didn't say underneath that was like, writers are effeminate, which he did say. I heard him say to my mom once, and there was an element like, okay, I can't be a writer. So in high school, I took English AP and passed out. So I mean, I didn't have to take English in college. Not only did I not take creative writing, I took no English, not literature, nothing. Isn't that amazing? Hold on for this for a moment. Like the subtle

non-conscious installs that people give us. And it can be people that we care about or people on the street that just kind of are passing by saying, hey, you don't look good in purple. And we adopt that for the rest of our life. Or not even that you don't look good in purple. And we adopt that for the rest of our life. Or not even that you don't look in purple. It's like they, someone's having a bad day and they just sort of look at you wrong. And you think it's all about purple. Yeah. Right. Yeah. Man. So that shaped you. It did. My twenties, you know, was a tough, it was a tough decade. When I think back, because I was sort of on an accelerated path, I did have some guardrails of friends and a coach and a therapist. But I started my company at that time. So the reason I called it Joie de Vivre, means joy of life, was because not only was it the mission of the company, but it was what I was aspiring toward.

I didn't necessarily want to aspire toward just performance anymore. I wanted to create an environment where we created Joie de Vivre, including for myself. And that was, I mean, of course, a terrible name. No one could spell it or pronounce it. And most people didn't know what the word means. But it meant a lot to me. Do you have French origins? I don't.

No. In fact, at Long Beach Poly High School, I took French, not Spanish. Sort of silly in Southern California because it's like Spanish-speaking people all around me. But one payoff of taking French in high school was the name of my company when I started at age 26. And it became the second largest boutique hotelier in the U.S. Finding Mastery is brought to you by Cozy Earth. Over the years, I've learned that recovery doesn't just happen when we sleep. It starts with how we transition and wind down. And that's why I've built intentional routines into the way that I close my day. And Cozy Earth has become a new

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That company, Joannevieve. So now it's a Hyatt company. It's owned by Hyatt, but I sold it 10 years ago. They know if you were in California and especially Northern California, you might have been familiar because we created 52 boutique hotels, tons of them in the Bay Area and San Francisco. We had 21 boutique hotels in tons of them in the Bay Area and San Francisco. We had 21 hotels, boutique hotels in San Francisco alone at one point. So hotels like the Hotel Vitale, which is on the waterfront right next to the cross street from the Ferry Building. That's a building

we built from scratch. But my first hotel is called the Phoenix. It's a rock and roll, funky motel in a bad neighborhood where all the musicians coming through town come to stay. And that was my first hotel, which against all odds, it was a pay-by-the-hour motel that I bought and raised a million dollars to buy it and renovate it. And like on a shoestring, it opened and became a big success. So- When I hear pay-by-the-hour, I'm thinking like people are turning tricks. That's exactly what it was. When I bought it. No way.

When I bought it, that's exactly what it was. Oh, so you didn't turn that into it. No, I didn't. On a bad week. I thought maybe we should go back to it, but no, no. Okay. It was a no tell motel when I bought it. No tell motel, meaning you go there at lunch, the lunch hour.

Wow. Look at that. Okay. So let's go, let's go back to this idea of your friends for just a moment. Is that what kind of conversations do you have with your friends? Deep. Deep and funny. Someone at one of our recent Modern Elder Academy workshops said, I like deep and funny people.

And I was like, oh, God, I wish I could have said that. I like people who have gravity and levity. I'm right at that intersection. Gravitas and levity, I'm right. I'm right at that intersection. Yeah. And levity, which is sort of an interesting combination because one of them speaks to heaviness and depth and the other speaks to lightness. And I think being able to being a modern elder, being wise is knowing when to up the ante on one versus the other,

just like curiosity and wisdom, um, are sort of like a nice, there's an alchemy between the two of those two. So I, uh, my friendships are generally with people who want to go deep. If you don't want to go deep, like a lot of people I know, then you probably don't like hanging out with me quite as much because I'm going to ask you questions you don't want to answer. Um, and it's, and, and I'm going to talk about stuff that might be hard to talk about. What are some of your favorite questions to your friends and to people? You know, why are you here on earth? I mean, that's always a tough one. And why questions can actually be awkward too, because they can sound like you're sort of

preaching a little bit. I think the questions I like to ask are questions that are based upon something called appreciative inquiry, which is a method of asking questions that opens up possibilities. So they're empathetic questions. They're thoughtful questions. The question is meant to serve the other person, not necessarily just to serve me. So an example of an appreciative inquiry question would be like, you know, what gets you really turned on about imagining five years from now in your life? Like what is, what is it that most sort of like gets you jazzed and juiced up? Um, and then what are we doing today to help you get there? And I mean, that would be one way to pose a question that sort of is aspirational and

hopefully prescriptive as well. Also concrete. Yeah. So are you more aspirational or more concrete in the way you approach life? I think, you know, it's just like everything else. I've just said wisdom and curiosity. It's like that duality. It's gravity, gravitas and levity.

It's, it depends on what is needed right now. So, um, if concrete is what's needed now, that's where I'll go. Um, I tend to enjoy, I get more in the flow to use a Mahali Chiksetma high word. I get in the flow a little bit more when I'm in the visionary place. Um, I, I like that. Uh, but I, um, whether it's been at Joie de Vivre as the CEO of that company for 24 years or at Airbnb for the last seven years or at the Modern Elder Academy, I am that weird leader who can be visionary, but also go like, like the Eagle or the vulture that goes from way up in the air and, and just speed to the ground and can get into the weeds if I need to. So I like both. My risk in being both of those things is burnout. And so I have to know that that's the thing I have to keep an eye on is being able to be both of those things means that I tend to be a little too immersed in the things that I'm passionate about. And I think you could have one of three relationships with your work. It's a job, a career, or a calling. And when you have a calling,

there's a, you know, a very high threshold for pain. And it's actually interesting. The experience that led me to selling my company was I had a broken ankle. So my first mentee, the first time I ever mentored somebody was a guy named Gavin Newsom, who's now the governor of California. And he's a very good friend. So he was at age 35 for me, age 28 for him. He had a hospitality company called Plump Jack that he'd started. His sister wanted me to become his mentor. So every Friday we'd hang out and I'd mentor him in Union Square in San Francisco.

Then he became a board of supervisors at San Francisco. Then he became mayor. Then I became sort of his conciliar. I was the guy who came to his office every Friday afternoon to help him while he was mayor. So he was getting married in 2008 and he was having his bachelor party at AT&T ballpark where the Giants play baseball. And so we got to play baseball under the lights, just 20 of us. And I slid into third base and I broke my ankle, but I didn't realize that I had, uh, I'd cut my leg. And so a week later, when I was at his wedding, I had a septic leg. Um, and which means my leg was about twice the

size of a normal leg. And I was, they were going to amputate my leg. And instead they put me on a strong antibiotic. And long story short is a week later, I should have been at home with the covers up over my head. Instead, I was in St. Louis giving a speech on crutches and a strong antibiotic. And I had an allergic reaction to that. And when I was signing books, I went unconscious. But then I actually went flatline. While you were signing books?

Yeah. So I was 47 years old in a city I didn't know and I barely knew the people I was giving the speech to. And I ended up flatline where the paramedics had to have the paddles out to bring me back to life. So I was 22 and a half years again where I felt the handcuffs of my identity of being, you know, of an identity, the identity that was holding me in the golden handcuffs of being the CEO. And, you know, I was like the little mini Richard Branson for this company that was the, by far the largest independent hotelier in California. So you were a rock star. I was a rock star and I was writing a book.

I'd written my third book. This was the book called Peak, How Great Companies Get Their Mojo from Maslow, which I wrote at Esalen. That's cool. Interesting. Nice work. And I didn't know how to get out of this prison I'd created for myself. So you're there again. I'm there again.

This is the second time. Or maybe third time. Yeah. Identity. I had to like, let go of this version three that you're struggling. I think it's probably version two. This is version two at this point. Okay. And so that night in my, uh, I was gonna say my hotel room, but now a hospital room after having been shocked to life, not a bunch of times, nine, nine, nine flatline experiences in 90 minutes. Do you remember when you passed out and you went down? Yeah. I remember what it felt like on the other side. So, and I've actually meet there's like, there's groups of us who meet and talk about it. Yeah. Okay. Are you talking about near death experience? Yeah. Yeah. Yes. What do you remember about going down, being down and then exploring the other side? Because I've been fortunate enough to spend some time with some NDE folks and it's complicated.

It is. And it can be almost scarring. It's so jarring for people to experience it. And I don't know if that was your case. There's a festival in northern Spain called the Pilgrimage of the Near-Death Experience. My experience went as follows. I completely lost track of time. So you have no sense of time when this happens. And the reason I know what I saw was because each time I'd come back, there was a woman who was holding my hand. And she's the woman who booked me this speech. And she was with me through, she was there in the emergency room with me. Ultimately a nurse was the person I just said this to. So every time I came back, I'd say,

here's what I saw. And finally the nurse, after about the fifth time he's saying it, it's like, you keep telling me the same thing. And so I said, write it down for me. I want to make sure. So basically what I was seeing was this. I was in a mountain chalet, spectacularly beautiful, clear skies, sun, you know, coming through a sunlight in the living room, catching the floor. The floor was a really, really, really rich dark wood floor. And there was oil for some reason, a very thick viscous oil on the floor and so the sun was coming in it would actually uh ricochet off the ground and the oil and there was a kaleidoscope on the wall like a colorful like just beautiful all these colors on the wall

just that were being you know from the air from the sun coming in and hitting the oil on the ground. And the oil was then going down some deep, some stairs and the stairs down to, I guess, a basement or something. And it was going like really slowly. So the, the, the oil was dripping down the stairs. So what I remember from that was it was beautiful. It was just exceptionally beautiful. There were no people there, except I was just witnessing it. It's like I was in the air witnessing it. And what I felt from that was the sense of patience, which I don't have a whole lot of, the sense of time, the sense of aesthetics and beauty, which was sort of like just an awe-inducing kind of experience just to see the colors on the wall. And there was a frangipani, like a tropical scent on the oil too. So it just felt like a very sensual experience.

But more than anything, it felt like life was meant to be more spacious and slower than the life I was living at that time. And so I came to that night and I wrote this equation because I had been reading Man's Search for Meaning, Viktor Frankl's book, and I wrote despair equals suffering minus meaning. And suffering is like the, you know, if you're a Buddhist, it's like the first noble truth of Buddhism. We're all suffering. Ever present. We're all suffering. okay, dyspareic with suffering minus meaning, in a really difficult time, how am I going to find meaning? And during the next two years, it was a very difficult time. The Great Recession, a bunch of stuff was going on that was just bad. My foster son was racially profiled and going to San Quentin, let out eight months later by a federal judge who said he's not guilty, but he was scarred by the experience, et cetera, et cetera, et cetera. So long story short is I, every week, every weekend, I would write in my wisdom book.

I created a wisdom book. And I created it actually when I was in my 20s. But I stopped writing in it for a little while. And then I came back to it at this difficult time when I was going through pain. And my wisdom book was, what did I learn this week? And it was particularly valuable in a week where I was having a lot of painful learning. And I would try to actually take what I was learning and turn it into something that could actually be valuable in the future. And so, um, for those two years in the process

of actually then selling my company and getting rid of that identity that was, um, that was in some ways killing me, um, I would write these, these wisdom me, I would write these wisdom books. And I still write that wisdom book now. Is it a weekly journal? 12 years later, yeah. I try to do it every weekend. What did I learn this week? So it's like a post?

It's just like, yeah, it's sort of like a journal, but it's a journal with a point to it, like bullet points of like, what were some of my key learnings this week? How do you reconcile the neuroscientist that says, Oh, NDE, well, you activated this part of your brain and suppress that part of your brain. And so you had, um, a very explainable, um, neuro chemical exchange in your brain and neuro activated, um, experience that is very different than waking consciousness.

It's not the other side. There's no such thing as a spiritual thing. This is just, you know, the pineal gland going a little wacky. Or the vagus nerve. And the vagus nerve is like... Yeah, the vagus nerve is what actually activated it for me, supposedly. You know what, I'm... The wandering nerve. Yeah. Which is a very complicated network of, you know. So how do you respond to that?

That's above my pay grade. I don't know how to respond to a scientist who would tell me that. What I can say, and I think this is true of everything in life, including religious and spiritual experiences, is I'm not here to argue right, wrong. There's a mystery in life. What I'm here to do is to tell you how does it affect me moving forward? There you go. And that's my response. And my response is, that was a divine intervention. It was a hotelier wake-up call. I don't need to be in the hotel any business anymore. I need to sell my company. I need to figure out what's next. Robert De Niro in the movie, The Intern, said,

a musician doesn't retire, they quit when there's no more music left inside of them. And so I knew there was music inside of me, but I needed a different venue in which I was going to actually be singing the music. So what would you recommend to folks? Like, I mean, you've lived a full life, like we talked about at the top here. What would you recommend to folks who are, let's pick any one of the notes that we've talked about that are, let's say depressed, that are struggling with despair. Yeah. And I think I know what you would say, but I won't change my opinion, but I'm really curious what you'll say.

I mean, the last thing I should do is be try to diagnose somebody. So I think that if you really truly are depressed, you should be seeking out therapy as a first step. And then, you know, know that if you have a good therapist, they're going to tell you if you need to be there or not. But I would say one of the things that depression tends to do is it means that you feel disconnected from everything. And you feel, for me, I felt a heavy blanket on top of me. And so there's an element for me of knowing that trying to foster connection to something, even if it's an animal, or it could be a family member, or it could be a family member or it could be nature, anything that's going to just allow you to feel some connection. And that just might be moments throughout the day. And it's really tricky. It's a very tricky

thing because the neurochemistry is off. And when you see the thing that once brought you love and joy and peace and connection, no longer does. Yeah. It's a bit of a, yeah, there's a sense like, oh, wow, is my life narrowing? Is it, you know, it's the, the walls are closing in. So I just think, you know, and also trying to bring back into your life, the things that bring you joy. Of course, that word means a lot to me. And J.D. Salinger wrote Catcher in the Rye said, happiness is a solid and joy is a liquid. And I believe that's true. Happiness and joy are two different things. Joy is something that's bubbling up from inside

of you. And so figuring out where do you find joy and trying to put yourself in environments where you're able to have that. And, you know, if you're in a job that is joyless for you and actually leading to the depression, you know, at some point you may have to leave, but let's just say, okay, you have to, you have to slog through it. Fine. How do you find time on weekends and at nights to do something joyful and, or something that brings you in the flow? Let's talk about flow for a moment. So Mahali Chikset Mihai, who's a buddy of mine, we call him Mike. So Mike Chikset Mihai is the guy who created or popularized the idea of flow.

A few years ago, I wrote a book called Emotional Equations, where I took my despair equals suffering minus meaning equation and turned it into 18 emotional equations. I am an armchair psychologist, driving without a license. But I do have an honorary PhD in psychology. That counts, right? Yeah, I guess. Long story short is one of the chapters was going to be on flow. So Mike Chiksatmehai invited me to Montana to his little cottage with his wife for three days to talk flow. And the thing I learned about Mike Chiksetmehai is the following about flow.

That flow is about, it's almost like, actually, I'm going to go up here to the board for a second. Is that okay? Yeah, yeah, yeah. Let's draw. All right. So here at the board, I'm creating an axis to axis here. One is the y-axis, one is the x. On this is challenge, on this axis is challenge, and on this axis is skill. So, challenge and skill. When you're in flow, what happens in flow is you're between these.

It's often something that's like right up the middle, like 45 degrees. But the thing that he taught me that was so interesting is he said, in order to actually get into that flow, you have to be comfortable with going challenge, skill, challenge, skill, challenge, skill. It's like you go up and then you plateau a little bit. So it's like there's a flow zone here. And the flow zone is sort of in between these two things. But the way you go into the flow zone is like. Now here is interesting.

If you actually combine Mahali Chit Satyamahit's theory on flow, so just write that right there, and you combine it with Carol Dweck mindset, a growth mindset creates a thicker flow channel. A fixed mindset means you're just, you're not gonna be able to go, you won't actually be able to go and do this stair step thing because you've created a narrow channel

so you're so focused on proving yourself that you aren't willing to try the challenge. By the way, this is anxiety up here and this is boredom down there. So I love the fact that this is the kind of stuff we do at the Modern Elder Academies, help people to understand, wow, the theory of flow and the theory of mindset, you create a growth mindset, you give yourself more of the opportunity to potentially get into a state of flow. And being in a state of flow, especially if you're depressed, is as good as it gets in terms of something that actually could help someone to out of that depressed state and more into a state of feeling alive. You know, Joseph Campbell,

famous heroes journey guy said, people aren't necessarily looking for the meaning of life. They're just looking for the experience of being fully alive. And when you're in flow, you do feel that sense of being fully alive. Complete. Well, there's, there's levels of flow too. So high flow, low flow, high flow, meaning like complete absorption. Low flow is like, I'm in and out. It's good. I'm in and out. It's good. Like I'm working. The struggles are less than, um, the sub state of flow, but it's really good. And so there's low flow, high flow is the, is the, one of the insights that I have around this. And I love what you just did with mapping two different theories together. And one of the things that I've also paid attention to

is fear and risk and danger. So I spent a lot of time in consequential environments that those can be incredible triggers for anxiety or incredible triggers for aliveness. Yeah. Right. And so the upside of stress, right. But without, if you don't have the skills to manage that or love that, then it gets really tricky. And if one's purpose is to avoid pain, avoid anxiousness, avoid stress, avoid challenges that challenge one's identity, to your point about fixed versus growth approach. If the challenge is one of identity, then we become exposed and it's too dangerous. And it truly is a fight or flight for one's life as opposed to an opportunity to test skill. Yep.

And so like, well, I mean, this is a foundational theory for me for sure. Flow and, and chicks at me, Holly and Steven Kotler are familiar with some of his work. Yeah.

And Jamie and Jamie. Yeah. So he pulled on some of that in a, in a really cool way. And all that being said is that you went from this thought about if somebody's struggling, go get some help, build a community, you know, that are, that have been down the path and understand it and then see if you can find some sort of connection. And if you find some connections, maybe you'll find that you'll start to love the challenge of finding the connection. And then you'll start to realize that you actually do have the skills.

And if you don't have some of the prerequisite skills of managing yourself in a moment, go get those skills. And so there's two approaches to psychology. I'm going to oversimplify a very beautiful and complicated science. There is, and this is the applied side, there's the discovery approach, which is like, who are you? What are you doing here? Like, what's it like inside of you? You know, all of the stuff that we've been talking about that you've been exploring your whole life. So let's call it the discovery approach.

And there's also the skills approach. and the skills are sets and reps. I mean, like literally just like physical training, you can do mental training, sets and reps, minutes sitting on your pillow, sets and reps. Some of those minutes, you know, of mindfulness training are low quality and some are really high quality. And the high quality means that you're just kind and compassionate to yourself. And you're working by refocusing and exploring without judgment. Those are high quality sets and reps and same with breathing, same with self-talk, same with imagery, same with, same with, same with. So are you more interested in the sets and reps or are you more interested in the discovery? And I think you're going to say the blend of both. It's sort of the theme of our conversation, right? Yeah. Yeah. I mean, I would say both. You know, where do I get my juice? I get the juice. The discovery piece is interesting to me. What's not interesting to me is just to go into psychotherapy. Naval staring. That's right. Yeah.

You know, I've tried actually. It's like I did all that in my 20s. It doesn't mean I couldn't still have interesting revelations. Yeah. The point is to what aim? That's right. So the revelations are helpful when they come, but the, you know, trying to get blood from a turnip, I'm not sure it's all that valuable.

So the habit, I ensure the habits and the practices. Um, yeah, I do, but yeah, pull on that. Like what are some of your more meaningful ones now? Well, I mean, just meditating, having, you know, I've, I've had lots of different styles of meditation or types and practices. I tend to do a TM. I attended to gravitate to TM today because frankly, it's the simplest thing for me to do. Is it a two twenties or one twenties? It's meant to be two twenties. It is sometimes a 10 and a five or it's a 10. That's it. This morning it was a 10 this morning. This evening I'll probably will be able to do a 20 because I have time. The thing that actually I really appreciate, so I love silent meditation retreats. One of my favorites is I get with a guy named Mark Coleman who wrote Awake in the Wild, and it's in Loretto Bay down in Baja. And it's a week long kayaking retreat from island to island

where you're silently, everybody's silent and you're basically kayaking with whales and camping out a week of silence. So if I'm going to do the first thing, the discovery piece, that feels like the discovery could happen out of that because it's in a pretty extreme, and it's not so mentally based. It's, it's like the discovery may come from putting myself in, in that kind of, um, circumstantial, what'd you call it? Circumstantial, consequential, uh, environment, because, you know, that's not easy. Um, and you know, my, um, movement yeah has been around for thousands of years as well and so the paying attention on purpose to the thing tai chi yeah tai chi yoga my 20s walking you know all that i you know i haven't talked about this but i've talked about that i did an i did an ultra

event last year where i did yeah so it was a stand- paddle from Catalina Island, which you're familiar with to Redondo beach and 30 miles. But the first, yeah, it was, it pushed me right to the edge. How long did that take? It was supposed to be six and a half. It's like eight and a half, like full hallucinations. It was, I was a mess. How are your abs? Yeah. And so, um, the point I wanted to get to though, was that, um, the first 10 minutes, I'm sorry, the first 10 miles were gratitude meditation. So it was a, it was a mix between gratitude and, um, silence. Right. And just like really focusing on the sounds and the feeling. And I, and it actually got me in trouble because my speed, my target speed was about 4.3 miles an hour. Like that's where I could go for some time, but I was in

such a flow state. I was, I was moving at about 5.1, 5.2 miles an hour. So it ended up catching up to me at about mile 26, where I was completely out of resources, like internal resources, like physiological. And an interesting dilemma for me to wrestle with as a performance psychologist is that I was in such a great state that it actually pulled me out of the tactic, which was required, the strategy, I should say, required for success. You have to be able to look at your fuel gauge. I got lost. And you didn't have an eye on the fuel gauge. I didn't have a feedback loop. Yeah. External or internal. Yeah. That's a good, well, so what you just described there is the classic challenge for young entrepreneurs. Yeah. Let's go there because I'd love to know

what you have to say to this generation of entrepreneurs and whether they're young or not, but like what's happening now in business. This is, um, I have six CEOs that I mentor right now. Um, and four, four or five of them I've invested in the companies and one's Brian still at Airbnb. Um, what, where this is relevant to what you're talking about with your paddleboarding from Catalina is that if you do get into the flow state and you are so distracted from reality by what you're doing, and you're sort of just in that sense of obsession that a calling can bring, you do lose track of the reality of what's going on around you. I mean, it's not a terrible thing. In could actually have, you could, in certain cases, you could be absolutely hyper aware, which is that beauty of when you're so in the flow that you're just hyper aware of everything, but you're able to take it all in. And that's, that is actually the feeling

I had when I had my near death experience is I felt hyper aware. Um, metacognition, metacognition and losing track of time. So, so where. So where you lose track of things is like things that are mental. What's like the Jill Bolte-Taylor's TED talk about her stroke of insight is you're so in the right brain that you lose track of measuring and things like that. So one of the things that I've seen with young entrepreneurs is they think everybody else is on their same endorphin high or their same – or not endorphin high, whatever their flow high is. And so they think everybody else is on that same thing. Well, not everybody is. And some of those people have obligations and responsibilities that you don't have, whether it's family and kids, et cetera. And so the classic situation

is they are in the process of burning themselves out and they have no clue. I have one particular entrepreneur every six months or so he ends up in the hospital and he ends up having to be, have like, you know, vitamins, you know, what, what is it? Like the IV, the IV, he's become sort of an IV junkie for – and there's some beauty in that. But if you actually get to a place where you know that your pattern is you burn yourself out and then you have to go to a hospital, not just to go to see an IV doctor every few weeks as just a supplement. Instead, it's sort of like it's the peak in the valley. Then you need to actually see the pattern recognition in that so the thing that i try to help younger entrepreneurs with first of all the

number one thing i try to work on is because i've had to deal with it myself is you you're you are not your identity in this job you know i remember the first time someone asked me not first time but one of the first times that someone asked me after I'd started my hotel company, like, how's everything at the Phoenix, my first hotel? I'm sorry, I didn't know what they asked me was, how are you doing, Chip? And I said, everything at the Phoenix is fine. And that friend of mine said, no, I asked, how are you doing? And this idea that our sense of self-esteem gets so attached.

I had five friends commit suicide during the Great Recession. All of them men, between 42 and 52, three of them entrepreneurs who had completely connected their sense of who they were on earth with the fortunes of their company. It's part of the reason, frankly, I created the Modern Elder Academy because, you know, midlife suicides are up 50% compared to the year 2000. So the thing I try to do with the entrepreneurs is to help them see first and foremost, you know what? There are a lot of, there's a lot of reasons that a business succeeds or fails that have nothing to do with you. And so let's start just knowing that. And it's, this's not life or death.

And then secondly, help them to actually see that depending upon the business they're in, most people are running a marathon, not a hundred yard dash. So how do you help people to sort of realize that the pace that they're on and the pace they're expecting everybody else to be on is going to lead at some point to poor performance. Um, it, it may actually lead to heightened performance. Fear is a great motivator for a hundred yard dash. It's terrible motivator for a marathon. And, um, so that we go into that, then help them to understand it's who, what are the resources you have available to you beyond yourself? Because so often what happens is they take on too much. And so then it's a matter of like, okay, how do we start to look at, first of all, with

Brian and with Airbnb, let me just be honest. I had to say, we have 30 strategic initiatives back in 2013. We need four. And in the next four months, we, as the founders, as a founding group, three founders, plus our, uh, our leadership team, we're going to come up with four. And we did, you know, we did a three, three day retreat. And when you iron those four out, right. And that's, that's hard intellectual work to choose. What do you do? Like, what is the, what is the tactic to support those initiatives? Like, and I'm thinking like super block and

tackling right now. Like, how do you write a strategy? How do you write the objectives? How do you know how to do that? There's a science and an art to this that is a little lost on me. Well, the first start, the first thing was getting clear on, you know, using some Stephen Covey stuff about urgent and important, you know, doing a two by two quadrant and say, okay, what, what, what's, what's, what are we doing? We have some initiatives here that are not important and not urgent. Why are we even, those are the, in the 30, those go away immediately or will they go into a parking lot? Because in some, some cases they're pet projects, but they're, but they're not urgent or important.

So I think getting to the place, first of all, where you prioritize and you have a nice mixture. I think for any kind of business, it depends on where they are in their life cycle. The earlier you are in your life cycle, the more you have extreme focus. You just have to have extreme focus because you got to... Does that mean you don't pivot at some point? No, you can still pivot, but focus and then pivot. Don't focus and pivot at the same time because focusing and pivoting at the same time means you're not committed fully to the first thing. And you got to commit. I mean, it's like anything you have to commit to

the first thing, do it. And then if it's not working, go to the second thing and know that it's good to have a second thing to go to. The, you know, the challenge for a lot of entrepreneurs, you know, is like, is it time for us to go to the second thing or do I keep going on? And that's a, that's a one I can't answer sort of with a generalization, but the blocking and tackling speaks to like, okay, it's pretty simple. You know, who's, you know, what defines success? What are the KPIs, the key performance indicators? Are we all aligned that those are them? And that's frankly, usually in a lot of companies, one of the biggest challenges, everybody has a different definition of success. Once we get the KPIs right of what's important, then okay, who, what are each

of us doing to impact that? And how are we monitoring that on a weekly basis? And in many companies, they do a huddle daily to use a little sports terminology. And it's a morning huddle, especially in tech companies to sort of say, okay, what are we all working on today? And by the end of the day, what do we want to have gotten accomplished? I love it. Is that like a 10-minute? Yeah, 10-minute meeting at the start of the day, what do we want to have gotten accomplished? I love it. Is that like a 10 minute? Yeah. 10 minute meeting at the start of the day. And it's, you see it with product teams in tech companies all the time. I'd never had any experience with it in the hotel business. But actually in the hotel business, more and more, you're seeing it, especially when they're

doing big events. You have a huddle at the start in the morning and before the big event, and maybe a huddle at lunchtime to say, where are we going? How's it going so far? How do we need to pivot for this event? And, uh, and then something at the end of the day to, to, you know,

look at lessons. Coach Carol, the Seahawks meets every day, first thing in the morning with his coaches, they all have a moment to kind of get their stuff together and get an idea for the day they meet. It's a 10 minute kind of, um,

tone setting, um, issue raising moment. And then, you know, and they meet throughout the day as well, but it's a moment at the beginning. It's a 10 minute kind of tone setting issue raising moment. And then, you know, and they meet throughout the day as well, but it's a moment at the beginning. It's a, it's a coach huddle. That's what you're talking about that happens. And so you would do that with the executive team as well. Yeah. I think you do it.

We tried doing that at Airbnb with the executive team and it was hard. We did it for about two or three years at some point because people were on the road so much and people were trying to call in and then, then there's the years. At some point, because people were on the road so much and people were trying to call in and then there's the distraction of like, oh, they're not on yet. And it's like, no, this is supposed to happen quickly. A huddle is supposed to be like a 10 minute thing. Or maybe up to a half hour if you're going through a particularly difficult time. But it's meant to be just a check-in. But it also is meant to be substantive, which sounds strange for 10 minutes. But it is substantive in the sense that it gets people in the same room meant to be just a check-in and, but it also is meant to be substantive, which sounds strange

for 10 minutes. Um, but it is substantive in the sense that it gets people in the same room. Uh, and then the conversation that happens afterwards between two people who actually needed to talk is going to happen at the start of the day. And so what that 10, let's say that 10 minutes, is it something as simple as like, what are you working on today? Yeah. Each person goes around and says, here's, here's my priorities for the day. For the day. Yeah. Super simple. Real brief though.

Yeah. Right. You don't, you don't go through your, like, I meet with this person at eight o'clock, eight 45. And then this person, no, it's like top three, maybe top three key things that you're trying to accomplish that day. Yeah. Really cool.

Okay. So back to the wisdom piece is what do you, how have you developed wisdom? And it's a really big question. And I don't know if there's an answer to it, but you have it. I can feel it like the clarity of thought that you have and the groundedness in your approach and this, the sensitivity to the nuances of things and the complication of things that life is multidimensional, multifactorial, and it's organic and living and breathing. Like you have the sensitivities to, um, the human experience on an ecosystem that's, uh, always changing. So like how? Well, so that wisdom book I write in on the weekends helps. I think more than anything, wisdom is about pattern recognition. So the question is, how do you accelerate your process of recognizing patterns? And I think for me, I'm with myself 24 hours a day. I don't

have a choice. So recognizing my own patterns is I should be the expert in the world on Chip Conley in terms of how I tick. Now, the funny thing about us as humans is I'm usually better at telling my best friend how they tick than I am about myself because I have the objectification, you know, which I saw 12 years ago when I saw, oh my God, I'm dead here. I'm like, I don't have a, and I could sort of be in a room and see, I didn't see myself in that room when I was, you know, near death experience, but I could see with an objectification of what's happening right here. I did actually, I was able to see at one point when I was in the emergency room, the doctors above me, you know, trying to actually

pulling the paddles out. So I could see that that was something I didn't see even when I had no, no heartbeat. So I think being able to be brutal and beautiful in objectively witnessing what is happening in terms of your own life is a first piece. And so I think that's why having regular check-ins with yourself, maybe every weekend of what did you learn this week is, is a shorthand way of making sense and creating meaning out of what's happening in your life. And then taking it prescriptively forward, it allows you to say, okay, in the case as a leader, what it allowed me to do is to start seeing the patterns like, wow, for four weeks in a row now, I have written about this one particular direct report of mine and the fact that I just don't have confidence that they are having direct conversations with that person's

direct reports. And I feel like there's a disconnect because when I talk with their direct reports, I feel like they are lost as to what's going on. And the conduit here is that person who's my direct report. Part of what I've learned in my life is I was Mr. Can Do It. The book I gave away to all of my employees, like 3,500 of them at one point, is like the little engine that could, that children's book. So my whole voice in my head was always, can do it. I can do it. I can do it. And in fact, our company, the number one metric we used for our employee, whether they're doing their job well, was did they square well for can do it attitude? So I was all about can do it. I'm now on a stage in my life where I'm a

conduit. And that's the big difference, a can do it to a conduit. And that change is when you realize that you have shifted your operating system, your primary operating system. You mentioned that term earlier. I said I'd come back to it. The primary operating system from adolescence to middle-essence, and middle-essence is mid-life. It is basically when you have hormonal and emotional and physical changes between 45 and 60, the primary operating system is your ego. And then the primary operating system around middle essence becomes the soul. But we have absolutely no maps of life that help people to understand you're on the road at age 52 or 48 on the metaphorical road of life. And here are some signs on the road to tell you you're about to change your operating

system. And so instead, what we have is circumstantial things that happen in people's lives that shock them into the pain and suffering that maybe makes them make a change, but absolutely not have the kind of language I'm talking right now. Unless, frankly, it's religion or spirituality that they go to and they start talking that, but no one talks about the fact that there's a, there truly is. I think Carl Jung said this very well in many different ways. You move from that, you know,

operating system of the morning to the operating system of the afternoon or evening, and it's a different operating system. And in many ways, my experience at Airbnb took me out of chip the ego, the sage on the stage, to chip the conduit who is helping these guys make their company successful. And that was circumstantial way without pain, other than the pain of feeling the fear of like i don't know if i can do this to start realizing wow and that's what ultimately led me to create the modern elder academy is like i wanted to create a place where people can actually understand a new roadmap of life we have midlife which was originally 45 to 65, I think is now 35 to 75 because in certain industries, people feel at mid thirties,

they're over the hill. And a lot of people are going to work till their mid seventies or later. And therefore midlife is a marathon. And yet if you're running the marathon with all of your past mindsets, identities, responsibilities, and stuff, you are not running the marathon. You're running the marathon with all your baggage. And what we have to do is create a great midlife edit that helps people to let go of that and allows them to have a school and a tool and an alumni system and a support network that says, yeah, you're going through navigating all kinds of midlife transitions from menopause to empty nester, to your parents passing away, to changing

your career, to getting divorced. But we have no rites of passage for these kinds of traditional things that happen in midlife. But we have rites of passage for people when they're going through puberty on some level. We have them at adolescence to adulthood, commencement ceremony, graduation. We have weddings. We have baby showers. We have funerals. But between baby shower and funeral, nada, nothing. So that's why I decided to build a campus to help people understand how do they make sense of a rather

baffling period that has a terrible branding because six, 55 years ago, midlife crisis is the term that we define for midlife and use all this pop psychology I've learned along the way to help people. I love it. I love every part of it. Like we've actually been influenced by many of the same teachers and we've had different paths obviously, but, um, the books that you reference and the, uh, the theories that sit underneath of them have been influential as well. So when you're speaking, I'm going, yeah, yeah, yeah, good. Oh. And then to know that you took your business acumen, you took your insights, you took, and I don't say this lightly, um, wisdom to be able to shape something for the next generation,

the now generation, meaning the baby boomers who are struggling to figure out like, who am I? Yeah. I was on this chase and new wealth is not big house, big car, big bank account. You know, I'm not saying there's anything wrong with those, but new wealth is a sense of vibrance, a sense of, um, flourishing. And how do we skill and arm folks with those practices that help with that? And that inner glow that people have and you have it, you know, is not from surgery. It's from the working from the inside out, like, Hey, I have what it takes to be able to adjust to the unknown, the unfolding unknown. And that knowing is very powerful. So it's like, Hey, I can actually just kind of flow. I can actually just be with it. And I love the challenge of figuring out like how I can be me in said environment.

And those folks that have invested in that tend to look like they are in love with life. Yeah. And you know, the glow that people talk about, oh, you're in a new marriage or a new relationship. The flow glow. The flow glow is a really powerful thought. And so I want to say thank you i can't wait to get down yeah to the academy yeah at some point let's talk well let's follow up and figure out yeah we have you'd be great to come and do a little mastery week like five days yeah it's

it sounds brilliant and so where can people find you where can they, where's the best place to get your books and learn about the Academy? So chipconley.com, one place, C-O-N-L-E-Y. The Academy website is modernelderacademy.org or.com. I'm on LinkedIn. I write a lot. I actually have a daily blog as well called Wisdom Well. That is literally a daily blog. You get a, it's like Seth Godin, who's my, was a classmate and great friend of mine from business school. It's like

him. It's a, it's a daily email people get. I was inspired by Seth's blog. Like it's super quick and pedantic and wonderful and open and like concrete and like nebulous sometimes, but the consistency, I don't know how to keep it up. I love it. I love it. I love it. I don't, of course I don't write it every day. I go and spend, I'll do, yeah, last weekend I did 11 in a weekend. And so that's basically, you know, more than a third of a month and, but I love it. And it's good. And people are really responding to it. So is there a sweet spot for number of words? Like you're 250, I think is the right number, but it doesn't, you know, I go above and below that depending upon it. But I, you know, sometimes he's got

like 10 words. Yeah. I'm going to check your, I, I, I try, you know, I try to have at least one out of every five, maybe 150 words or a hundred words or less. And yes, I've had some as little as 20 words. But yes, people go to Wisdom Well, which is on the modernelderacademy.com website. And on LinkedIn, I read a lot of LinkedIn. So almost all of my daily blogs go onto my LinkedIn exercise. I got to do this. Yeah. It's a good exercise. Yeah. You know, like, okay. So it's like a, it's like a wisdom snack. Yeah.

That's how I think of it. Like it's a micro dosing wisdom, you know, like how do you, how do you come up with something that is provocative, but prescriptive and small enough so people can actually take the snack in the morning. Somebody out of one of the enterprise companies has spent time with says, Mike, we need snackable insights from you. Yeah. It's a good little phrase, right?

It is. Snackable, you know? And the way people look at it now is mainly videos. It's like, you know, I wrote a blog post, which was funny. So Tim Ferriss is a friend and we did a show last year. And so it was like two minutes or two hours. Videos have to be two minutes, but somehow Tim, Tim Ferriss can do two hours. And it's like, it's all context, you know, it's all context. And so, you know, it's why generally prescriptive

rules fail a little bit because they don't give the ability to understand context. What did we miss? You know, I've got like 15 other questions, but I'm mindful of time here. Like, I want to know what you're searching for. And I didn't ask you that, but like, what did we miss that is really important to you? So let's talk about the word elder,

because the first time I was called the modern elder at Airbnb, I flipped the person and I said, fuck you. I'm not a modern elder. But I thought of it as modern elderly. And elderly is the last five to 10 years of your life. An elder is a different term, but one that has sort of lost favor in the last hundred years. It's a native term. It's an endearing term. It's a relative term. It only speaks to, it doesn't say what age you are. It says you are the older one around the

people you're surrounded by. I was 52 at Airbnb at that time. Average age was 26. So yes, I was an elder, but I was not the traditional elder. The traditional elder was regarded with reverence. I was the modern elder who was relevant, not reverent. And it's about learning how to be curious and wise. So yes, the word elder is problematic because we're trying to take back a word, but Malcolm X took back the word black. Black was not a positive word in the South in the 1950s. And he came back and said, black is beautiful. And black, you became a positive as has queer more recently, as has redneck. Redneck sort of own the word. You own the word, you became a positive, as has queer more recently, as has redneck. Redneck sort of own the word.

You own the word, you have power. And so I guess for me, because there's not a great word to describe a period of life when you actually are older than people around you, but you're not elderly at all. So it's modern elder for right now. That's what I'm working with. And we'll see. We'll see where it goes. More importantly, the idea of helping people to understand that they can be both curious and wise at the same time is amazing because it allows you to open up the

possibilities with curiosity and then distill down what's really essential with the wisdom. Brilliant. I hope that was good. Thank you. Yeah. Okay. So I'm all into bumper stickers. No. Yeah. Little bumper stickers. But the... There's depth to it. Your phraseology does not miss the depth of insight there. Okay. So I want to just say

thank you. And I want to thank Soren for putting us together. And I thought when you're going to talk about the retreat, you know, the spiritual, not the spiritual, the mindfulness retreats that you've been to some of his with Jon Kabat-Zinn. It's just the scheduling hasn't allowed it, but I do love that. It tends to be right at the end of the NFL season. It's January. It's really tricky for me. It's an amazing. We didn't get to talk about the Seahawks at all either. I know. I'm a huge, so it's so funny. I love, I'm like a big NFL fan.

So I know like gay man NFL, it doesn't make sense, but I am. And I have a lot of friends who are. So I just, you know, and I'm a big fan of the Seahawks. And I love that New York Times article about the variability. Like the fact that, like, it's a very unpredictable team in terms of scores and just like, you know, like, yeah, we've seen that. We've seen that over and over again. But Pete Carroll, I've never met Pete, but Michael has mentioned Pete in board meetings before.

And I just have a ton of respect for him. It was funny when Jim Harbaugh was at Stanford and Pete and like, you know, what's your deal? You know what I'm talking about? Oh, yeah. What's your deal? Post game. And I was like, you know, it's like those two are like so different from a psychological perspective. And I'm just, you know, happy to see how Pete has flourished.

And Harbaugh has not flourished quite as much. He's still doing fine. He's got a great job, but he's like, not like Pete. Yeah. You know, anytime you want to come up and kind of take a look at what we're trying to create. No, it's great. It's a model.

I mean, I really, I've, you know, a lot of people have asked me about it because they think of me as sort of a mindfulness dude in the corporate world. Right. And, you know, who's a practitioner. So I write books, but I'm not a consultant very much. I don't go out and help people to set that up. I don't have time to. But people say, you know, have you ever noticed this company or the Seattle Seahawks and what Pete Carroll talks about?

And he talks like self-actualization and stuff like that. It's like, yeah, yeah, I've noticed. And it seems to be working. It's been a great experiment, like a grand experiment in a rugged environment with alpha males. Like, can we actually strip down to the essence of the human experience and which is belonging, connecting, flourishing, and having the psychological skills and the cultural, um, environmental conditions to help people understand meaning and purpose and do their best work. You know, it's, we have a, again, an Aaron Taylor. I don't know if I mentioned this earlier. Aaron Taylor was on the, was on the

Packers. He won a super Bowl ring, linebacker. I think he's from Notre Dame. I don't remember where, but he's on our faculty. He's a former, very successful pro football player on our faculty, and he's great. He's awesome. And he's awesome partly because the identity challenge that football players go through, or any professional sports athlete,

when they are actually moving out of their their competing time is is awful because it started so early and and no and there's very little i mean we've actually talked with aaron about aaron what if we actually did like and and try to do this with the nfl with the Retired Players Association, do a program just for them privately to talk about how do you get rid of these identities and how do you actually shift into the next identity in a more conscious and intentional way. And Aaron loves it, but he said, like, I don't think NFL is going to do that. No, I think Aaron's right, is that I think it has to come. So you can have the outside entity, which is the badge, the NFL and the players association supporting that effort. However, if it's not in the water that

we're swimming in on a day-to-day basis and you've got the system, meaning the coach and the coaches and the cultural attributes of you're just a number and you only matter if you can do your job well, that anything that comes from the outside on a, you know, one hour basis, whatever, it's not, it's not big enough. You know what the big insight, I think a big insight is that the power of purpose and meaning, there's some research that will support it, right? And I'm sure you're familiar with some of that research, but just as a, as a case example is that every Sunday there's a purpose. Yeah.

And then, so every Wednesday, Thursday, Friday, there's a purpose that laps latches to that Sunday purpose. And when a person retires, they've had purpose, their whole, let's call it, you know, young adulthood for every Sunday, whether it's football or any other sport, fill in the blank. There's great purpose and there's meaning in the work they're doing, which is to support others and dah, dah, dah, dah. After that, what's the purpose? Yeah, no, this, this is, this is part of the reason why retirement tends to increase mortality rates. That's exactly right. And, and, you know, I mean, but, but, you know,

who's going to write the book about that for professional athletes, uh, to be able to help them to see, okay, how do, how do you create a transition that actually skirts that risk? Because that is a, that's an occupational health risk. Well, 87% at one point were broke, divorced, both post-retirement. Suicide is a real deal. Depression's a real deal. You know, floundering is, you know, like a tough, tough go at this. So yeah. Who's going to write the book? I don't know. And yeah, maybe you, maybe you and I do. How about it? You get number six on you. Yeah. All right, Chip. Thank you for sharing. All right. Thank you so much for diving into another episode of Finding Mastery with us. Our team loves creating this podcast and sharing these conversations with you. We really appreciate you being part of this community. And if you're

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