The Modern Elder: Chip Conley On Reframing Midlife, Cultivating True Wisdom & Finding Purpose In Life's Second Half

Chip Conley is a hospitality maverick, founder of Modern Elder Academy, and the entrepreneurial sage who helped transform Airbnb from a startup to a global phenomenon. This conversation explores midlife as a chrysalis rather than a crisis—a transformative journey from ego to soul. Chip illuminates the path from horizontal achievement to vertical growth, addressing life's longest yet least understood phase. We discuss his near-death experience, the nature of wisdom, and why friendship becomes essential to wellness as we age. In the process, Chip creates space for me to reflect honestly on my own lifelong pursuit of achievement. Chip is a treasure. This exchange is for anyone seeking to avail themselves of midlife's deeper possibilities. Enjoy! Note: Chip and I invite you to experience these insights in person in Los Angeles on June 5th for a special gathering with the MEA faculty. Register at meawisdom.com/richroll. Show notes + MORE Watch on YouTube Newsletter Sign-Up Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

• 0:00Rich Roll?

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• 1:05Chip Conley?

  We're living longer. How do I get older in a way that makes me feel good about myself? What if my best years are ahead of me?

• 1:15Rich Roll?

  In between being young and becoming very old, there's a stage of life that is not well enough understood and gets far less attention than it deserves. That stage is midlife, one we tend to only consider for the kinds of crises it tends to provoke, instead of seeing it for the opportunities it presents, and welcoming it for what it actually is, which, when done right, is an aspirational phase of life. Chip Conley is our expert in residence on all things middle essence, and today, the founder of the Modern Elder Academy, which is the world's first midlife wisdom school, is here for his third turn on the podcast to do what middle agers like myself are uniquely

• 1:55Rich Roll?

  suited to do best, which is to share his wisdom as a modern elder on what matters most when it comes to our middle years.

• 2:04Chip Conley?

  For so many people, they hit midlife and they sort of shut down. At least in adolescence, we're going through With a peer group, the kinds of things that we go through, the transitions of midlife in middle essence, we're going through often alone, but they're normal. So many of them are normal.

• 2:20Rich Roll?

  How exactly do we best pursue this multi-decade period of life so that we don't succumb to crises, regret and lament, and instead avail ourselves of the beautiful things that it presents so that we can live a deeper, more connected, fulfilling, meaningful and purpose driven life? I've got questions, Chip Scott answers, a manifesto for middle age, in fact, which is the title of his beautiful latest book. So please hit that subscribe button because Wisdom School is now officially in session.

• 2:54Chip Conley?

  10 years from now, what will you regret if you don't learn it or do it now? There are a lot of people who don't want to try something new after age 50. And then there's a growing number of people who realize that curiosity and openness to new experience are two of the most important variables for living a longer, healthier, happier life.

• 3:19Rich Roll?

  Chip, you're back. Delighted to have you here. So excited to dive deeper.

• 3:24Chip Conley?

  Sorry to interrupt your writing time.

• 3:26Rich Roll?

  It's fine. You're a welcome distraction to the torture of the page. So it's always a delight to spend time with you. We're going to dive deeper into middle essence. This is your third time on the podcast, but I do want to kind of set the stage and out of pure curiosity earlier today, I just wanted to find out what happens if you type midlife into Google. And of course, the word crisis is the first thing that comes up.

• 3:54Chip Conley?

  For sure.

• 3:55Rich Roll?

  So let's just start with like, why do we see it as a crisis still? And how can we see it differently, given the fact that this stage of life, which you have said goes from somewhere around 35 to 75 is the longest phase of life. And yet, despite all of your incredible activism and advocacy, still appears to be less well understood than it should be.

• 4:25Chip Conley?

  Well, let's recognize that there were three life stages that were that came into existence in the 20th century. Adolescence, as a word, didn't exist until 1904. Retirement was a thing starting in the 30s. And then in the 1960s, midlife got a lot of attention, partly because of coining the term midlife crisis. But also, midlife, when you have a people living till only 47 years old on average in 1900, midlife didn't exist. So we're still making sense of midlife. I'm trying to demystify it and elevate it and give it some operational chops. But the reality is Hollywood and Madison Avenue have had

• 5:05Chip Conley?

  a huge impact here. There's a sense that midlife, especially for men, was this thing that you hit it, your body was falling apart, you're becoming irrelevant, and so you go out and buy a red sports car like Leonard Burnham or whatever, Lester Burnham on American Beauty, Kevin Spacey, and you have an affair. And so I think that frame has stuck. And the reality is, very few people fit that frame. So that's why I like to say, it's not a crisis, it's a chrysalis, because it's a transformative time.

• 5:39Rich Roll?

  It is this extended period of transition. And whether, you know, you end up, you know, kind of reaching out for that red sports car, or, you know, having the affair, what have you, those are kind of outward manifestations of this internal struggle, which is this clutch to relevance and significance, like, look at me, I'm important. And as we get older, and our forms of intelligence start to shift, it's our resistance to this natural process that causes the suffering and the kind of less advisable behavior.

• 6:16Chip Conley?

  Brené Brown calls it the midlife unraveling. And unraveling has two, you know, meanings. Number one is, when you hear someone's unraveling, you think they're losing their mind. But what she said to me once, she said, Chip, have you ever looked at the word ravel in the dictionary? And I said, no. And she said, ravel means something so tightly wound, you can't get it undone, like a ball of string. And so in many ways, what's happening for people around 45 to 55 is they are unraveling their expectations and they're coming face to face with their disappointments. Because when you're 35, you still have hopes and

• 6:55Chip Conley?

  dreams that by 45 or 50, may seem like they're regrets. And so for a lot of people, what's happening between 45 and 55 is you're diminishing your expectations from life, such that by the time we get into our 50s, the U curve of happiness research shows that we get happier with each decade. And it's partly because we're expecting less from life and we're getting clearer on what matters most to us.

• 7:22Rich Roll?

  Hmm. In your experience, being somebody who's steeped in this and has been studying it and practicing it and teaching it as the founder of the world's first midlife wisdom school, what are, you know, some of the epiphanies that you've come across or learnings that are kind of most important for people to grasp and understand about this period of life?

• 7:48Chip Conley?

  Well, I think there's a gender component to it. And in past podcast episodes, we haven't talked about that as much. And I think that's become more and more apparent to me over time. For men, some of the issues that come up are virility, not virality, but virility, not being as virile as they used to be. And that's sometimes the physical body, but sometimes it's the sexual appetite. It's feeling, for the first time, if you're a straight white male, the ism of ageism. So for a lot of women, they've dealt with sexism. And if you're a LGBTQ person, you've dealt with homophobia. And if you're a person of color, you've dealt with some kind of racism. But if you're a straight white male,

• 8:30Chip Conley?

  And you're 52 years old, you can start feeling irrelevant and that doesn't feel good. It's the first time you have not been sort of the prizefighter in terms of sociology of what we've got in our society. So there's that. For women, it's perimenopause is a kick ass. I mean, it kicks your ass and it's hard for women. And on the other side of that, you may have some postmenopausal zest language that came from Margaret Mead. But when you're in the middle of menopause or perimenopause, it's not easy. For women, they're dealing with the odds against them when it comes to romantic life, the invisibility romantically,

• 9:10Chip Conley?

  70% of the people over the age of 50 who are single are women. So there's that. There's financial issues for women. There's caretaking issues for women. The sandwich generation taking care of older parents and taking care of kids at the same time. So I think one of the biggest things I've learned is, you know, you can't apply the midlife pair of glasses you wear to everybody the same way. At the same time, I'll say that across cultures, there's a lot of comparability, more so than 50 years ago. And what does that mean? It means that generally speaking, midlife is the time when you start to realize mortality is at the finish line. The grim reaper is holding the finish line tape. If

• 9:54Chip Conley?

  you have a perspective that death is a bad thing and you don't want to get old, then midlife will be a crisis. If instead you have what Becca Levy at Yale talks about, the pro-aging perspective as opposed to an anti-aging perspective, she says if you can actually shift your mindset from a negative to a positive in midlife, you gain seven and a half years of additional life. So in cultures like Latin America, Africa and Asia, you have historically had elders respected. But today, in those cultures, Google has replaced grandpa and grandma in terms of where kids go to learn things. And therefore, midlife crisis is an issue in those cultures as well.

• 10:36Rich Roll?

  Yeah, it's interesting from across cultures.

• 10:40Rich Roll?

  Cultural perspective, how people, you know, kind of interact with this phase of life, presuming that if you come from a spiritual or religious tradition that frames death, you know, very differently than the kind of Judeo-Christian

• 10:56Chip Conley?

  Yeah.

• 10:56Rich Roll?

  kind of perspective on it. In other words, one, you know, something that, you know, isn't something to be feared, but is transitional in and of itself, that that is going to inform your relationship with aging.

• 11:09Chip Conley?

  Oh, my God. You know, I 12 years ago, went to the Mahakumbh Mela, which just happened again in India. It was 100 million people 12 years ago.

• 11:18Rich Roll?

  Right. I've seen videos of it. It's unbelievable.

• 11:20Chip Conley?

  Hundreds of millions of people this year. What an experience. It's the Hindu rite of passage. People, you know, people walk hundreds of miles to this confluence of two actual rivers and then a third mystical river. They come together and every 12 years, they have this experience. Well, in the Hindu tradition, you know, the idea is like, okay, you're coming back. Reincarnation is part of the idea. So, so I was part of a stampede there. I mean, I wasn't purposely to stampeding. I was under, you know, four caked for people under, you know, I was basically run over by people and people died. And, you know, I saw dead people after the stampede.

• 12:03Chip Conley?

  But in the Hindu culture, there's a sense like, okay, they're coming back. And they were at the auspicious experience of Mahakumbh Mela. So they're going to come back in even better state. So it's a very different point of view than

• 12:17Rich Roll?

  That's extremely different.

• 12:18Chip Conley?

  A stampede in Grand Central Station.

• 12:21Rich Roll?

  Almost like it's aspirational to transition in the midst of that ceremony itself, right?

• 12:28Chip Conley?

  I mean, if you go to Varanasi, you know, in Varanasi, you see the bodies, you know, being laid into the, you know, the Ganges River and being burned and being burned on the river or before being put on the river. And so, so in many ways, or if you go to Bali, I mean, you know, my, one of my favorite places on earth, you know, just the idea of these cremation ceremonies and these celebrations. The idea that a rite of passage at death is just opening a window to the future, which means you'll be coming back.

• 13:04Rich Roll?

  It seems foundational that if you want to have a healthier relationship with, whether it's middle age or our elder years, that we have to first look at our relationship with death itself.

• 13:17Chip Conley?

  Oh, sure.

• 13:18Rich Roll?

  And interrogate that, right? Because doesn't everything else is downstream of this tremendous fear that we have?

• 13:23Chip Conley?

  I would recommend to everybody have an NDE.

• 13:26Rich Roll?

  Yeah, we talked about that last time. Although I don't know that I investigated that thoroughly enough. I mean, you had, basically, you died like nine times. You collapsed on stage, you had this infection.

• 13:38Chip Conley?

  I had an allergic reaction to an antibiotic. I was, you know, at Gavin Newsom's bachelor party, I broke my ankle playing baseball.

• 13:46Rich Roll?

  Your first mentee.

• 13:48Chip Conley?

  My first mentee. And long story short is I had this experience of going to the other side. And then more recently, I've had stage three cancer. So, you know, the Stoics talk about memento mori and the idea of having a remembrance of death as an organizational principle for how you live your life. There's a lot of value in it. There's a lot of value in writing your obituary and getting clear on what's important. We spend the first half of our life really building our resume, and we should be spending the second half of our life creating our eulogy. What do we want said?

• 14:30Chip Conley?

  One of my favorite movies of all time is It's a Wonderful Life, not because it's schmaltzy, but because, actually, it's a dark movie. Watch that movie again. It's a bit of a dark movie. But Clarence the Angel comes down to Jimmy Stewart, George Bailey, on the bridge before George is gonna throw himself off the bridge and commit suicide. He sees Clarence come down and says, "This is what Bedford Falls would look like, and it would be Potterville, based upon old man Potter who ran the town, if you hadn't lived." And I wish that we had a technology, and maybe we will in the future, a social technology that allows us to see the impact we've had on others.

• 15:14Chip Conley?

  And your impact, you know, Rich, I had people telling me way before I ever listened to one of your episodes, maybe six or seven years ago. About you. And so, you know, you're fortunate enough, and I'm fortunate enough, that we hear from people all the time about what impact we've had. But everybody deserves that. Everybody deserves to have their eulogy before they die.

• 15:38Rich Roll?

  This near-death experience also took place kind of at the bottom of your U curve of happiness, right? So you were in a bit of a existential crisis about your life that overlapped with that, that kind of added significance to that. And I'm sure is fundamental to like this whole chapter of life that you're in right now. Do you think that if you hadn't had that experience, that you would even be doing what you're doing right now? It's almost like the universe delivered this experience to you so that you could basically have your own chrysalis rebirth into this new chapter of life with some wisdom to

• 16:18Rich Roll?

  provide and a guiding principle to kind of give your life meaning and purpose?

• 16:24Chip Conley?

  Yeah, who knows? Yeah, it was a bit of a divine intervention on some level. I had five male friends lose, you know, take their lives during this time. One of them, whose name was Chip, you know, Chip Hankins, my insurance broker and one of my best friends. I was having some suicide ideation. I was, you know, at one point on my way to the Golden Gate Bridge, ready to jump. I called my best friend Vanda. And right as I talked to Vanda, as I pulled over to the side of the road, Aretha Franklin came on with the song Amazing Grace. And so I deeply believe that my life is meant to have some meaning. My favorite

• 17:07Chip Conley?

  book of all time is Man's Search for Meaning. And it's partly because what Viktor Frankl tried to get across in that book was the idea is that meaning is the fuel of life.

• 17:18Chip Conley?

  So sometimes I've come to realize over time that our past life lessons, our painful life lessons are often the raw material for our future wisdom. And it is that sense that when I, between age forty five and fifty, went through my bottom of the U curve of happiness, everything that could go wrong was going wrong. And then I had the NDE. It was a wake up call for me, which is pretty good because I was a hotelier. So the hotelier wake up call of saying, I need to have a different life. And the structures we have, sometimes our identities that define us, and sometimes our family and our friends and the infrastructure of our life

• 18:02Chip Conley?

  that says you have to be this person. You know what I'm talking about. I mean, I'm telling your story. There is a sense that you have to sometimes have something that breaks, that forces you to make the change. One of the things that I've learned over time is that there are three stages to any transition. There's the ending of something, there's the messy middle, the chrysalis, and then there's the beginning of something. And it's that anatomy of a transition of understanding which stage are you in? That's helpful for you to understand how do you cope with it. And so for me, when I had my NDE at forty seven, I was in the messy middle and I was stuck.

• 18:45Chip Conley?

  And so my midlife crisis was not buying a red Porsche or having an affair. My midlife crisis was being stuck in a chrysalis, feeling like I was going to be in this gooey, dark, solitary place for the rest of my life, which is part of the reason that suicide felt like it could be a possibility. So I ended up selling my company at the bottom of the market. If I'd waited three or four more years, I would have made a lot of money. And I made a moderate amount of money. But I got liberated. And it was in that liberation that I had time for my midlife atrium, the space to reflect upon how do I want to cultivate

• 19:29Chip Conley?

  the second half of my adult life? And, you know, that led to me being at Airbnb and being the modern elder there.

• 19:37Rich Roll?

  It isn't A midlife crisis, it's a midlife opportunity. Like, it is a transitionary phase. On some level, you can perceive it as, as, you know, being lucky if you're given this gift that forces you to look at yourself in the mirror. Because otherwise, we just pursue our lives, you know, kind of, you talk about like, the horizontal and the vertical. Like, we're pursuing it on this horizontal line that is really being driven by the ego. And fundamentally, is about like, what can we get? Like, we're trying to get things in our life. And then, at some point, we realize that

• 20:21Rich Roll?

  this pursuit of getting isn't actually delivering on the things that we, we need and want the most, which is meaning, purpose, happiness, satisfaction, all of these things. And we have to reconcile this. And, and that process is the crisis, right? Or it is the entering of the chrysalis. Yeah, this is the unraveling. And like, you've got to figure out another way to, you know, get these things, meaning, purpose, fulfillment, satisfaction, into your life. But you're in this moment where you have no idea how to do that. Because your whole life has been premised upon this other way that isn't proving to, you know, kind of deliver on the promise in the way that you thought it would.

• 21:05Chip Conley?

  Well, the way we show up in society as an adolescent or in early adulthood is loud, unmistakable, and full of social rituals that help us to understand who we are, the ego of who we are, the external identity of who we are. And midlife is a much more subtle, internal experience. It's not about the external identity, it's about the internal identity. And it is the process of actually shifting out of, creating the container, the, which is the ego and the way we face the world, to actually looking at what's inside the container. And for some people, that's extremely scary. Because with that will come

• 21:50Chip Conley?

  You know, skeletons in the closet from childhood. What that will come, disrobing from identities that aren't serving us anymore. At MEA, which we'll talk about, I'm sure, Modern Elder Academy. We call it the great midlife edit. Because the first half of our life, we're accumulating, and the second half of our life, we're editing. And the primary operating system for the first half of our life is our ego. But it's around midlife that Richard Rohr, one of our MEA faculty members, says that we move from the primary operating system being the ego to the soul. But nobody gave us operating instructions. And it's a very subtle process.

• 22:29Chip Conley?

  And sometimes it is external circumstances that force us on our knees to say, "Okay, I'm ready." You know, I mean, Arthur Brooks, who's on our faculty, been on your show a couple of times at least, speaks about the Strivers' Dilemma, the idea of the person who's constantly being successful. To my mind, when it's in midlife, if you've not been successful, you're disappointed, and you've got to unravel the expectations. If you've been successful, it's also a problem. Because you've gotten stuck in the straitjacket of these uniforms. You're wearing six different identities.

• 23:11Chip Conley?

  And I don't know about you, but if I'm at Burning Man, when I take off lots of uniforms or costumes all at once, it's very liberating. But a lot of people at age 50 or 55 don't realize how many uniforms they're wearing.

• 23:28Rich Roll?

  I would admit to succumbing to the Strivers' Dilemma. So here's where you're going to help me out. Well, first of all, your fellow midlife activist, Arthur Brooks, who's, obviously, he's been on the show a couple of times, he's a friend. His book, Strength to Strength, really gets at the heart of these ideas that you're talking about. I'm curious where his ideas might depart a little bit from yours, or where your perspectives kind of diverge. His idea, his whole thing is, the satisfaction that you're seeking is going to come from faith, family, and friends, basically. You need meaningful work, but what gets overlooked are those three F's primarily,

• 24:13Rich Roll?

  right? As we get... Older, those become much more important. And that gets into like crystallized intelligence and wisdom and all of that. But like, you know, what is your lens on like his work? And where might you see it a little bit differently?

• 24:29Chip Conley?

  I would add a fourth F, which I just came up with sitting here, and that'd be frolicking.

• 24:35Rich Roll?

  Okay.

• 24:36Chip Conley?

  Yeah, faith, family and friends are all essential. And just to recap his point of view, and he and I were teaching together at our Santa Fe campus in August.

• 24:50Chip Conley?

  He speaks to the idea that we move from fluid intelligence to crystallized intelligence. When we're young, our brain is fast and focused. And as we get older, we're not as good at things that require the linearity and the speed. But what we get better at is thinking in a crystallized systemic kind of way, which means connecting the dots. And so I totally agree with him on that. Where I might disagree, or at least add, is to say, there's a soberness to Arthur's work and to his point of view on midlife and beyond. There's definitely a sense of service. You know, I love Eric Erickson's point of view, which is at 50 and over, you know, the sentence you need to remember is, "I am what survives me."

• 25:36Chip Conley?

  So, you know, in my opinion, I'm in the business of serving these days. But I think what is missing there is the sense of frolicking. The idea of time affluence. The idea of being a beginner at things and being bad at it. And yes, you can be frolicking with friends and family, and maybe even in faith. But the idea that actually seeking awe and going out and with the time affluence you have as you get older, just having the best time of your life in terms of the things that might have been dreams earlier in your life. I reached out to my two sisters to like go and walk the Camino, which is not necessarily frolicking, and there's a faith element to that for sure.

• 26:22Chip Conley?

  But I haven't had time in my life to do that.

• 26:26Chip Conley?

  You know, I haven't had time in my life to learn to juggle, which is something I'm starting to learn. I haven't had time in my life to actually, you know, do a lot of things that I'm starting to learn to do. The key, I think, to having a great second half of your life. Is to actually shift out of the fixed mindset of I've got to prove myself and I've got to go and do things I do well to the growth mindset of I'm here to improve myself and I'm the definition of success is learning. And so the one of my favorite cocktail party questions I ask when I meet people for the first time is, so what in your life are you a beginner at these days? And a lot of people go running for the bar or for the bathroom because it's sort of

• 27:11Chip Conley?

  a weird question, but I but it's it's a pretty important one because if we only play games that we can win, our sandbox proverbial sandbox gets smaller and smaller and we get bored with life. And there are a lot of people we know who are our age, we're different ages, we're about a six year age difference, who are bored with life, but it's partly because they're not willing to become a beginner again.

• 27:38Rich Roll?

  I wonder if part of that also is due to just the calcification, you know, of the mind that sort of progresses as we get older, like we just become set in our ways, more resistant to things that are outside of our comfort zone. We like things the way we like them. We orient our lives around those things and it's easy to just not have to look at that stuff. And nobody wants to invest in the things they're weak at, right? And amidst that, we lose that relationship with play, though, like the fun and the frolic that you're talking about, like that just becomes a frivolous, you know, kind of triviality that, you know, isn't something that, you know, people of our age should be, you know, spending our time thinking about.

• 28:22Chip Conley?

  There's something called type two fun. And type two fun is when you're doing something that's hard and maybe embarrassing in the moment, but afterwards you laugh about it and and it actually felt good that and you're glad you did it. And so at MEA, we do that we like, we have people bake bread together, like, why do you do that? It's partly because there's collaboration, but also it's type two fun. You learn to surf, you learn to horseback ride, you learn improv, you learn karaoke. I mean, so the idea that we help people to be really bad at something and to do it in public with other people who are being bad at the same time.

• 29:03Chip Conley?

  And that's not the only reason people come, but it's it's a sort of subtle, underlying element because you're right.

• 29:11Chip Conley?

  There are a lot of people who don't want to try something new, you know, after age 50. And then there's a growing number of people who realize that curiosity and openness to new experience are two of the most important variables for living a longer, healthier, happier life. So Peter Drucker, famous management theorist, had a point of view, which was every two years, he would study a new topic that had nothing to do with being a management professor and an author, whether it was Japanese flower arranging or medieval war strategies. And he'd become one of the world's leading experts on it because he believed that curiosity and learning something new was like an elixir for his soul. So how do we do that?

• 29:53Chip Conley?

  How do we help people not calcify, but instead say, oh, I've got some time and I've got some, maybe, maybe if I'm lucky, I've got a little bit of money and I can go try some things and, and laugh at myself?

• 30:08Rich Roll?

  I've asked this question before, but I'm curious your perspective on it. Some people are naturally more curious than others. Do you think that curiosity, the more I think about curiosity, I really think this is foundational to, you know, well-being, longevity. Like if you can be curious about the world, about other people, about yourself, that is a sustainable source of fuel that is going to keep you engaged with life and, you know, kind of lead you in wonderful directions and new experiences, et cetera. But if you are somebody who is relatively incurious, is this a trait that can be taught and enhanced?

• 30:48Chip Conley?

  Yeah.

• 30:48Rich Roll?

  And how would you do that?

• 30:50Chip Conley?

  My friend of mine, Scott Shigiyoka, has a great book called Seek, all about curiosity. Curiosity is, is a skill. I mean, it's not an embedded way of who you are. I mean, we were all, as kids, curious. You know, the Harvard studies of showing that we ask 10 times more questions at age five than at age 15 suggests that we are born curious. And I believe that's true. And somehow, the curiosity gets bred out of us. And in the curiosity being bred out of us, we learn how to take tests, standardized tests. And then we learn to jump on the treadmill of a career path that doesn't give you time to be curious.

• 31:35Chip Conley?

  Curiosity is inefficient. You know, companies that want to be curious but don't create the space for it, let's be curious in this 30-minute meeting we're gonna have. That doesn't work so well. So curiosity requires a certain amount of being open to being wrong, open to asking bigger questions, giving the time and space to explore it. And then having a bit of a feverish passion for exploring and trying something new. You had the explorer, what was his name? Alex Hutchinson. Alex Hutchinson on the show not too long ago. Great episode. And about learning how to explore. And learning how to explore is something we do as kids.

• 32:17Chip Conley?

  Unfortunately, we have got kids to a place where they're not exploring as much, for safety reasons and for all kinds of reasons. But helping people to realize that, you know, there's an imposter syndrome. Jeff Hamouli, one of my co-founders, talks about the imposter syndrome needs to be replaced by the explorer syndrome, which means that you're asking questions as opposed to being self-critical. I like that. Learning how to seek out awe is an important piece of it. Dacher Keltner, who I think you should definitely have on your show, UC Berkeley professor, starred at the Greater Good Science Center, also on the MBA faculty, wrote a book a couple of years ago called "Awe."

• 32:57Chip Conley?

  Cultivating awe, it allows you to see yourself as something in a universe that's much bigger than yourself. Helps you to move and focus on the wonder of the world, not just the weight of the world. And so what he found, which was really interesting, he found the eight most common pathways to awe. Number three on the list was nature. You'd think that would be number one. But number one and number two are fascinating. Number one was moral beauty, and number two is collective effervescence. Moral beauty being witnessing compassion and kindness and courage. Courage and resilience and equanimity and feeling like if that person can do it, I can do it. Also, moral beauty is, you know, watching the birth of a baby. Collective effervescence is what we experience at Burning Man, which is the idea of ego separation

• 33:42Chip Conley?

  starting to actually dissolve and a sense of communal joy come in its place. You see a lot of that at Mahakumala as well. So the value in curiosity and and having a point of view that I am going to go out and do an awe walk right now means that you move out of the ghetto of the brain and the ego and into that childlike perspective of I am small in something that's much bigger than me. And that's really healthy for our egos, it's healthy for our humility, but it's absolutely healthy for bringing an inquisitive mind to the world.

• 34:27Rich Roll?

  Awe and wonder, you know, these are things that, you know, keep coming up on the podcast. They're abstractions, though. They're difficult for people to get their heads around. I like that that kind of way of of defining it, what it actually is, that could actually translate into a practice. Like, we all, oh, you know, you need to experience awe, go walk in the woods or whatever. But if your mindset, if you're not open and present to that because you're like obsessed with the guy you got to call back or whatever, you're never going to be able to have, make yourself available for that.

• 34:58Chip Conley?

  Yes, there are people who can't. But the thing you could do is you go walking with your dog regularly. What if you went walking at least one day a week for a longer walk with your dog, doing what I call spying on the divine, which means you go out and the question you ask, and you're not listening to Rich Roll's podcast when you're doing this, you're actually taking everything in by yourself with your dog, and you ask the question, nature, what are you here to teach me today? And just do it once a week. And instead of going for a 20 minute walk with the dog, go for a 40 minute walk, but go to a different location that you don't normally go to.

• 35:41Chip Conley?

  Because part of the reason we love to travel is because we have a different pair of eyes, you know, or glasses when we're seeing the place we're going to. If, you know, habits are awful because they get us stuck. I mean, the difference between a routine and a ritual, according to the African scholar Malidoma Somi, is in a ritual, you're willing to be altered. But we live our lives in a very routinized kind of way. And so the ritual of once a week, going into nature, spying on the divine and asking the question, "Nature, what do you have to teach me today?" And being open to that and then coming back and writing a few things. That is a practice you could actually develop in one's life and only have to do it once a week to get some benefit out of it.

• 36:25Rich Roll?

  So routine is the enemy of awe, the antidote of which is ritual.

• 36:30Chip Conley?

  Ritual. Ritual is, I love that, the quote, you know, the ritual, in a ritual, you're willing to be altered. In a routine, you're exactly the opposite. In a routine, and we live very routinized lives, in a routine, you want things to be the same. You know, so you're commuting in LA. So one of the things you could do is say, like, once a week, I go a different path and I drive a different path. It's going to be slower, you know, your routine is going to be more efficient. Again, curiosity is not efficient, but being willing to try something differently is good for your brain.

• 37:07Rich Roll?

  And the time affluence then becomes more important. It's sort of paramount to that, right? You have to carve out time to indulge these things.

• 37:15Chip Conley?

  I started my spying on divine thing during COVID. I was living in Baja, our MEA campus was empty for six months and bottom line was I had a lot of time. So Monday, Wednesday, Friday, from two till five, I went out and hung out with my dog, Jamie, spying on the divine. So you sometimes have to put it in your calendar. That's another thing. I mean, I try to keep my Sundays as a Sabbath. I am someone who is an extreme introvert. As a kid, maybe a little bit like you, that became a significant extrovert in my adolescence and especially in my adulthood. And as is true for three quarters, two thirds to three quarters of people over 50, I am moving back toward introversion. And so I'm a bit of

• 37:57Chip Conley?

  an ambivert. So my Sundays are my Sabbath where I, yes, I check email occasionally, I do, but I I'm out in nature and I'm usually by myself, partly because I need that. I know that's part of my, but I also need it from the curiosity perspective. And, you know, I like to write. And so, you know, I come back often from a two or three hour hike and I'm flowing with ideas. It's a great way to become the conduit, you know, I've spent most of my life being the can do it hero. But I want to be the conduit now, go from can do it to conduit. A few years ago, we had 3,500 employees in my company and Joie de Vivre, I gave every single one of those employees at our holiday party,

• 38:41Chip Conley?

  a copy of the book, The Little Engine That Could, because that was, that was the book that defined me. Like, okay, I think I can, I think I can, I think I can. You know, you and I have a lot in common.

• 38:52Rich Roll?

  Yeah, mine was the early bird gets the worm.

• 38:55Chip Conley?

  Yeah, it makes sense, which, which describes our swim, our swim, our swim.

• 38:59Rich Roll?

  Yeah.

• 39:00Chip Conley?

  You know,

• 39:00Rich Roll?

  That became the blueprint for my entire life.

• 39:03Chip Conley?

  Oh, my God. Yeah. So, so for me, I giving that away, I was like, I can do it. I, you know, I think I can, I think I can, I think I can. And I've come to realize that, you know, sometimes there's an archetype that defines us, or an identity that has been imprinted in our mind that we have to let go of, or at least dose it down. And for me, it's the hero. And it's like, I'm dosing down the hero. I don't have to be the can do it hero. I can be the conduit. Something comes through me. And part of my role, as I learned at Airbnb, when I went from being the CEO of my own company to being the guy behind the scenes, that, you know, the guide on the side as opposed to the sage on the stage, how can I?

• 39:42Chip Conley?

  Help support and serve and coach in a way that means that I don't have to do it all. I don't have to come in and save the day, which was a big ego stroking proposition.

• 39:54Rich Roll?

  The can do guy or the person who's, you know, getting up early to get the worm. You know, this is the archetype of the striver who ultimately faces the dilemma. Right?

• 40:05Chip Conley?

  Yeah.

• 40:07Rich Roll?

  You know, I'm definitely somebody for whom love has always been interpreted as transactional rather than unconditional.

• 40:15Chip Conley?

  Why is that?

• 40:16Rich Roll?

  And my deservedness to it is a function of, you know, what I can accomplish and achieve in the world. And that is so deeply imprinted, you know, in my soul as a consequence of a certain upbringing.

• 40:29Chip Conley?

  But so what's, but can we unpack that for a second?

• 40:32Rich Roll?

  Yeah, yeah, yeah.

• 40:32Chip Conley?

  I want to talk about.

• 40:33Rich Roll?

  This is the therapy session that I'm looking for.

• 40:34Chip Conley?

  That's right. Dave and Nancy, um, your parents, you know, I, I listened to your 2019 episode with your dad when his, when his George Marshall book was coming out and, you know, I can see he's a bit of a striver too. You know, he was corporate lawyer, antitrust lawyer. And, and by the way, how's your mom doing? Is she doing okay?

• 40:57Rich Roll?

  It's not a great situation. The dementia is, uh, is, is really, you know, kind of progressing rapidly.

• 41:04Chip Conley?

  Yeah. Um, this is another thing that we deal with in midlife for sure.

• 41:09Chip Conley?

  So, you know, you, you grew up in an environment where you're the only son and the oldest.

• 41:16Rich Roll?

  Mm hmm.

• 41:17Chip Conley?

  Same here. Uh, I happen to be chip, chip off the old block, Stephen Townsend, Connelly Jr. So the, I think part of it is how much of this was familial and how much was our own self-imposed. And, you know, I think over time we learn that.

• 41:35Chip Conley?

  You know, I'll never forget when my parents went out to dinner with me. We had a hotel in Huntington Beach that, you know, we were opening not too far from where I grew up in Long Beach called The Shorebreak. And my parents were doing an intervention on me without me knowing it. And so we're at dinner and they had come to the grand opening party and we were hanging out and they said to me something that I needed to hear, which was, Chip, we love you and for all of your successes, but we just love you for who you are. You don't have to keep being on that treadmill of success. And I, it was so unusual for me to hear that from them that I didn't know whether they

• 42:18Chip Conley?

  were my parents, because I'd gotten in my head, you know, through my actions that I am earning love. So it was really, I found it very awkward as someone, you know, my parents are not very, they're not naturally sort of personal growth kind of people or people who like to talk about the, you know, the deeper issues of life. And they were actually sort of doing this intervention to sort of like help me to get off of the treadmill. And it was frankly, maybe a year or two after that, that I had my NDE, which was what got me off the treadmill ultimately. But I would just say that I am still, I still throw myself back on the treadmill. I mean, MEA is the newest treadmill. Yeah.

• 43:00Chip Conley?

  The key is to say like, am I doing it differently than I've done it before? Because if we're repeating the past, we haven't learned the lesson and we haven't gained the wisdom. So we're supposed to metabolize our life experience, learn the lessons from it, and then change our life accordingly and share that wisdom with others. There's a beautiful quote from David Visco, "The purpose of life is to discover your gift." The work of life is to develop it and the meaning of life is to give it away. I would change gift to wisdom. The purpose of life is to discover your wisdom. The work of life is to develop it and the meaning of life is to give that wisdom away.

• 43:42Chip Conley?

  So I am doing it differently this time, but I'm still plagued by that occasional feeling like, Chip, go out and strive, strive, strive, even as someone who's teaching it. So, but at this point, I have let go of the parental piece of it. Thank God. And now I know it's, it's an inside job.

• 44:05Rich Roll?

  I would say I do that sometimes well, sometimes poorly, you know? That intervention is probably something I've been looking for my whole life and will never get, you know?

• 44:18Chip Conley?

  Don't say we'll never get. Dot, dot, dot, yes.

• 44:21Rich Roll?

  Trust me.

• 44:22Chip Conley?

  Have not gotten yet.

• 44:23Rich Roll?

  You know?

• 44:24Chip Conley?

  No, no, no. So wait, wait, wait, wait, wait.

• 44:26Rich Roll?

  Go ahead.

• 44:28Chip Conley?

  So you don't want to be calcified, do you?

• 44:30Rich Roll?

  Of course not.

• 44:32Chip Conley?

  Okay. So maybe you could be open with the dot, dot, dot, yet. You haven't gotten it yet. Or you've gotten it in small doses, you'd like to get it in bigger doses.

• 44:40Rich Roll?

  No, what I'm saying is it's, it's not that I'm not getting the idea and trying to embrace that idea and practice it as much as, but I'm taking responsibility for doing that for myself. And what I'm not doing is looking at like my parents to, you know, to say those things that I've always wanted them to say because they're not going to say it, you know, because they don't, that's not what they think or believe and making peace with that, like that's okay, right? While acknowledging that I have this way of being in the world that is very much rooted in my childhood experience that informs decisions I make as an adult. And many of those decisions are oriented around striving.

• 45:24Rich Roll?

  If I just get to that next thing or achieve that next level, then I'm gonna, you know, get the love and acceptance that I've been craving, you know, my entire life, right? And, and then instead doing that job for myself while also recognizing the ways in which I trip myself up along the way.

• 45:43Chip Conley?

  So there's, there's, Carol Dweck from Stanford popularized the idea of mindset.

• 45:49Chip Conley?

  And she says there's four steps towards shifting from a fixed to a growth mindset. The first one is you have to acknowledge and let go of the mindset you're ready to let go of, that isn't serving you anymore. So, you know, maybe the mindset is that I have to strive to earn love. And then the next step is to say like, okay, what triggers that mindset? Because just acknowledging it, letting go, at MEA, we do that at a fire and have people throw into the fire, what it is they're ready to let go of. But then you've got to look at the triggers, because just because you throw something away and let go of it in a sort of collective ritual, doesn't mean you don't have triggers that come up. For me, social comparison's a trigger.

• 46:32Chip Conley?

  So when it comes to, I love meditation, close my eyes, and you know, meditation's worked for me ever since I learned about it more than 40 years ago at Esalen. But yoga, on the other hand, has always been a struggle for me. Because I have my eyes open, and I lived in San Francisco a long time, and I was surrounded by people who were much better than me. And so, social comparison was my trigger. Once I saw that and realized that's my trigger, I started working with Teddy on our MEA staff to do one-on-one yoga. Because there was, other than with my dog Jamie, who does a mean downward dog, there was no social comparison. So the trigger's a really important piece. The third piece is to name it. So when you're in that state, Rich, and you're sort of saying,

• 47:17Chip Conley?

  this is how I'll always be, I will not be able to let go of being the striver, then you need to name it. When it comes to me, when it comes to yoga, I name it and I call it stiff upper chip. So like when I'm in a yoga class and I'm social comparison, and I'm laughing, and I'm very stiff in my upper body, I will try to laugh at it. Because laughing at something is the best way to learn. And it's the best way to move from fixed, where you're going to be self-critical about yourself, to a growth mindset, to actually being open to learning and open to seeing yourself in a new way. And believing that you can grow into a skill. And then the fourth piece is replacing it with something new that actually feels true to you.

• 47:59Chip Conley?

  So for me, the truth is not, I love yoga. The truth is, I love how I feel after a yoga class. So those four steps, letting go of, I hate yoga.

• 48:13Chip Conley?

  Seeing my trigger of social comparison and seeing if there's an alternative way to do it, having a naming of it so that I can say, oh, that is not Chip. That's just Chip when I'm in that state. This is not rich. It's just rich when he's in that state. And then going to the fourth step, which is, you know, replacing it with something new that can actually act as a magnet. So I know I feel great after a yoga class. I know the 10 minutes before it starts, I'm freaking out a little bit. And then 10 or 20 minutes into it, I'm like, fuck, what am I doing? There's so many other things I could be doing right now that I'd rather be doing, and I'd be doing better. But by the end of the class,

• 48:58Chip Conley?

  my body feels better. So it is that process, the kind of process of mindset management that shifts you, is so essential during midlife. Because in midlife, we have the opportunity, you know, if you're 54 years old, which is the average age of the person who comes to M E A, and you're going to live till 90, you have as many years of adulthood, 54 to 90, 36 years, as you do behind you of 18 to 54. So you're halfway through your adulthood at 54. You're 58. If you're going to live till 98. My dad and I went scuba diving in

• 49:33Chip Conley?

  Indonesia a few years ago. He was at the time 80. He's 87 now. And I was 58. And so I said to my dad before we went out scuba diving, my dad did not learn to scuba dive until he was 60. And then he did 2,500 dives between age 60 and 80. Wow. Partly because he would dive with sharks in the Long Beach Aquarium down here in Southern California twice a week. Long story short is, my dad said he was going to live till 98. And when I asked him, how long are you going to live, before we went out for scuba for the day. And he did the math for me. He said, Chip, if I live till 98 and I'm 80, I've just started the fourth quarter of my adulthood. And I did the math, and I

• 50:17Chip Conley?

  said, if I lived to 98, and I was 58 at the time, I was exactly halfway between 18 and 98. So one of the things we have to get used to is the idea that we have to have some longevity literacy to realize we're living longer. And so one of my favorite questions, and one I might ask you, and I'll answer it as well, is 10 years from now, What will you regret if you don't learn it or do it now? Because anticipated regret is a form of wisdom. So for me, I'll go first.

• 50:50Rich Roll?

  Yeah.

• 50:52Chip Conley?

  I asked this question when I first moved to Mexico, I don't know, eight or nine years ago. And this is how I went out from the mindset of I am too old to learn Spanish and I am too old to learn to surf. I, at age 57, started to learn how to surf, 56 or 57, and to learn Spanish. Now, I wasn't good at either, and I'm still not very good at either, but thinking about 10 years from now, at 66 instead of 56, how will I feel? Will I regret that I didn't learn Spanish 10 years earlier at 56? And, or I didn't learn to surf? So today, you know, I have sons who are 13 and 10, who are biological sons with a lesbian

• 51:34Chip Conley?

  couple, and Eli and Ethan, and I'm like, my, you know, what will I regret if I don't learn it or do it now is I will regret if I'm not hanging out with those boys at least, you know, and they live in Houston and I live in a variety of different places. I want to spend time with them a lot, you know, at least once a month or every other month, to just be with them because their teen years are really important. And I can't get that back. So that's the anticipated regret, which leads to the catalyst of like, okay, I've got to take this action. So what might you regret if you don't do it?

• 52:11Rich Roll?

  Yeah, I mean, it's a little different for me. I don't really think about learning new skills in that way. I have the benefit of having this career, this vocation, that nourishes my curiosity. So I have this privilege of being able to just say, I'm curious about this and I'm going to read this book and then I'm going to get the woman or the guy here and I'm going to talk to them. And I find that to be, you know, a way of kind of being in a growth mindset and always, you know, being open to new ideas and things, some of which I practice, most of which I don't, you know, it just goes into the soup. So I don't spend a lot of time thinking about like, oh, I need to learn how to juggle or I need to learn Japanese.

• 52:56Rich Roll?

  I would say, for me, they're more like ephemeral ideas, like...

• 53:02Rich Roll?

  I want to make sure that I'm having the most connected intimate relationship with my wife and my children that I can and that, you know, starts now. Like, you know, your future relationship with your kids is about like how you're managing that in the present moment, right? For sure. So like, doing those things to, you know, seed that future relationship into my older years. I mean, I would say that's the most important. I mean, there's things like travel and, and yes, I would like to, you know, have time affluence to focus on surfing and things like that. There are things that I want to do. But I think part of the problem

• 53:39Rich Roll?

  that, that feeds my strivers dilemma is that I started this thing that I love like much later in, like I've kind of found my thing late in life, right? You know, at 45, 46, you know, I, I started doing something that felt like the proper career path for me, that most people probably find in their late twenties or early thirties. Right. And there's positives and negatives about that. The positives are it keeps me fresh and young and I'm, I'm surrounded by people who are much younger than me, you know, and, and I delude myself into thinking I'm their age. The negatives of which are

• 54:21Rich Roll?

  that it's probably keeping me stuck in this relationship with my own ambition and achievement much longer than, than, than is healthy, right? Hmm. And I have awareness around that. So I think, you know, what would I regret? I would regret if I allowed, you know, my, my workaholism or obsession with my vocation to overshadow these things that are obviously long-term, much more important. But I am connected to this idea that I mean, you mentioned like, oh, you know, you put this thing out into the world and, you know, in terms of eulogy, like, that's meaningful for other people.

• 55:03Rich Roll?

  Yes, and like, I'm also aware that it's transient, like, I'm gonna, this thing will end one day and I'll be, you know, in my later years and eventually dead and everyone's gonna forget about this. It's like, it's not that big of a deal. So, learning how to like, hold on to it a little bit looser and not be so precious so that I can, you know, create the, the, the space, the time affluence to, you know, frolic and, you know, pay attention. It's like, hard to relax, right? Like, like, really prioritizing those things. And, and, and also, with friendship, which is a big thing, like, you know, I want to get into the friendship piece because there is a loneliness that happens at this

• 55:44Rich Roll?

  stage of life when you've lost touch with your friends and the phone feels heavy to pick up. And, and really getting into a habit of nourishing those friendships as this wellness practice that you talk about.

• 55:58Chip Conley?

  Yeah, well, I like to call it social wellness. And social wellness, you know, wellness starts with the letters W E, we, and illness starts with the letter I. And it doesn't mean that focusing on yourself is gonna make you ill. It does, is a reminder to me that wellness has a social component to it. And whether it's Phil Pizzo at Stanford, or Bob Waldinger at Harvard, or Dan Buettner, who's a faculty member at M E A, Blue Zones, they all show the same thing, which is the number one correlated variable with living a longer, healthier, happier life, is how invested are we in our social relationships in midlife and beyond. This is a big issue for men. So, we were talking about earlier about midlife

• 56:42Chip Conley?

  crisis for men versus women. Women are less lonely in midlife than men are. And it's partly because women have kept their social relationships and that muscle in their twenties, thirties and forties. Women actually are much better jugglers. And men actually often have let that go. And so, they all of a sudden have some time affluence and they don't have anybody to share it with. Or they're in their fifties and it's not a surprise that, you know, men tend to actually commit suicide or to die by suicide much more than women, partly because they don't express what's going on inside. It's a powder keg. And so for a lot of men, their friendship muscle is atrophied.

• 57:25Chip Conley?

  And it's around midlife that they start to realize that. But then they don't want to talk about like, I'm lonely or, you know, I don't have friends. And because that they feel like a loser and, and they don't know how to be vulnerable. And they don't want to necessarily talk to their spouse about it because they feel embarrassed. And they, they end up, you know, we get a lot of men at MEA who come and it's like, wow, I have been underwater with no air for decades. And I've needed the sustenance of, you know, collective effervescence and being connected to other people. Jeff Emery, one of, again, one of our co-founders at MEA, talks about friendship as a practice.

• 58:08Chip Conley?

  So if friendship were a practice, how might you come at it differently? If you had some intentionality around it? You know, I give a lot of speeches and sometimes for a longer speech, I'll be on stage and I'll say, okay, take out your phone, which is the last thing a speaker usually is going to say to an audience, but take out your phone and I want you to spend the next two or three minutes crafting a simple text to somebody you have not been in touch with for a while, who's important to you and meaningful to you. And you can say to them just how much they mean to you. You can say, hey, I would like to do a Zoom call with you, or I'd like to catch up and go for a walk with you. And I want you to do that right now. And it's really interesting afterwards.

• 58:52Chip Conley?

  I give all the speeches and I have, you know, slides and all that. The thing I hear over and over again is like, thank you. Thank you for giving me the space to do that. And it's sort of weird. It's like, you could have done that on your own. But the fact that everybody-

• 59:04Rich Roll?

  But it's very practical and simple and achievable.

• 59:06Chip Conley?

  Everybody's doing it at the same time. Everybody's doing it and that we all have now dedicated three minutes to actually making a connection. And my connection with Alan Mouchwar, who I'm going to call out here, who is somebody, my best friend in high school. We both went to Stanford, you and I both went to Stanford, you know, a few years apart. We, you had Skip Kenny as your coach in swimming. I had Dante DeDeVante as my coach in water polo. Alan and I went to play water polo at Stanford. He was really good.

• 59:34Rich Roll?

  He was an 88 Olympian, I think, right?

• 59:36Chip Conley?

  He went to the Olympics. He would have gone in 80, but we didn't go to, where is it? Russia, I guess it was.

• 59:42Rich Roll?

  Uh, yeah.

• 59:42Chip Conley?

  Yeah, it was Moscow. And 84, he was in medical school because he became a doctor. Alan and I were like, we're buddies. And then we went sort of separate ways. I became a business person. He became a doctor. And, you know, he got married and was straight. I was gay and, and we lived different lives. And last summer, I decided I was going to invite 16 of my friends from high school to the MEA campus in Santa Fe to go through the program together as a way of reconnecting all of us at that point about age 63 or 64. And I reached out to Alan and I said, you know what? I really want you back in my life. Now, it took some vulnerability to say that,

• 1:00:25Chip Conley?

  but he came with his wife, Janine, and I'm like, and my partner, Orin, is Israeli and she's Jewish and like, oh my God. And so then they came and hung out with us in Baja and we're, we're good friends again. But it required me to be open to being vulnerable and putting that out there. And the other thing I'll just say is that for a lot of people I know that come to MEA, we have 7,000 graduates from 60 countries. They come and they say, you know what? We had, we had third vault conversations here. I'll talk about what third vault is in a minute. And I can't have that with my friends or my family members. And, you know, what I think is true a lot of the time is that you've not outgrown your friends. You've outgrown the conversations you're having with your friends.

• 1:01:10Chip Conley?

  So the question is, how do you open that up? And one of the things I learned at MEA was this guy, Aaron Taylor. He was a NFL, um, Super Bowl winner, uh, he won the Super Bowl twice with the Green Bay Packers. Um, and Aaron was a, you know, big husky lineman, went to Notre Dame, offensive lineman, first round draft pick. And, and then he spun out of control, as a lot of people do, a lot of athletes do, when he got, had an injury at 28 and all of a sudden his, he was, he went from being a VIP to a PIP, a previously important person, because he'd spent his whole life since, you know, adolescence, being a big time football player.

• 1:01:55Chip Conley?

  And he had drugs and alcohol issues. And long story short, he found His way to sobriety. And he ultimately said, there are three ways we communicate in life. The first vault in our communications are the facts of our life, often in our brain. That's who, how we talk to each other at a cocktail party when we're meeting people for the first time. The second vault is in our heart and it's the stories. And stories can be both liberating, but also incarcerating. Because often we get stuck in our stories and our friends and family members remind us that we do. And then the third vault is when you're speaking with others from the essence of who you are,

• 1:02:35Chip Conley?

  that gut, that soul, that unfiltered, unplanned way of communicating, which, you know, you do on this podcast, conversation matters. And so that is what people, that's what people are starving for, is not small talk, it's big talk. And it's the idea of having deep conversations with each other. If you want to have long-term friends, have deep conversations. And so, you know, Arthur Aaron has his 36 questions that will help you fall in love. You break that out with another couple and have, you know, once a month, have a dinner with another couple where you're going over three of his 36 questions.

• 1:03:18Chip Conley?

  Come to MEA to a workshop with your spouse and another couple and have that kind of connection as a result of it. Too many of our relationships today are both partisan, but also surface level. And we deserve, as we get older, to peel back the onion to see what's there.

• 1:03:50Rich Roll?

  So let's like paint an example. Imagine, you know, everybody has their Alan Mushwar, right? You know, like that friend they haven't talked to for a long time that they miss and they'd like to have back in their life. Their history with that person dates back perhaps decades. And maybe despite this rich

• 1:04:10Rich Roll?

  Deep friendship was one because of age was relatively surface level. You want to reach out to that person, you understand the three vault, three vaults of communication. You know, but to go right to vault three, like out of the gate, like, how do you, how do you begin to cultivate that with somebody who, you know, maybe isn't like super interested in going to the MEA campus to do it, right? Like a practical version of like picking up the phone and, you know,

• 1:04:40Chip Conley?

  Well, start, start with,

• 1:04:41Rich Roll?

  Rekindling.

• 1:04:42Chip Conley?

  I mean, you know, Dale Carnegie famously helped people to know that the most important thing people want to hear is their name and, and questions about themselves. So be curious about the other person. Not necessarily inquisitive questions that are going to be off putting or, you know, too sensitive. Just start with the basics. Start with the first vault. The first vault is, you know, is people are very comfortable and conversant in talking about the facts of their life. And then you can get into the stories of, of someone's life, but to try to go to vault three immediately in normal life, not in a workshop kind of format. Yeah, that doesn't make a lot of sense unless it's a friend who says,

• 1:05:22Chip Conley?

  you know, I want to be intimate with you and I really want to have a conversation that's going to go deep. So yeah, so I would just say you start with the simple stuff. But, but there's nothing wrong with at least putting it out there that, hey, I'm reaching out to you. I haven't talked with you in 20 years. Partly because I've been thinking about you occasionally and I was just curious how you're doing. And, you know, it'd be great to at least do a quick catch up. When you do mentorship in the world, and I've done a lot of mentorship in the world, you don't start with the M word mentorship, just like you don't start with the M word marriage when you're dating. You start with, hey, let's just do a catch up. Because if you say, oh, you know, I'd like to have a deeper friendship with you again.

• 1:06:07Chip Conley?

  That may feel really weird to someone who hasn't had 20 years. Now, in case of Alan, I just said, you know, we're going to be having this thing this summer and I wanted to like catch up with him. I reached out to him on Facebook Messenger and that's how it happened. But it, what happened over time is the, the, the onion got peeled back.

• 1:06:26Rich Roll?

  Yeah, maybe don't start with, hey, you know, we're in middle age. If we want to have more kind of like connection and meaning in our lives, friendship is important. It's important to longevity.

• 1:06:40Chip Conley?

  Well, you can say that again, that might work with someone who's very, very much in their head. And, and let's also recognize, you know, we were talking about this at M A with, with Derek, our CEO the other day, and we're, you know, doing some longevity programming. And Derek was like, how do we get, you know, how do we get more men to come to M A? And it's like, longevity? Like, like, men are obsessed with, not all men, but a lot of men are obsessed with longevity. If you look at the podcasters who are obsessed with it, they're almost all men. And, and so longevity is a way that you, if you're a man, trying to open the door to another man to have the conversation, it's like, hey, this is something I heard, you know, maybe we can try it out. I would say I'd be cautious about saying that because sort of it sounds sort of geeky and, and weird.

• 1:07:23Chip Conley?

  But it is true. At the end of the day, you know, our friendships are what sustain us. They're not nice to have, they're need to have. They are not the wallpaper in the living room of our life. They're the furniture we sit in, and they got to be comfy.

• 1:07:38Rich Roll?

  Yeah. This question that you, that you asked around regret, if you don't do something now, or, or, or learn it now, and, and this idea of anticipative regret being a form of wisdom. This is the first in five questions that you have that everybody who is in or approaching middle essence should be asking themselves. And the second one, I kind of want to go through them. The second one is, how might you curate your life if you knew you'd never retire?

• 1:08:08Chip Conley?

  Do you think you'll retire? And what does retirement mean to you?

• 1:08:11Rich Roll?

  I don't even know what that means. Like, that word doesn't feel relevant. Like, of course, there will be a moment where this thing that we're doing right now, I won't be doing it anymore. But I don't know that it's going to be an on off switch. It'll be, you know, a slow transition into something else. But I don't foresee or imagine myself in a situation in which I'm not doing anything, you know, and just like, sitting on a dock fishing. Like, I don't aspire to that. I aspire to time affluence and being able to kind of enjoy life,

• 1:08:51Rich Roll?

  you know, without being kind of captured by too many obligations or responsibilities professionally. But I, as long as I'm capable of,

• 1:09:02Rich Roll?

  Being productive and contributing, I'm sure that I will find ways to do that.

• 1:09:08Chip Conley?

  So, exactly. And what you just said, Rich, is what so many people who are, you know, Gen Xers and, you know, younger boomers are saying, which is the idea that my parents' generation of how they did it may not be how I do it. And there's a lot of reasons for that. And, you know, back in the day when retirement communities started to be built and populated, the average age of people going into them was 65. Today, it's 82.

• 1:09:34Rich Roll?

  That's so crazy. Like, how old, you're six?

• 1:09:37Chip Conley?

  I'm 64.

• 1:09:38Rich Roll?

  You're 64, so next year?

• 1:09:40Chip Conley?

  I go into a retirement community.

• 1:09:42Rich Roll?

  And in six years, I would be doing that? Like, is unimaginable.

• 1:09:45Chip Conley?

  Okay, so that's the past. But let's also recognize that it was an on-off switch. You worked for the same employer. You know, the average number of jobs a person had back in 1960 in the course of their career was three. Today, it's 13. And so, the bottom line is, people would actually do backbreaking labor. They were not knowledge workers. And when they got to the place where they could get a pension or social security, they would retire. And they would retire and have the leisure life. And so, we sort of created this age apartheid. Young people learn, middle-aged people earn, and retired people adjourn.

• 1:10:27Chip Conley?

  And they sort of go off to their, you know, age apartheid retirement community. And today, you know, the people who are retiring are often not manual labor people. I mean, the people, you could understand why someone wanted to retire at 60 when they've been doing backbreaking labor. But today, it's knowledge workers who are retiring, and their brain is still very vivid and full of ideas. And so, the idea that you're going to actually go retire and, and put your brain on hold doesn't sound very appealing to people. So, this question, which is, if you knew that you were going to live and never retire, and you also knew you were going to live till your 80s or 90s, so you may be doing some

• 1:11:09Chip Conley?

  form of work, and, and again, people are doing this portfolio life and titrating down their work, maybe they're working 25 hours a week instead of 65 hours a week. Or 45 hours a week. And so if you knew that, you might curate your life differently. You might say, I'm going to take a midlife atrium, which, you know, in retrospect, I did. But I did because I was so burned out and because I had no idea what I was going to do next. So the difference between, what is the midlife atrium? This is a term that came from Mary Catherine Bateson. And she said that, you know, most people think that their extra longevity is adding an additional bedroom to the backyard of life, as if you're just old longer. And instead, what she said is, no, you're, the ideal way of thinking about life is around

• 1:11:54Chip Conley?

  the middle of your life or around the middle of your adult life, which for a lot of us is around 50 to 55 or 45 to 55. We find time to create an atrium, because what's an atrium? An atrium is a space to actually reflect and have the light and air to imagine how you want to curate the second half of your life. A lot of people could use that. We, as a society, could use people saying, oh, I'm having my 50 year gap, my, my gap year at 50, just like you have your gap year at, after high school or after college. Maybe 50 deserves a gap year. And we can create a social construct that helps people to say, ah, it gives me the time and the space.

• 1:12:38Chip Conley?

  And maybe it's not a year, maybe it's just a month. I mean, literally a sabbatical and actually taking a month off is remarkable. And we talked about the Camino, you could go walk the full Camino in a month. There's a lot of things you can do and it really rewires the brain. So at the end of the day, I guess what I'm suggesting here is that this idea of earn, um, learn, earn, adjourn should be shifted. And I think, you know, younger people, millennials and Gen Z are teaching this, this, they are learning to say like, okay, I'm taking a break. You're taking a few months off. Whereas back in our era, the idea of having your resume have a gap in it was a problem. Like there's something wrong with you.

• 1:13:23Rich Roll?

  Yeah. And if you're not going to retire, what are the things that you would imagine enjoying in retirement and reverse engineering your life to make space for them?

• 1:13:34Chip Conley?

  That's right. I mean, how many people do I hear who come to MEA or, you know, and, or just in life? And they say, during the time of life, when I really wish I'd had time, I had no time. I had time poverty. I was taking care of my parents. I was taking care of my kids. I was having to pay the bills. I was stressed out. I had no time for any reflection. And so how might we re-curate our lives? How might we be age fluid? A term that I really love and have coined with the intention of saying, at times in our life, we should be 75 and other times we should be 15. And we should have the age fluidity of being both of those things. You should be all the ages you've ever been,

• 1:14:17Chip Conley?

  at any age. And so I think learning how to break out of the game of life mentality. Remember the game of life, that board game where it had one path through life? And you got your little plastic car and you got an extra token in there if you got married? And if you got your promotion and you bought your first home? And it was a, it was a form of American propaganda that meant you had to stay on that path.

• 1:14:44Rich Roll?

  Within the lines.

• 1:14:44Chip Conley?

  That's right.

• 1:14:46Rich Roll?

  It's kind of a nasty piece of business, that is, isn't it?

• 1:14:49Chip Conley?

  Well, thankfully, I think younger people are learning.

• 1:14:52Rich Roll?

  It is true.

• 1:14:53Chip Conley?

  They're learning it partly because like they're recognizing that the American dream that we grew up with, which is that maybe we're going to have a better parent, you know, adulthood and, and life than our parents, especially financially, is less true today than it used to be.

• 1:15:09Rich Roll?

  It's less available and also it's less appealing. You know, because they, they've seen, you know, their elders in various states of unhappiness. You know, having spent their lives pursuing it and are young enough to dream something different for themselves. And, and I do, I do see a greater kind of commitment to the things that do matter, which are connection, experience.

• 1:15:39Rich Roll?

  And trying to orient their career trajectories around things that are meaningful as opposed to kind of self-aggrandizing.

• 1:15:47Chip Conley?

  And diversity as well. I think there's a premise that you want to break out of hanging out with people who are just like you. And I think that we live in a culture in the United States where that is more true today than it used to be. And you know, this is not getting up on my DEI, you know, soapbox, but I'm just saying that we have, we live in a more diverse culture. Just even the math on it, the demographics of our culture is different than it used to be. And therefore, people saying like, okay, well, maybe I'm going to go and spend, I'm not going to live in the United States when I get older. I'm, you know, I'm going to live overseas. I'm going to be an expat. And not because I've

• 1:16:29Chip Conley?

  been taking a gap year, but because I'm going to choose to raise my kids in Spain.

• 1:16:33Rich Roll?

  Yeah. I think the bigger problem is, is around the lack of opportunity and kind of upward mobility that used to be, you know, much more accessible.

• 1:16:47Chip Conley?

  Buying that home.

• 1:16:47Rich Roll?

  And what, what that is doing to the younger generation, adding in or layering on top of that, like the ills of social media that are driving, you know, kind of the loneliness epidemic and all kinds of, you know, terrible outcomes right now. Like, this is a problem. This is a, this is, you know, its own unraveling that needs unraveling, and that's a different podcast. But in terms of this stage of life, this middle essence, we talked a little bit about friendship, but this gets to the third question, which is how are you investing in your social wellness? So beyond what we've already talked about with respect to our connection with friends, what else is packed into that question?

• 1:17:30Chip Conley?

  Yeah, I think the thing I would really emphasize here is something I learned in Sunday School, make new friends and keep the old one is silver and the other is gold.

• 1:17:42Chip Conley?

  Your friendships that you've had from a long time ago can evolve. And the ones that don't, maybe you have to move on from them. But I want to just say, talk about intergenerational friendships for a moment here. Because it's not just about necessarily being friends with the people who are your same age. When we, when we do research on this at M E A, we find that about 80%. When we ask people to say, who are the five people other than family members who know you best? And most intimately? And if you were struggling, you'd want to have a conversation with them. Who are those five? And you write down the name and write down their age. And then we, after they've done that, we ask them, what number of these five are at least 10 years older than you, or at least 10 years younger than you?

• 1:18:27Chip Conley?

  And again, these are not family members. And 80% are usually within a 10-year band of you. So 80% of them are roughly your same age. We need to break out of that. We need to figure out, how do we create more intergenerational collaboration and friendships? Because we have so much to learn from each other. I mean, one of my greatest experiences at Airbnb, being a boomer amongst the millennials, was how much I could learn from the younger people. Yes, I was supposed to be the mentor. I was the modern elder, you know, the person that they called as curious as I was wise. But what I loved was how much I could learn from the people who are younger than me, including a different perspective.

• 1:19:08Chip Conley?

  So when you're thinking about social wellness, or friendship as a practice, consider the idea that a, you know, you can, you're gonna have to break out of your age apartheid in order to actually open up to friendships that are with people who are older and younger than you. And it's a good thing.

• 1:19:28Rich Roll?

  You talk about these intergenerational friendship dinners, right?

• 1:19:32Chip Conley?

  The Generations at Dinner, yeah. We started something called GenerationsAtDinner.com, and you can, you'll find it. And we serve up like a Jeffersonian dinner. Here's some questions you could ask. And we've had seven generations in Tel Aviv, in Sydney, in Denver, in Toronto. When you have seven generations at the table, you have five-year-olds, and you have people who are 90 years old. The ideal is, you know, three or four generations, because when you have people that disparate in age, you know, it's sort of, it does drag down the conversation a little bit. But to have a conversation around purpose or about the world's problems and how are we going to solve these problems, or love and relationships across the generations

• 1:20:15Chip Conley?

  is quite beautiful. And quite frankly, it's quite historical. It's how we used to do things, because we often lived intergenerationally in families.

• 1:20:23Rich Roll?

  Part of this is about the transition from being kind of a knowledge worker or somebody who has that fluid intelligence into the crystallized intelligence version of yourself, which is about being a wisdom worker, right? Like, I want to talk about wisdom for a minute. So first of all, like, how do you define, like, what is your definition of wisdom?

• 1:20:47Chip Conley?

  It's metabolized experience that you share. So being smart or savvy is not a social good. Someone can be smart or savvy, and we know people like this, and they hoard it, their smart and savviness, for their own good. But wisdom, for thousands of years, has been a social good. It means you share it. So it's understanding how do you make sense of your life lessons as the raw material for your future wisdom, but wisdom you can share with others as well. So it's different than knowledge. We are awash in knowledge, especially in the era of AI. You know, all of the world's knowledge is at our fingertips.

• 1:21:30Chip Conley?

  But wisdom is different than knowledge. Knowledge is local. Someone could be knowledgeable about a particular topic, but you wouldn't want to ask them about, you know, some relationship advice. But when someone's wise, it's across domains. So knowledge is local, wisdom is global. And I mean that sort of figuratively. It means that when someone's wise, it's valuable across domains. And so wisdom is a way of looking at the world. It's a sense of how the world works, based upon the School of Hard Knocks.

• 1:22:01Rich Roll?

  So crystallized intelligence is really this capacity that we develop to leverage all of this knowledge that we have, mixed in with all of our experiences, to create or, you know, kind of synthesize wisdom that it then becomes, if we want to pursue a life of meaning and fulfillment, it becomes our responsibility to, like, share for the benefit of others.

• 1:22:27Chip Conley?

  Yeah, I think wisdom's making a comeback.

• 1:22:29Rich Roll?

  I think it is, too. But the interesting thing about wisdom is that The younger generations, you know, that were kind of oriented around like sharing it with for their benefit are most resistant to it, right? You know what I mean? It's like for centuries, for the, you know, the history of humankind, right? You know, our elders are the receptacles of wisdom, right? The oracles. But younger generations seem pretty insistent upon having to learn these lessons themselves, right? So that they can then, you know, develop their own synthesized, crystallized intelligence to in turn share with a younger generation that's resistant to hearing it. Like we, like, we have to figure these things out for ourselves.

• 1:23:14Chip Conley?

  Yeah.

• 1:23:14Rich Roll?

  You know? So what is that gap between like, you know, the wisdom, the truth of the wisdom and like actually being open to receiving it and putting it into practice?

• 1:23:29Chip Conley?

  Well, there's so much here. Let's start with some just data points that, and that is that in the next two years, according to the US Department of Labor, the majority of Americans will have a younger boss. We've never seen this before. So we are living in a culture in which, generally speaking, power is moving to younger people. And workers are staying in the workplace longer. So that's number one. Number two is 75% of millennials say they would like to have a mentor and only 1% actually have one. So that's interesting. And Deloitte has shown that when a mentor, when you have a mentor within your organization in a company and you're a millennial, you are more than twice as likely to stay at least five years.

• 1:24:12Chip Conley?

  So there's something to this idea of like, how do we develop a mutual mentorship? What you are describing is the historical perspective on mentorship, which is it goes from old to young. I learned at Airbnb, it goes in the opposite direction. The physics, you know, the waterfall can move up, up the stream too, in that I could learn things from someone younger than me. The problem with a lot of, you know, older people trying to actually share their wisdom is number one, it's hard to do with, with your kids. Let's just start with that. That's, that kids and mentorship don't usually go together. But number two is OK Boomer as a, as a meme came about because a woman said, like, there's

• 1:24:53Chip Conley?

  a guy who worked with her, who actually, she put a hand in his face and said, OK Boomer, because the guy was telling her how the world works. So thinking that your war stories are wisdom is probably ill-advised. So you don't lead with the war stories. And you definitely don't lead with saying, here's how the world works. What you lead with is curiosity and openness to like what it is the other person wants to learn. And I wrote a whole book about this called Wisdom at Work: The Making of a Modern Elder, based upon that premise. How can you start by evolving your own self so that you're curious?

• 1:25:31Chip Conley?

  Because younger people will lean in if you're curious and passionately engaged, because they'll notice your energy, not your wrinkles. But if you're coming across as authority, you will come across as a parent. And people will disengage. So, long story short is, one of the things that I really strongly believe is that we all, at any age, can get wise. When I was 28 years old and I had been running my boutique hotel company for two years, I was an idiot. I didn't know what the hell I was doing. And one day, I went home and took a journal off the bookshelf, and I wrote on the cover of it my wisdom book. And I started a practice that I've been doing for 36 years now,

• 1:26:14Chip Conley?

  which is every weekend, I spend 20 to 30 minutes making a list, in a bullet point format, of what I learned that week. Personally, professionally, psychologically, relationally, spiritually. And I say, what did I learn? And then, what am I going to do with that learning? How will it serve me in the future? And I do that with my leadership teams in my companies. They're like, once a quarter, we sit down at Jwadaviv and Airbnb and at MEA, and it's like, okay, what did you learn this quarter? And how's it going to serve you? And it's an awkward thing if you have a dysfunctional team. But at the end of the day, for me, you can accelerate your wisdom at any age.

• 1:26:58Chip Conley?

  Based upon the idea of learning what the lesson was. And a 70 year old is not necessarily wiser than a 30 year old. You could have two, a 70 year old and a 30 year old in a kitchen. And the 70 year old has a lot of more raw material, that is, life lessons. But if they don't know how to cook, all of that, those, you know, raw material for the, for the recipe, don't mean anything. If you're a 30 year old and you have a lot less ingredients, but you know what to do with them, you can cook a great meal. So, there are a lot of 70 year olds who have a lot of raw material, but they've never made sense of the lessons from that.

• 1:27:39Rich Roll?

  So what would the process be? I mean, you mentioned the journaling, but like, the process of helping that person make sense of it?

• 1:27:47Chip Conley?

  One of my favorite questions at M E A is this idea of like, we all have wisdom. And the question is, if you were to take your wisdom and put it on a bumper sticker, a bumper sticker of wisdom, that feels like it's your wisdom, your wisdom fingerprints on it, not Oscar Wilde, who said, be yourself, everyone else is taken, which is a great line. But your wisdom based upon a life lesson. What is the origin story of that, that bumper sticker? So from, you know, my bumper sticker, I, you know, I did not prepare for this, so I'm going to just off the cuff just say, what's a piece of wisdom I might say? If a younger person came to me and said, I'm going to have lunch with you in a week,

• 1:28:30Chip Conley?

  I'd like you to come to lunch with a piece of wisdom and the origin story behind it. One of the ones I would come up with is, you can't satisfy everybody. When I, the origin story there was Jeannie Obagi, who I loved, one of my high school friends. She came up to me and said to me, everybody in the high school likes you, and therefore I don't like you. And I said, well, why don't you like me? And she says, it's because everybody else likes you. And as a people pleaser, I was like, well, what the hell? You've just messed with my, like, my-

• 1:29:06Rich Roll?

  It's amazing that you still remember that.

• 1:29:08Chip Conley?

  I do. I remember it from age 16. And Jeannie, I'm sorry that I've mentioned you here, but I remember it. And that, so, what that helped me with, and as a reminder all the time, is that sometimes you can't satisfy someone. You know, you can do your best, but I can't force genie to like me. So we have life lessons. I mean, many of mine are business lessons and I could go through a bunch of them right now, but I'm not going to. Those lessons are jewels. They're really, they're value. There's value in them. But if you hit a younger person over the head with them, and let me tell you how the world

• 1:29:49Chip Conley?

  works, you know, when I was with Brian Chesky, so Brian Chesky is the CEO and co-founder of Airbnb and I was his mentor for seven and a half years I was in the company, four years full-time, three and a half years part-time. When Brian was running a meeting in the first few months, I would sometimes interrupt him. Now, I reported to Brian. Brian was 21 years younger than me. I reported to Brian, but I was also his mentor. Weird situation. And so I didn't think he was running a meeting well. And so I sort of like commandeered the meeting. And I realized at that moment, like, wow, I need to intern publicly and mentor privately. The mentor privately meant, you know, I needed, if I had feedback for Brian about how he was running the meeting, I should say that privately, not publicly.

• 1:30:34Chip Conley?

  Like, you know, his parent giving him feedback in front of everybody else in the room. And intern publicly means be curious, be open to being not the one who knows everything in the room, be the most curious one in the room, not the smartest one in the room. Because quite frankly, in tech companies, it's often a bunch of people who are the smartest people in the room trying to one-up each other. So, you know, that, again, that's another lesson I've had that's, you know, another bumper sticker.

• 1:31:00Rich Roll?

  Well, this is the, the fifth in your series of questions, three pieces of advice to your younger self and the origin story for each that illuminates them.

• 1:31:10Chip Conley?

  Yeah.

• 1:31:10Rich Roll?

  Right? And this is a practice we can all do, and these are questions we should ask, we should ask ourselves. Like, what are our bumper stickers?

• 1:31:17Chip Conley?

  That's our exercise we could do with ourselves. But you could also do it, you know, at MEA, we do it with, you know, someone else. And then we, you know, come back together as a, as a whole workshop cohort and we start mining the wisdom in the group and, and there's a lot of wisdom. But what's beautiful is the, the origin story behind the wisdom, because that's, that's what's really interesting, is to understand where did that wisdom come from? You know, when I ask someone, you know, do you make better decisions today than you did 10 years ago? 90% of people say yes. But that, why is that? It's because what you learned, it's the painful life lessons of the last 10 years that made you wiser. But you don't think of, we think of wisdom as being this abstract thing.

• 1:31:59Chip Conley?

  It's like, you know, the thing that philosophers and, you know, but no, we all have wisdom. You know, we learn it along the way. And the why is, I think, wisdom making a comeback right now is because knowledge is just proliferating, it is a commodity. And so, helping people to create wisdom management practices in their life, which is really what MEA is all about, helps us to realize, no one, I can learn wisdom from someone else, someone can share some wisdom, but teaching wisdom is something you do yourself. You actually, and you have to go through a process that helps you to learn that. And a great coach, or a great therapist, or a spouse, can be very helpful here, because often we're not objective to see, seeing what we're learning.

• 1:32:42Chip Conley?

  What we see as common sense, is to some, to someone else, like, wow, that's amazing.

• 1:32:51Rich Roll?

  It is interesting. And reflecting on, on the, the, you know, advice I would give to younger people, like, all of my instincts around that are like, pieces of advice, based upon, not something that I did well and benefited from, but like, things I didn't do well, or wish I had, right? Like, the things that stick out are like, you know, for example, like, like, you know, invest in experience, you know, it's because I didn't do that. You know, I didn't do enough of that, and it's only, you know, in retrospect, with age and wisdom and experience, that I can look back and say, oh, you know, if I could do it again, I would do that.

• 1:33:35Rich Roll?

  And I would like younger people to know that that would be something, you know, worthy for them to consider.

• 1:33:42Chip Conley?

  Yeah, I think the value in this exercise, and mining that archaeological dig inside of yourself, is it helps you to realize how much you have learned in the course of a lifetime.

• 1:33:59Chip Conley?

  And in back to the question about meaning, meaning being the fuel of life. Viktor Frankl was in a concentration camp and he saw that people who passed away were often the people who had lost hope and meaning, not the ones who were the most physically infirmed. So this idea of meaning, meaning comes from the idea of feeling like you're learning something along the way. And, and so it's, it's a beautiful practice also for people to just feel like, okay, my life has meant something. I've got something and I also have something to, to give away. So, I mean, for me, in terms of my life, it's like, wow, I'm now at a stage in my life where I'm, I'm constantly still learning. You and I are going to be together, I think.

• 1:34:43Rich Roll?

  That's right.

• 1:34:44Chip Conley?

  We're doing, we're doing a, an LA based, an event on June 5th around wisdom and learning and about curiosity and midlife. It's an all day thing with a bunch of M E A faculty and open to anybody and it's on the M E A website with a backslash of Rich Roll. But you and I are going to spend the, the latter part of the day doing a fireside chat in person, talking about all of these things. And specifically, I, you know, it'll be a conversation. I want, I really want to like plum the depths.

• 1:35:15Rich Roll?

  Yeah.

• 1:35:16Chip Conley?

  Of Rich a little bit. I know you like being, you know, I liked hearing Roll on last week. It was good to hear that again, but I, you know, I, I like it when we can understand Rich, the human beyond the, the amazing conversationalist.

• 1:35:30Rich Roll?

  Well, I'm looking forward to it.

• 1:35:32Chip Conley?

  Yeah.

• 1:35:33Rich Roll?

  Yeah, I, I kinda want to just go in like blank, like, all right.

• 1:35:36Chip Conley?

  We are.

• 1:35:37Rich Roll?

  We're gonna just hit me and see what happens.

• 1:35:40Chip Conley?

  Well, that's more fun.

• 1:35:41Rich Roll?

  Yeah.

• 1:35:42Chip Conley?

  Yeah, you know, I, I know you prepare a lot for these interviews and that must take a lot of time and, but like just having a conversation, you know, one that meanders and goes wherever it needs to go, you know, who knows? That's, I'm, I'm excited about being able to do that. In fact, that's how we met. And now that I think about it, we met in Miami, a couple, two or three years ago, maybe three years ago, at a Y P O event because you were the M C. And you're emceeing. And so they asked me, well, would you like to do a presentation? Or would you like to have Rich Roll interview you on stage? And we'd never met before. And I said, yeah, I'll throw the dice and do the Rich Roll thing. And so, yeah, and we did no preparation for that. I think we just got up there and-

• 1:36:27Rich Roll?

  No, we pretty much winged it. There's a funny backstory to that event, which is, I'll tell it quickly. Because it illustrates, you know, kind of putting yourself in new situations. Like, nobody had ever asked me to emcee an event before. And so when that came up-

• 1:36:42Chip Conley?

  So you freaked out?

• 1:36:42Rich Roll?

  No, I was like, oh, that sounds fun. You know, that'll be cool. Like, the pressure's off me. I don't have to, like, get up and do a keynote. I just have to be the person who's, you know, kind of like handling the in-betweens and making sure the audience is kind of, you know, queued in as to what's happening.

• 1:36:59Chip Conley?

  Yeah.

• 1:37:00Rich Roll?

  And then I arrived in Miami. And when I really looked at, like, what this job was gonna entail, I realized I was completely out of my depth. And I started to have a panic attack. And I was like, oh, my God, like, I don't even know, like, there's so much here. And I had, like, a day to get ready. And I should have been preparing for weeks leading up to this. But I called my buddy Asher Gunsberg, who is an Australian television host extraordinaire. Like, he does all the big TV shows, you know, The Bachelor and, you know, all the- So like, this is what- He's like the Ryan Seacrest of Australia. So luckily, I had, like, the perfect guy. And on the phone, he just walked me-

• 1:37:42Rich Roll?

  He was so patient, walked me through his wisdom and experience to get me in a place where I could handle this, right?

• 1:37:50Chip Conley?

  And be a beginner again. And be a beginner again.

• 1:37:53Rich Roll?

  I thought, well, like, I talk to people. Like, how hard could this be? Not really appreciating that this was an entirely brand-new skill set that I didn't have at all.

• 1:38:01Chip Conley?

  Well, having to do one after another, after another, after another. And frankly, the people who you bring on here, I mean, it's deep two hours.

• 1:38:11Chip Conley?

  But when you have that environment, you know, you're going to get some clunkers up there and like, and then trying to bridge between people.

• 1:38:17Rich Roll?

  Yeah, like being the connective tissue, keeping the audience engaged, entertaining them, letting letting them know what's coming up, helping them understand what just happened and why and all of it. It's like a whole thing. Like I have so much more appreciation for for people who do that for a living than I did before. You mentioned the June 5 event. So I wanted to ask this question, which is, in your capacity, running MEA, having all of these teachers come through and all of these students, which are, let's face it, are sort of a self-selected group of people. Like, these are people who are already prone to, you know, all of the things that you're trying to teach. Like, they signed up for it and they paid for it, right?

• 1:39:02Chip Conley?

  Or their spouse was.

• 1:39:03Rich Roll?

  Yeah, all right. Yeah, so maybe you have those reluctant, you know, individuals coming, you know, under duress. But but I'm curious around what you've discovered or learned about people who are able to, you know, learn these things and gracefully make this transition successfully versus people who are unable or less successful in doing it. Are there any kind of common traits or characteristics that you can identify like, oh, this person's going to get it? This person isn't?

• 1:39:35Chip Conley?

  Yeah, there's sometimes there are flight risks. Like, you know, it's a it's a five day workshop. It's in Santa Fe or in Baja, and we do online courses as well. But often the person who I think is a flight risk, meaning that they're going to they're going to leave after 24 hours, it almost it's happened maybe three times out of 7,000. It's somebody who's not prepared to explore their life. They're they're really sort of in a place where they showed up and they, for one reason or another, are just maybe a deer in the headlights. But we have people who are like hardcore, you know, corporate lawyers, litigators. We had a litigator a few years ago, a couple of years ago, came to a cultivating

• 1:40:18Chip Conley?

  purpose workshop, and she came at 60 years old, prepared to work for her, all of her 60s. She would, she said she'd graduate at 70, retire at 70, and, but she hated being a litigator, and she wanted to do something different. She thought she had, she could be a, maybe a litigation consultant or something, so she wouldn't have to be in the courtroom. But by the end of the week, she realized that she wanted to be a pastry chef. That's what she'd always wanted to be. So, and she ended up going to pastry chef school. Now she's an entrepreneur as a baker. Often, people get very regimented in their thinking,

• 1:40:57Chip Conley?

  that I am this, and therefore, I have to focus on an adjacency that's close to it. And, you know, when, the moment you take the blinders off, the moment you start to have more options. And so, those who flourish, and, you know, we have 58 regional chapters around the world, so it's about a bit of a movement, are people who are open to saying, I'm gonna be willing to put on a different pair of glasses, and see myself a little bit differently, and be open to the tools I'm learning here, that I can take home with me, and to live a better life. And so, we have firemen, we have elementary school teachers, because we have financial aid, you know, we have, it's not just tech CEOs or investment

• 1:41:42Chip Conley?

  bankers. And that's part of the beauty of it, to be in a workshop with, you know, 20, 25 people, who are a very different collection of people. You learn a lot from them.

• 1:41:52Rich Roll?

  So it's really, the impediments here are being closed down emotionally, such that any kind of deep self-interrogation is interpreted as a threat, right? And then, kind of ancillary to that, like, how, how hard are you holding on to your identity?

• 1:42:12Chip Conley?

  Yeah.

• 1:42:12Rich Roll?

  And can you release that? Like, until you can summon the courage to kind of investigate yourself, and, and let go, like, kind of release your grip on who you think you are, like, those are the entry points towards making progress.

• 1:42:25Chip Conley?

  Yeah. The main reason people come, is they're going through some kind of transition in their life. And whether the transition is menopause, or it's changing careers, or retiring, or empty nest, or a cancer diagnosis, or parents passing away, you know, getting divorced. When people are in transition, they are often more open to exploring new ways of doing things, similar to me in my NDE. And that's why, you know, if anybody is curious about this, you can go to the MEA website at the bottom footer, MEA website, meawisdom.com, and you'll see the anatomy of the transition that helps people to understand, you know,

• 1:43:07Chip Conley?

  how do you transition in whatever your transition is? Because that's really the core of our program. It's TQ, Transitional Intelligence, applied to people in midlife.

• 1:43:22Rich Roll?

  So TQ versus EQ and IQ.

• 1:43:26Chip Conley?

  That's right.

• 1:43:27Rich Roll?

  Like transitional intelligence.

• 1:43:28Chip Conley?

  Yes, we have copyrighted the term Transitional Intelligence.

• 1:43:35Rich Roll?

  Ever the businessman.

• 1:43:36Chip Conley?

  Yeah, that doesn't mean we don't let other people use it. But yeah, you know, we live in an era in which knowing how to navigate transitions and mastering transitions is a modern skill set. It's really one that we all need. And when we go through adolescence, we're going through all kinds of transitions with a social infrastructure. You're doing it with people exactly the same age, and you're going through your first kiss, your, you know, your first SAT test, your first job with people who are similarly aged. When we're going through the kind of transitions we go through in midlife or adolescence, sometimes we're not talking about them. We have no social infrastructure to support them. And sometimes we're doing it at different ages, especially if we've had kids at different

• 1:44:19Chip Conley?

  ages, if we have kids. So long story short is, you know, having a social infrastructure, which is what MEA provides, and a toolbox for knowing how to navigate transitions is the primary reason people come and the primary reason they come over and over again. So I mean, and we have a, you know, Maria Shiro was on the show recently and she's a friend. And, you know, the Hoffman Institute with the Hoffman Process is sort of a good dovetail for this. Hoffman is what you do to sort out your past and sort of family of origin stuff. And M E A is what you do when you actually say like, okay, what's next?

• 1:44:56Rich Roll?

  Moving forward.

• 1:44:57Chip Conley?

  Yeah.

• 1:44:57Rich Roll?

  Yeah. So paint the picture of the ultimate middle essence champion. Like, what is this archetype? Like, who is this person? What is their mindset? And what are the behaviors that they're exhibiting? Like, the ultimate, like, you know, gold medal winning champion of this transitionary phase of life?

• 1:45:20Chip Conley?

  They're someone going through maybe two or three transitions at once. They are, one of the transitions might be a newfound spirituality that has been dormant since they were a kid. So they're curious, but they're also somebody who's been a corporate, in the corporate world, as a strategist and using their left brain to an extreme. And they're a little burned out. They're feeling a little stuck. They don't really know. They know what they want to change their career. They just don't know to what. They are separated from their spouse of 25 years. And the kids, the two kids have left home. So they're feeling

• 1:46:04Chip Conley?

  a bit alone. So that's the, that is a, that's a profile. Now, that profile has a lot in it. Not everybody has all of that in it. And that's a person, whether that's a man or a woman, that is coming with an openness to saying, I want to understand how I'm going to go through these transitions. What's the T, how do I build my T Q? What's my purpose in life? You know, and I think that purpose is often summed up by something that excites you, or agitates you, or something that feels you're curious about, or something that actually feels lost from childhood, maybe neglected. And then what wisdom do I have inside of me? And how, how, how do I get older in a way that makes me feel good about myself?

• 1:46:50Chip Conley?

  What if my best years are ahead of me? And so that person comes, they have their five day experience. They are a part of a cohort of people who stay in touch from all over the world, because we've had people from 60 countries come to either of our campuses. And long story short is they stay in touch with their cohort. Some of these cohorts have stayed in touch for seven years with weekly or monthly Zoom calls. And they go back to wherever they live. Let's say this person lives in Chicago and they're part of a regional chapter in Chicago of other M E A alums. It's an ecosystem and it's a bit of a movement. And I've written this book recently called The Midlife Manifesto that just really captures the sort of the, I don't know, it's like it's Reader's Digest version.

• 1:47:34Chip Conley?

  It's a very short book, short, you know, it's a short read. They capture some of the highlights of some of the key elements of the program.

• 1:47:44Rich Roll?

  It's beautifully rendered and illustrated though.

• 1:47:47Chip Conley?

  Thank you.

• 1:47:47Rich Roll?

  You did a great job. And I know you worked with Seth Godin on it.

• 1:47:50Chip Conley?

  Well, Seth and Seth and I wrote a book together long ago.

• 1:47:54Rich Roll?

  You were in business, we talked about that before.

• 1:47:56Chip Conley?

  Yeah, we're in business school together.

• 1:47:58Rich Roll?

  Yeah.

• 1:47:58Chip Conley?

  Seth actually talked about, he has a definition in the book of manifesto. So what's a midlife manifesto? It's a call to arms. It's a call to action as opposed to just a deliberation of a bunch of words. And so that's what this is because for so many people, they hit midlife and they sort of shut down. And instead I, I, I look at it as, you know, as, as this newfound midlife activist as an opportunity for people to see it as that metamorphosis, the chrysalis that they're about to break out of so that they can be the butterfly, you know, putting their wisdom out in the world.

• 1:48:37Rich Roll?

  The spirituality piece is something that I suspect kind of creeps up on people, right? Like, it's inevitable when you reach a certain stage of life and you start asking yourself the deeper questions that perhaps unconsciously you're making room for, you know, the ineffable in a way that maybe you haven't prior, right? And it is this stage, just to kind of, you know, really highlight this part of it, where you have to go from, you know, ego to soul. And that horizontal line where you're pursuing the ego has to suddenly shoot vertically upwards, you know, towards something greater and more powerful

• 1:49:22Rich Roll?

  than yourself. And for a lot of people, that's a difficult leap, right? I think it's an opportunity that the world, the universe, whatever you want to call it, like, presents you at this stage of life where perhaps there's a greater openness to these ideas than there wasn't prior. And with that, like, this, you know, experience of being nourished in a new and different way that maybe you haven't been your entire life.

• 1:49:50Chip Conley?

  Yeah, it's a muscle, just like friendship's a muscle, you know, the kinatrophies, spirituality is a muscle. And it's a muscle about sort of the inquiry of what is bigger than you. And I believe the soul rests inside of you, the spirit rests outside of you, and it's seeing yourself as part of a bigger constellation. And for a lot of people, that's, you know, death or mortality or the recognition of it is what takes them there. Sometimes, for some people, it's the life quake, to use a Bruce Feiler term, the author, the life quake of having a mashup of multiple transitions happening at once in midlife that takes them there.

• 1:50:34Chip Conley?

  You know, as I said earlier with Richard Rohr, the idea of the operating system shifting, and all of a sudden, you get curious about things that you didn't have time to be curious about before. Trust that. I mean, I think it's part of the reason why introversion, people moving in their 50s into a more introverted state. This has been going on for centuries. I mean, millennia. The Hindu, the Hindu had this thing about the forest dweller. And it's the later part of your life, you go back to the forest from which you came. And you're, you know, from a sort of figurative metaphorical perspective, your body is supposed

• 1:51:16Chip Conley?

  to become the forest. You're supposed to disintegrate into the forest. And that's your job is to, you know, I'm actually, as we talked earlier, I'm having a conversation with a very well-known CEO who left his job in not the best way, not in a way that he's been successful his whole life, a striver. And he's a little bit lost right now because of the fact that like, his identity has been this. But I've, I know this man. I've known him for 20 years. And I know that he's got a curiosity and inquiry about spirituality that's quite deep in him. And so, you know, we're gonna spend some time this afternoon and tomorrow, he's one of those people, and I wouldn't say this to everybody, who I just

• 1:51:58Chip Conley?

  know this is the time of life in which he's supposed to deepen that inquiry, whether that's going to divinity school, or volunteering at his church, or reading the great books. You know, I, for some of us, that's what our later life is supposed to be.

• 1:52:15Rich Roll?

  Yeah. I think it would be good to share a little insight, or encouragement, or wisdom for the person who's listening to this or watching this, who is in the middle of this transitionary phase, and, you know, doesn't, doesn't have the skills or the, the TQ, right? What is the message that you want that person to hear about how to engage with?

• 1:52:40Chip Conley?

  Number one, you're not alone. Number one, when we're teenagers going through adolescence, we can feel alone. I mean adolescence is very difficult. I mean, I loved your role on conversation about the Netflix series. Adolescence is tough today, but at least in adolescence, we're going through it with a peer group. The kinds of things that we go through, the transitions of midlife and adolescence, we're going through often alone, but they're normal. So many of them are normal. So number one is you're not the aberration, you're the normality. Number two is there are people who've gone through what you're going through now and they've learned something. They've built some wisdom around this.

• 1:53:24Chip Conley?

  How do you find a place with friends or family members or a workshop where you can share wisdom with others? Because you probably have some wisdom inside of you as well. There are lots of free resources, podcasts, there's lots of books, there's lots of, on the MEA website, at the bottom, there's a footer, there's all kinds of free resources. Read, but also don't do this alone, whether it's a coach, a friend, a therapist, or somebody in your life who can be there with you. I wish my five male friends who ultimately took their lives had felt the comfort to say they were going through a difficult time. So don't do this alone.

• 1:54:08Chip Conley?

  You will find that the gift you're giving is not just being able to move through this fog that you're in and realize that you're not alone, but you're going to actually feel like, and feel the sense that you're giving a gift to someone else who's able to help you through that fog.

• 1:54:27Rich Roll?

  And one of the many gifts that you are giving is this new book, The Midlife Manifesto. So if you are struggling or trying to make sense of this period of your life, I would strongly encourage you to pick it up. And to Chip's point, you can learn everything about what he's doing at meawisdom.com. And if you want to attend the June 5 event in Los Angeles, it's meawisdom.com/richroll.

• 1:54:53Chip Conley?

  Exactly.

• 1:54:53Rich Roll?

  And we're both going to be there and who knows what's going to happen.

• 1:54:55Chip Conley?

  Yeah.

• 1:54:56Rich Roll?

  It's going to be good. And you've got some great teachers this year, right?

• 1:55:00Chip Conley?

  Oh, we've got Liz Gilbert, Michael Franti, Arthur Brooks, Anne Lamott.

• 1:55:06Rich Roll?

  She's great.

• 1:55:06Chip Conley?

  Yeah, just a, you know, a bunch of Michael Mead, the mythologist. He's a very interesting guy.

• 1:55:11Rich Roll?

  I don't know. I don't know him.

• 1:55:13Chip Conley?

  Oh, he's, yeah, he's, he has a podcast called Living Myth. He's probably the most famous mythologist, Joseph Campbell, on the planet today. Yeah, just, you know, we specialize in, oh, Krista Tippett. Krista Tippett from On Being is coming at the end of June. I love her. So I'm really excited to be teaching with her in that, in that workshop in Santa Fe.

• 1:55:34Rich Roll?

  That's cool. So you too can attend one of these, you know, events and you can learn more at meawisdom.com. So thanks, buddy. I love you.

• 1:55:43Chip Conley?

  Love you too.

• 1:55:44Rich Roll?

  You're a gift. You know, the work you're doing is, is super important and you're speaking to an incredible need out there, you know, that millions and millions of people all over the world are benefiting from. So thank you for your service.

• 1:55:57Chip Conley?

  My best to Dave, Nancy and Molly.

• 1:56:00Rich Roll?

  Yeah, good. Thanks, buddy. To be continued.

• 1:56:03Chip Conley?

  Yes.

• 1:56:04Rich Roll?

  All right. Cheers.

• 1:56:05Chip Conley?

  All right.

• 1:56:19Rich Roll?

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

• 1:57:04Rich Roll?

  This show just wouldn't be possible without the help of our amazing sponsors who keep this podcast running wild and free. To check out all their amazing offers, head to richroll.com/sponsors. And finally, for podcast updates, special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo. The video edition of the podcast was created by Blake Curtis and Morgan McRae with assistance from our creative director, Dan Drake. Content management by Shana Savoy. Copywriting by Ben Pryor.

• 1:57:44Rich Roll?

  And of course, our theme music was created, all the way back in 2012, by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Plants. Namaste.