How to Love Midlife: 12 Ways Life Gets Better with Age | Chip Conley

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Episode Transcript:

Chip Conley: [00:00:00] Instead of just learning how to grow old, we’re learning how to grow whole. When you hang out with someone who has presence and is 75, 85, 95 years old, what you notice about that person is that they are alchemically whole. They are not compartmentalized in being present. They feel like they have somehow taken all of these constituent parts of who they are and who they’ve been, and how they’ve lived their life, and woven them into this potent mix of this human. You get to that stage, there’s a radiant being that you have become.

Jonathan Fields: [00:00:38] So imagine a world where midlife isn’t some crisis to endure, but an invitation, even a sacred initiation into your deepest wisdom and most vibrant potential and genuine happiness and peace of mind. For many, that vision feels a bit like a mirage. Oh sure. Nice in theory, but completely out of reach and out of touch with the real-world experience of that season of life. But what if it wasn’t? What if, no matter how our bodies and our health and our relationships and our work and environment change, we still had the capacity and the tools to make what has now become the longest season of our lives the best. That’s where I’m headed today with my guest and friend Chip Conley, who’s a bit of a midlife visionary and best-selling author of Learning to Love Midlife 12 Reasons Why Life Gets Better As We Age. So as a successful entrepreneur who founded the joie de vivre boutique hotel brand and more recently, the Modern Elders Academy with campuses in Baja and Santa Fe. Chip experienced his own radical midlife metamorphosis and this journey, it sparked a deeper calling to explore and share insights about the profound transitions of midlife and so many of the things that we get wrong but could get right.

Jonathan Fields: [00:01:53] So Chip has distilled wisdom from leading research and personal transformations of thousands of people across the globe. He’s developed innovative approaches to help people really embrace midlife, not just as changes thrust upon them, but as this remarkable invitation to wholeness one that can transform fear into possibility, confusion into clarity, and stagnation into renewed purpose. In today’s conversation, Chip walks us through 12 critical insights with a lot of science and stories to back them up that have been transformative in helping to not only survive the challenges of this season of life, but to thrive in lasting alignment with really who you are authentically becoming as you move into the middle and later seasons of life. So excited to share this conversation with you! I’m Jonathan Fields and this is Good Life Project.

Jonathan Fields: [00:02:51] Ahhh, Mr. Chip Conley, it’s always so much fun hanging out with you. We’ve been doing this dance together for, I don’t know how many years at this point. I’m hanging out in Boulder, Colorado right now. I’m catching you in Baja, and you’re radiating with the glow of the sun as I speak to you.

Chip Conley: [00:03:07] Probably dangerous, right? I mean, it’s first of all, it’s great to be back with you. Yeah, I have my 12 and nine-year-old sons with me. And this morning we went. I actually went mountain biking to rappelling, ziplining, ATV’ing, surfing all before 2 o’clock. Um, so I love Southern Baja because it’s an adventure sports Mecca. And this time of year we’re cutting this, you know, the last day of July and 2024. And, you know, I’m one of the few people down here with, you know, it’s not a popular time to be down here at sort of a hotter time, but it’s, uh, it’s gorgeous still.

Jonathan Fields: [00:03:45] Mhm. Well that sounds like a pretty awesome week squeezed into like a half a day with the kids. I’m excited to dive in. You and I have been sort of like dipping into this conversation around what happens to us, to our lives, to our expectations, to the story we tell about ourselves and to the world when we start to hit the middle years of our lives. Yeah. And you keep deepening into this through the work that you’re doing with me, through just your own personal journey, which has had its own interesting moments over the last couple of years as well. And a book that is out really now diving into, and it’s the first time where we’ve had parts of this conversation in different ways, but it’s the first time I’ve seen you sort of lay out almost like a methodology saying like, these are the five different things that we really want to dip into when we’re starting to think about this transition that has no meaningful ritual or ceremony the way that so many other transitions do. So I’m curious, just to start out, what led you to the point where you said I need to actually distill all the things I’ve been doing and learning and exploring into not just a philosophy, but almost a methodology as well.

Chip Conley: [00:04:54] Jonathan, as we’ve talked about before, I struggled in my late 40s. I’m turning 64 later this year, and I struggled in my late 40s in a way that I was existential. And during that time in my late 40s, I lost. Between 2008 and 2010, I lost five male friends to suicide, ages 42 to 52. So I was having my own challenges, but then I was losing friends to what seemed like early to mid-midlife. So note to self I was like, okay, once I get to the other side of this, I want to I want to understand it more because I never really explored what midlife was. I’d done a lot of work on psychology and business, and I was an entrepreneur, but had never really tried to understand the life stage of midlife. I got to the other side. I had an NDE, a near-death experience that led me to going to the other side nine times over 90 minutes due to an allergic reaction to an antibiotic. And that was the sort of like the point at which I said, okay, I got to change this life, and I did. I made major changes in my life in my late 40s, such that by age 50, I had what Mary Catherine Bateson would call a midlife atrium, which she said was like, we have a lot more longevity than we did 50 years ago, but we sort of think as if if we’re going to have additional years in our life.

Chip Conley: [00:06:11] It’s like having two additional bedrooms in the backyard of our life, meaning we just are old, longer. And she says, that’s not true. You’re just in midlife longer. And what you need to do is create an atrium, re-blueprint your house. You know, redesign it such that you have some space in your midlife to reimagine and repurpose how you want to live the rest of your life. Because if you’re 54 years old and you’re going to live till 90, you’re exactly halfway through adulthood, 18 to 90, the midpoint is 54, and 54 is the average age of the people who come to our modern elder Academy. Me so I had my midlife atrium, which we can come back to if you want, in terms of like, how do you create a midlife atrium, what was that like, etc. it’s sort of like a gap year, sort of like a sabbatical, but it was a little bit more intentional than that. And then I ended up at Airbnb by the founders, approached me, and I spent seven and a half years there, four years full-time, three and a half years part-time, seeing what’s it like in the workplace to be not just midlife, but they called me the modern elder, which I initially hated. But then they said, Chip, a modern elder, is someone who’s as as curious as they are wise, and you’re just older than the people around you.

Chip Conley: [00:07:23] And in fact, I was twice the age of the average person there. So all of that led me ultimately to exploring midlife in a much deeper way. Writing a book called Wisdom at Work The Making of a Modern Elder, Creating the Modern Elder Academy, the world’s first midlife wisdom school. And just to sum up, six and a half years later, after having started that midlife wisdom school, I wrote a book called Learning to Love Of midlife 12 Reasons Why Life Gets Better With Age. And the reason I wrote it was because I learned from Becca Levy at Yale that when you shift your mindset on aging from a negative to a positive, which is not easy to do, but it is doable, you get seven and a half years of additional longevity, which is more life added than if you actually stop smoking at 50 or started exercising at 50. And so I said, like God, there’s so many messages PSA, public service announcements about stopping smoking and starting exercising, but there’s none about a pro-aging agenda helping people to see what gets better with age. And so the book really is 12 chapters around the social science, as well as the 5500 alumni from 50 countries who’ve come to me and me laying out, here’s what gets better with age. We know what gets worse. But let me tell you what gets better.

Jonathan Fields: [00:08:38] Yeah, I mean, it’s so interesting. I feel like the old model is okay. So we have three stages of life. You know, there’s early life, there’s midlife, And then there’s old age or later in life. And we do. We kind of look at them as like these three equal size zones. You know, you split up the pie chart so it’s all equal. And what I think is so interesting about what you’re saying is like, that’s pretty distorted. And maybe actually a generation or two or a couple of generations ago that was closer to the truth. But the way things are going now, like there’s one piece of that pie chart that is getting bigger and bigger and bigger. It’s that that midlife piece, and we have the capacity to make that potentially a lot bigger. And we don’t plan for that.

Chip Conley: [00:09:20] Well, the bigger piece is happening with longevity. The deeper, meaningful, happier part of it is not a given. And what’s really interesting, Jonathan, is, you know, when we hear the word adolescent didn’t even exist until 1904, when an American psychologist coined the term and said, like when you hit puberty, you’re not an adult. You’re when you hit puberty, you’re are in adolescence and you don’t become an adult to your 18. And so starting in 1904, you moved adulthood from 13 to 18. So like really? Is that true? Yes, it is true. That is how it used to be, because that’s why we got child labor laws. That’s why we started having people wait till they’re 18 to have kids and or get married. But prior to that, it was, you know, the teen years were sort of really early adulthood. And then once we understand that adolescence was a transitional or a liminal period between childhood and adulthood, we created a whole social infrastructure to support adolescence. Let’s be clear. Adolescence is a very difficult era to be in these days, and based upon the happiness level of adolescence, it’s not very good. But we do have social infrastructure to support adolescents, whether it’s schools, college counseling, your parents, there’s, you know, Boy Scouts, Girl Scouts, sports teams, etc. you are going through adolescence in a peer group and you’re having first experiences in that peer group, first kiss, first job, etc.

Chip Conley: [00:10:46] when you’re going through adolescence, which is a word that a lot of people are not familiar with, but it is an academic word to describe midlife. It’s the time of life when you’re going through hormonal, emotional, physical, and identity transitions, much like you are in adolescence. But we have no social infrastructure to support people through this middle essence period, and therefore we end up with people who feel like they’re getting the game of life wrong. And there’s not really a roadmap or any kind of like highway signs to say like slippery when wet or, you know, you’ve got a U curve coming around, you know, in a moment. So long story short, is what I really wanted to do was to help normalize some of what happens in midlife so that people can understand the transitions that happen in midlife, how purpose evolves, how your sense of ego and soul evolves, and how you have the ability to grow wisdom and most importantly, help people to see that there are things that get better with age. We should jump into some some of what those are because I want to do a what do you call a class action lawsuit against hallmark cards? Um, because starting around age 40, hallmark reminds everybody what gets worse with age, but they don’t actually remind us what gets better with age.

Jonathan Fields: [00:12:06] Let’s dip into that then, and maybe we’ll use your frame of these five different buckets. Zones. What how do you describe them actually.

Chip Conley: [00:12:13] So there’s really five different areas okay. There’s the physical the emotional, the mental the vocational and then the spiritual.

Jonathan Fields: [00:12:22] Great. So let’s start out with the physical then, because I think this is the one that so many of us are focused on as we age. Like we’re looking in the mirror, you know, and we’re feeling in our bones, we’re feeling in our muscles, we’re feeling the physical changes. We’re seeing the physical changes and culturally and societally. And granted, I’m speaking more about a Western culture because I think this is different in different cultures. It’s much more acceptable and even celebrated. But at least in Western culture, often all of those things that we see and feel on the physical life side of things are the things that we’re told are wrong, and that we should do everything possible not to see and feel.

Chip Conley: [00:13:00] Yeah, to start with, the physical, as the first of the five was a bit of a challenge because it is where the ageism is most evident, because when you’re going to be, you know, when a tree gets older, it has rings and you can count the number of rings, but you have to go inside the tree to find it. When a human gets older, you count the number of wrinkles and it’s on the exterior. So we age publicly, and we do live in a world in which aging is thought of as something that is a physical manifestation. We’re growing and we’re aging our whole life. We’re aging at age three. You don’t tell a three year old, oh, you’re aging now, you say. They’re growing, but you also don’t tell a 75 year old, oh, you’re growing. You’re not aging. The truth is, they’re the same thing. It’s just that when we talk about aging, we tend to be talking about as we get older. It’s about the physical manifestation of aging. So the first two things that get better with age, number one is a lot of people just don’t realize how much longevity they may have when they see some chart that says the average American lives until age 78. They think, okay, well, I’m 62, I’ve got 16 years left. But the reality is, if you’ve already gotten to 62, you’re going to live longer than than 78. Because guess what? You’re not one of those people who died before age 62. Additionally, depending upon socioeconomic factors, education, etc., you’re likely to live longer.

Chip Conley: [00:14:28] So the first thing that gets better with age is, you know, you have more life ahead of you than you think you do. So that’s an important thing. Why is it important? Because actually, if you have more life ahead of you, you can actually sort of live it as if you’re not just running out the clock, so to speak. If at age 54, you realize you have half of your adult life still ahead of you, maybe you’re going to take up something new. Maybe you’re going to become a beginner. One of my favorite questions to ask people is ten years from now, what will you regret if you don’t learn it or do it now? Because becoming a beginner at something, especially if you know you have a longer life still ahead of you, is important. And frankly, that’s how I learned Spanish at age 57. And I learned how to surf at age 57 because it was not going to be any easier living in Mexico to learn those things at 67. So so that’s the first one. The second one is like taking head on just the idea of your body. You know, your body is a rental vehicle. You are issued at birth. And the question is, and by the time you get to my age, it’s Hertz rental car. My body hurts, But no, the idea that it’s, you know, you have been issued a rental vehicle and your job is to maintain it is key. But what happens early in our life is we’re waxing, you know, we’re waxing the car and making it look beautiful.

Chip Conley: [00:15:47] And there’s a point at which you have to sort of say, like, you know, it matters more what it feels like on the inside of that car than what it looks like on the outside. And that doesn’t mean we should let our body fall apart. It just means that we should focus more on long term maintenance than short term vanity. And it takes, you know, a six pack gets more expensive as you get older. And what I mean by that is they’re not charging you more at the liquor store. It’s just that actually maintaining a six pack for your abs is harder to do. So if you want to spend more time, you know, working on it, that’s great. But just be careful of knowing how much of your time is being invested in just your physical form. So helping people to see that, you know, they that their body doesn’t have to define them anymore. This is particularly true for women, whether it’s learning to be comfortable going gray with their hair or realizing that they’re okay with a little bit of a rubenesque, you know, figure that is not trying to be so skinny as they used to be. So this is a really important one, because if you think the only playing field of life in terms of how you will be judged in life is what you look like, my God, what a difficult life you’re going to have. As you know, post age 50. Yeah, or even post age 40.

Jonathan Fields: [00:17:03] I mean, it makes me curious also, because we have right now, we’re sort of we’ve got four generations semi coexisting like Z, like millennials, Gen X and boomers.

Chip Conley: [00:17:13] Well, you got silent generations beyond that too. I think Joe Biden, if I’m not mistaken, might even be. Yeah I think he’s a silent.

Jonathan Fields: [00:17:19] The greatest generation. Yeah.

Chip Conley: [00:17:21] Or greatest whatever. Yeah.

Jonathan Fields: [00:17:22] So the younger generation, you know, like my I’m an actor and I grew up and you know, I’ve learned technology because technology is part of the way. Or am I living? It’s how I communicate. It flattens the world for me, it’s amazing. And at the same time now we have younger generations who are, quote, digital natives who have also grown up in a world where they have just constant nonstop access to comparison of everybody’s life on the surface, everybody’s physical appearance on the surface. I sometimes wonder what happens when generations that have basically learned to value almost everything in their lives through comparison hit this age that we’re talking about and start to realize, is it a completely different experience for them? And I guess we won’t know for a while, but it concerns me.

Chip Conley: [00:18:12] Well, here’s what we know, Jonathan. There’s this thing called the U-curve of happiness, which has been in place for 15 years, but it’s changed recently. The U-curve of happiness basically showed that starting around 22, 23, 24, your life satisfaction as an adult starts to decline slowly and it bottoms out around 45 to 50. And then at 50, things get better with each decade after that. So it’s a u-curve and it’s 45 to 50 is the low point sort of classically midlife. But the recent research shows that actually young people, young adults are unhappy starting at age 18. They’re like lower happiness than of 45 or 47 year old. And so instead of being a u-curve of happiness, it’s almost like a growing incline of happiness. So it means like, okay, there’s no u-curve because you didn’t actually sort of fall into midlife. You actually started at a point of life satisfaction even below that. And a lot of that comes back to social media. I mean, so much of it does and so much of it comes to, you know, comparison is the recipe for suffering. And we have created a product in with social media that has in many ways created a vehicle for people to constantly be comparing their insides with other people’s outsides. This is particularly pronounced for younger women. Long story short is I think we actually the data’s already in us. And so I think what’s going to be interesting to see is, over time, as we may figure out how to tame the excesses of social media, do we go back to the classic u-curve, which has also been found in apes? I mean, and also in some primates. So they have not had the problem with social media. So it’s the u-curve still exists for apes.

Jonathan Fields: [00:19:59] And we’ll be right back after a word from our sponsors. So here’s my curiosity, right. Because you’ve had some 5000 plus people through your programs over the last chunk of years, right? And these are generally people where you save like 45 to 65, 75 ish. Yeah, 45.

Chip Conley: [00:20:14] To 65 is 75% of them fit that age range. But we’ve had people as young as 25 and as old as 91.

Jonathan Fields: [00:20:20] Okay. So when these folks show up and they’re sort of like immersed in an experience which says, hey, listen, I really want to take a look at my life. I want to understand where I am now and start to really think about the future. Are you seeing what you’re describing as the data coming in for, for for younger folks now? Are you seeing that showing up in the people that you’re working with on a regular basis also? Or is it you feel like it’s not as apparent, like it’s easier to disconnect?

Chip Conley: [00:20:47] What is showing up.

Jonathan Fields: [00:20:48] The measuring their life where they’ve been, and even thinking about where they’re going through technology that really brings a ton more comparison into the process.

Chip Conley: [00:21:01] Yeah, there’s no doubt we see it. What I would say is that it’s more the people who are more afflicted by it are those who are younger. And so it’s it’s more our millennials who come to the program than it is our Gen Xers or Boomers, but also the millennials who get who come to a program called the Modern Elder Academy are probably a little different.

Jonathan Fields: [00:21:23] They’re self-selecting. They’re little.

Chip Conley: [00:21:25] They’re self-selecting. They’re sort of focused on wisdom. And they’re. They generally. I mean, there’s some really wise 35 year olds out there, which makes me feel good. But, you know, the idea of comparison, we’ve been doing this comparison thing forever. Consumerism. I mean, consumerism as a word, is 70 years old, but there’s a word that we’re popularizing at me called success ism. And success ism is not comparing yourself with the Joneses next door, consumer wise, but you’re comparing yourself with your parents or your community’s expectation of what defines success. And that’s incredibly toxic. That is not so much just from social media. That’s from just buying into the belief that somehow someone else is defining the script of your life, and the wake up call a person has when they realize that, you know, the ladder they’ve been climbing has been on the wrong wall, and maybe they shouldn’t be even climbing a ladder anyways is a real revelation for people when they come to a program like ours. And they may have had what happens to a lot of people in midlife is they hit an age. Sometimes it’s age 50 and they’re like, oh my God, I’m disappointment equals expectations minus reality. They’re fraught with disappointment because they had some expectations in their life that they’re going to, you know, marry their soulmate, that their kids were going to go to Ivy League schools, that, you know, they would be president of the United States, whatever it is. And they’re they’re now seeing the future and they can realize, okay, at age 40, they still had hope at age 50. They didn’t. And then they but they also then have to start to ask the question of like, were these things the right things that matter and that I should be caring about? And so so that’s actually so yes, we finished the first one physical.

Chip Conley: [00:23:08] Let’s move to the emotional one, because the emotional starts to get into some of the things I just mentioned. So there are three reasons why life gets better with age in this category. The first one is emotional intelligence. This data is really conclusive, and it shows that on average, our emotional intelligence grows with age. Most importantly, our emotional moderation grows as well, which means we’re not as reactive. You know, Viktor Frankl famously said in, You know, man’s search for meaning between stimulus and response, there is a space in that space is our power to choose our response. And in our response lies our growth and our freedom. Somehow, for many people, the ability to be less of the monkey mind, less of the pinball and the pinball machine starts to kick in in one’s 40s and 50s in particular. So we learn how to dance with our emotions. We can identify our emotions more. You can actually instead of saying, I feel good right now, you can be more specific and understand, you know, the content of an emotion. So that’s helpful because learning how to dance with your emotions is like Rumi’s guest at the guest house poem, where you just realize these emotions are coming through me and my job is to be a great host hotelier for my emotions, but recognize that they can check out. They don’t have to squat. So that’s the third. That’s number three on the list of 12. Number four is investing in our social wellness. We were talking before we went on air about the fact that Bob Waldinger’s book. You know, he stole your title of your podcast.

Jonathan Fields: [00:24:41] It’s okay. He has my blessing.

Chip Conley: [00:24:43] Yeah. He’s a wonderful man. So Bob has been running the Harvard study on adult development that’s been going on for 86 years. And he said conclusively in his book, The Good Life that came out last year, the number one variable for happy, healthy, long-living people is how invested are they in what he calls social fitness, what I call social wellness in midlife and beyond. And so how we think of friendship as a practice. And we have Mark Nepo, the great poet who teaches at MBA twice a year, and he has a whole workshop on the power of friendship and how to learn how to think of friendship as a practice. And it’s a beautiful workshop because it’s like, wow, friendship as a practice. I’d never really thought of that before.

Jonathan Fields: [00:25:30] And as adults, I think adults like when they think about friendships, they kind of feel like I hit a certain point. I kind of have who I have. And it also becomes really intimidating, you know, trying to figure out, okay, so who else might be fantastic to bring into my circle to become friends, maybe even at some point. Chosen family. And we don’t participate in sort of like activities and rituals and experiences that make that organic to us. So rather than saying stepping into a container where like this is created for us, which makes it, I think a lot easier for a lot of people especially, I’m raising my hand as an introvert, right? And a sensitive person. And if those containers aren’t sort of created for us or we don’t seek them out, then we just kind of sit here and be like, I’m okay. And oftentimes we’re not. Yeah.

Chip Conley: [00:26:15] Let’s talk about rituals for a moment, because rituals are you know, I write about it in the book. They’re incredibly important. And when you’re actually going through the three stages of any kind of transition, there’s usually the ending of something the messy middle and the beginning of something. And, and we have lots of rituals and rites of passage younger in life, you know, we bar mitzvahs, bat mitzvahs, baptisms. You’re going to have a commencement address at your high school graduation, you’re going to get married, you’re going to have a baby shower, etc. but you get to midlife and there’s nothing. There is zero. And so learning how to actually establish rituals in your life and build them, it’s important. A ritual is different than a routine. Malidoma Soma, wonderful African writer who’s recently passed away, used to say that the difference between a ritual and a routine is in a ritual, you are open to being altered. So how do you create an empty nest ritual? You know your friends who are also becoming empty nesters. And you remember Ferris Bueller. When Ferris Bueller’s parents went away, he had a party with his kid, with his high school friends. What if you had a party when you all of a sudden you’re an empty nester and you get four couples together, and once a month you have an empty nester party? If you’re going to get divorced, why not have a divorce party? You’re with your spouse or without your spouse, but do something that’s got a ritual attached to it, because that community support is really what’s at the heart of this. Fourth reason is you start to value your personal and social relationships more.

Chip Conley: [00:27:45] Unfortunately, for a lot of men in particular, their friendship muscle has atrophied and therefore they don’t really try. And then we wonder why we have the loneliness epidemic we have. So that’s the fourth one. The fifth one. On the reasons why. 12 reasons why life gets better with age is I have no more F’s left to give f-u-c-k basically. It doesn’t mean like you’re an angry person on the front lawn of your home with a gun saying, stay off my lawn. That’s not what we’re talking about here. We’re talking about when you actually realize what you care about and what you don’t care about, and you start to get to a place in midlife where you realize there’s a bunch of things that you used to care about. You don’t you shouldn’t be caring about anymore, including what other people think about you. Yes, care about certain people and what they think of you, but not everybody. And don’t sweat the small stuff. So there’s a point at which you start to realize, okay, Mark Manson, his book sold like 20 million copies, and it was all about learning what to not care about. And this is a really important one, because some of the people who have the hardest time in midlife are the ones who are still people pleasing, like they did in their adolescence. I’m one of those people I you know, it was in my 50s that I had to really get used to the idea that I, that I needed to be a lot more discerning about who is renting space in my brain.

Jonathan Fields: [00:29:10] I think part of that also is, you know, like when you start to say, like, I really can’t, these things just don’t matter to me in any meaningful way, other than the fact that it seemed to be spinning them in my head. Yeah. When you do learn to let go of them, it frees up a certain amount of bandwidth for you to then ask yourself, what does matter to me right now? Right. Like, how can I reallocate this energy to something I genuinely care about, or to some one or some community I genuinely care about and I want more of in my life? But when when those things that really don’t matter but seem to be just sitting in your brain and taking up 12.8% of your cognitive and emotional and creative bandwidth, that’s bandwidth you can’t use for things that would actually really bring you to life.

Chip Conley: [00:29:50] And this is where we have to take a proactive stance on it, because sometimes it’s hard. Sometimes it’s really hard to sort of say, okay, I’m not going to care as much about that anymore, or I’m not going to spend as much time with those kinds of people, etc..

Jonathan Fields: [00:30:03] That brings us to The Mentalist.

Chip Conley: [00:30:04] Yeah, the first one is the mental number six overall is about wisdom. And it’s really that, you know, our painful life lessons are the raw material for our future wisdom. So the more life we’ve experienced, the more lessons we’ve had, the more experiences we’ve had, the more raw material for wisdom we have. That doesn’t mean we’re wiser. We know 30 year olds who are wiser than a 70 year old, partly because they’ve metabolized their experiences more. So, what we know is that the raw, material life lessons are the raw material for creating your own wisdom based upon that experience. Arthur Brooks and his book From Strength to Strength, in which he profiled me, the Modern Elder Academy, talked about crystallized and fluid intelligence. And based upon the research that’s been done, it’s shown that like fluid intelligence, where your brain is fast and focused, it can solve things quickly, is the domain of people in their teens, 20s and 30s. But crystallized intelligence, the ability to think systemically, holistically, and connect the dots is something that we do better as we get older. In fact, it peaks at around 70 to 75. And that’s being able to sort of see the big picture. And part of the reason for that, doctor Gene Cohen has shown is that you have four wheel drive of your brain. The older we get, the more we can move more adeptly from left brain to right brain. And that means we can think sort of more systemically. And so being able to have some wisdom and marveling at the fact, like, oh my God, how did I have the right answer to that? I didn’t think about it. It just sort of came up intuitively. That is what happens as we get older. We don’t have to dwell on something. We just can have a little more trust that we have the life experience that’s going to help us to make good decisions. So here’s my.

Jonathan Fields: [00:31:48] Question on that. As you said, and very rightly so. Like there are plenty of 30 year olds who are wiser than 70 year olds because it’s not just about the experience, it’s how you’re using your language. Metabolize them. Yeah, I feel like a lot of folks have actually lived their lives with their heads down. Of course, you know, like I’m doing the thing, like following the track that was laid out for me. I’m checking the boxes. Right? I’m having the experiences. They’ve got this growing data set to draw upon, you know, like, from which to derive ideas and wisdom and perspective. And yet it doesn’t happen readily. And I’m wondering, for somebody that actually has that data set to draw on, but they’re not there. It’s like compartmentalised over here. And I think a part of that for a lot of folks also, is the fact that we’re never really taught the skills of self-awareness, self-inquiry of self-discovery. Do you have a sense for like, what an unlock key is for somebody who’s saying, okay, so how do I turn this switch on? How do I take all of this data and start to metabolize it?

Chip Conley: [00:32:47] I’m going to show you this is I don’t know, you can’t probably can’t read that, but it says my wisdom book. January 1990.

Jonathan Fields: [00:32:53] Got it. For our listeners, Chip was just holding up a journal.

Chip Conley: [00:32:57] Yeah. Here’s my wisdom book number seven. Got it. Long story short, is there’s something I’ve been doing for 35 years now, and I had no idea when I started doing it. It would be something I’d be talking about many years later. But when I was, I started my boutique hotel company called joie de vivre at age 26. And by 28, when you’re 26, you’re starting a company like that, like you don’t know what you don’t know. By 28, I knew what I didn’t know, and I realized I didn’t. I didn’t know a lot of things. So one Friday afternoon, I was I limped home from work and just said, like, oh my God, I don’t know what the hell I’m doing. And I took a journal off the bookshelf and wrote on the cover of it, this one here, my wisdom book and I started to practice. I’ve been doing for 35 years now. Every weekend I sit down for 20 to 30 minutes and I make a list of bullet points of what were my key personal, professional, spiritual, physical lessons of the week. What did I learn this week? It could have been somebody I hired and like, it’s not working out. And you know, what were the lessons? And then how will that lesson serve me in the future? What’s the lesson? How will it serve me in the future? And that’s the practice. Practice is 20 to 30 minutes every weekend. Reviewing that and what you’re really doing is you’re metabolizing your experience more quickly. You are cultivating and harvesting your wisdom. So I do this. I did this at joie de vivre with my team. I did it at Airbnb when I was helping to helping the founders run the company, and I’ve done it here at me.

Chip Conley: [00:34:25] And the practice is this once a quarter, I sit down with my leadership team. You can do this with your family. If you have an extended family, you could do this with, you know, a nonprofit board you’re on whatever it is. And I sit down and I say, what was each of us? Let’s talk about what our biggest lesson of the quarter was. And with the leadership team, it’s not awkward, but it’s a little unusual because you’re talking about the thing that may have been your biggest mistake of the quarter, or the thing that really bothered you, or what you’re supposed to do is talk about the thing that was difficult, what you learned from it, and how it’s going to serve you in the future. The beauty of it, Jonathan, is by having all of your leadership team do that. Not only am I learning my lessons, I’m learning your lessons. So wisdom is not taught at shared. And when it’s shared, I’m wiser as a result of that. And then we end the meeting. This is a quarterly meeting with a conversation about what was our biggest team lesson of the quarter, and what’s it going to do, how is it going to serve us in the future? So I think we’re living in an era where we’re moving out of the knowledge era and into the wisdom era, and I mean that partly because all of the world’s knowledge is on this little iPhone I have on my pocket. And with ChatGPT and AI, our knowledge is like a commodity. What’s valuable is what’s scarce, and that’s wisdom.

Jonathan Fields: [00:35:45] Yeah, I’m just thinking, as you’re describing that, how cool would it be to do this exercise on a quarterly basis with with family or chosen family? Right. If you’re fortunate to have kids, if you’re blessed to have parents still with you like. And everyone’s there to. I mean, how fascinating would it be to actually gather three generations, maybe four generations together, or maybe it’s two generations, whatever it is, to actually have this transfer and sort of collective realization.

Chip Conley: [00:36:12] If people want to go to generations over dinner. Com that is a website that we created two years ago to curate, like Jeffersonian dinners amongst the generations and talk about, you know, your lessons, but also specific to particular topics like societal problems, purpose, love and relationships, etc. so yeah.

Jonathan Fields: [00:36:30] That’s awesome. Let’s drop into the next one.

Chip Conley: [00:36:33] The next one is number seven on the overall list is I understand my story, you know, my life narrative. And that is true. You know, when you’re a quarter of the way through a novel, it’s hard to know the characters or the themes, but when you’re halfway through the novel, you understand the characters and the themes really well. And why is that important? Well, then you can start plotting your own hero’s journey. And if our heroine’s journey, or I like to call it, just the human journey. And it’s important to understand your hero’s journey, because the hero’s journey helps you to understand the shadows in your life. It helps you to understand what are the things, the pattern recognition of how you make the same mistake over and over again. Understanding your narrative means you are self-aware and self-reflective, and then you can make proper changes in your life. But people who are not self-aware and self-reflective don’t necessarily see their shadow, and therefore they just keep repeating the same mistakes and they complain about the new boss or the new spouse after they jilted the old spouse or old boss spouse. And yeah.

Jonathan Fields: [00:37:34] The one thing I love about that also is that I mean, this is if you think about reading a novel, right, you get a certain way into a novel where you’re far enough in so that you’re starting to figure out some cool things. And then there’s like the foreshadowing. You’re like, wait a minute, that thing that happened on page 23, and then that other thing that happened on page 58 like that actually. Now I see how it all goes. And then, and I feel like when you get to a certain point in your life also, you can look back and see the foreshadowing in your own life and you’re like, oh, wow. This revealed so much about my story like 20 years ago. And now I’m like, now I’m finally grokking like where it fits into the story.

Chip Conley: [00:38:12] Yeah, I mean, Jonathan, you just described the wisdom that, you know, so that’s why these two fit well together. Because, you know, once you have some wisdom, you can start seeing your own patterns. And then the eighth one overall, the third one in this section on mental is editing your life. You know it. The first half of your life is about accumulating. The second half of your life is about editing. And that’s really important because if you’re running the mid-life marathon and I believe that mid-life lasts 40 years now 35 to 75, if you’re running the mid-life marathon and you’re not letting go of some baggage along the way, man, that’s tiring. So learning how to it’s sort of similar to the thing about I have no more F’s left to give, but it’s a little different. It’s really being much more intentional about understanding what are the mindsets, what are the identities? What are the archetypes? What are the grudges that I’m ready to let go of? And we do something at me that I talk about in the book, which is the great midlife edit, which is how do you ritualize the process of letting those things go? Let me use an example.

Chip Conley: [00:39:18] I mean, I, I have a resentment toward somebody from 20 years ago, and I have not let it go. And I know that. And it’s not like it’s changed my life dramatically for the worse, but it’s just something that I need to let go of and just sort of say, like, you know what? I need to let go of what I feel jilted about something. Similarly, it could be I have a mindset that I always have to be the caregiver in this family, but I’m not very good at caregiving myself, and it doesn’t mean you have to go the opposite. It just means you need to dose it down. And so how do we start to look? We can have a mindset of I’m too old to start a new business, or I’m too old to meet my soulmate. I mean, there’s there’s a lot of things to edit in our lives, and to be able to be very intentional about the mindsets or limiting beliefs is really an important thing to do in midlife.

Jonathan Fields: [00:40:08] I found that so powerful. Also, I wrote an essay not too long ago called The Last Line, and it was really just this notion that a lot of the early part of our life is about accumulation, and then we reach this moment where we sort of like we step over the last line, and we often don’t know when it happens, and sometimes it’s more of a, it’s a field than, than a line. But there’s a shift that happens and it’s just about it’s not about accumulation anymore. It’s about streamlining. It’s about lightness, you know, and it’s so powerful when you find yourself in that space, because just the energy of accumulation is so different than the energy of shedding and lightness. It brings so much space to your days.

Chip Conley: [00:40:49] We have some language for this for people later in life, especially empty nesters. We call it downsizing, you know, and people downsize their home from a four bedroom, ranch style home to a two bedroom condo in the city. But how might you downsize your ambitions? How might you downsize your way of thinking about your to do list? How might you downsize your friend list so that your focus more on quality than quantity, etc.? So that’s the final one in the third category. So let’s go to the fourth category, which is the vocational life. The vocational life. The first one on this list is and blessedly jumping off the treadmill. And that really comes from the idea that success is in which I talked about earlier. You know, David Brooks famously in his book The Second Mountain, talked about the the first mountain in life is success. The second mountain is purpose. And what he was really speaking to is the idea of like, at some point you realize that the thing you’ve been pursuing was really not the thing that was most important to you. And as we get to midlife, we start to get really clear on how we want to define success and what what is our sense of purpose in life. And then there’s a big P purpose and a small p purpose. The big P purpose is the kind of thing that you’d have on your LinkedIn profile. The small p purpose is the kind of thing that someone would talk about at your eulogy. So long story short, is to be able to get off the treadmill that wasn’t your treadmill, it was somebody else’s. There’s something wonderfully blessed about that because you didn’t realize you were on the treadmill.

Jonathan Fields: [00:42:27] That’s the whole thing right there, right? So, and even if you did often, you don’t realize it’s not your treadmill. Even if you’re like, oh yeah, like, I’m on this thing and I feel it and my calves are burning and my shins are healing, but I’m like, I know why I’m at this speed and this incline. And then you get to a point, you’re like, wait a minute, that treadmill three treadmill is over. That’s a lot. And maybe it’s like, I don’t want to be on a treadmill anymore.

Chip Conley: [00:42:50] That’s why I sometimes have a hard time with David Brooks, with his, like, okay, you know, the second mountain? Well, what if it’s not a mountain? What if it’s like a a lake? Or what if it’s like walking along a stream or, you know, for you, Jonathan, you moved during Covid from New York to Boulder. And sometimes we have to change our habitat to change our habits and to change our mindset. I definitely think that people really need to consider sometimes in this blessedly get off getting off the treadmill to actually say, you know, do I have to change my habitat as well? Because that sometimes is part of the problem?

Jonathan Fields: [00:43:24] Yeah, and it’s kind of like what you said earlier also about the latter. Like there’s that classic versions of like, well, maybe you climb a ladder and you realize it’s leaning against the wall and it’s not yours, but maybe like, you don’t want to be climbing any ladder at all. Maybe it’s less about pursuit and more about unfolding. And that’s actually an okay thing.

Chip Conley: [00:43:41] Pursuit of happiness is so woven into our psyche. And yet the word pursuit in some dictionary says to chase with hostility. Do we chase happiness with hostility?

Jonathan Fields: [00:43:53] It feels like. Right?

Chip Conley: [00:43:54] We certainly do at the mall at Christmas time. But, um. Uh, so the next one in this category, the 10th one overall, is time affluence. Oh my God, this is one that I of all the 12, it’s the one I’m the worst at. And it’s the one I care and love the most to actually have. Time. Affluence. To realize that to be rich is with money. To be wealthy might be with time, and to realize that once you’ve stepped off the treadmill, maybe once you your kids have left home, maybe once you have actually stopped pursuing, you know, and being so focused on attainment and more focused on attunement, you have actually created some space in your life to be curious. Oh my gosh, I have space in my life to be curious. And then the question becomes, what can I be curious about? So when I did my midlife atrium between 50 and 52, I was really curious about hot springs. I wanted to understand the geothermal side of hot springs and and experience hot springs all over the world. I was really curious about emotions, and I ultimately wrote my book, Emotional Equations, because of that. Because in my late 40s, I was so emotionally blocked up and confused and not emotionally fluent that it really hurt me as I was going through all the difficult times I was going through. So I wanted to really understand emotions better, and then I wanted to understand festivals.

Jonathan Fields: [00:45:16] I remember that season of yours. Did you go to like 300 festivals around the world or something?

Chip Conley: [00:45:21] Founding board member of Burning Man board. And I was curious why, in a world in which we the more digital we get, the more ritual in the form of festivals, collective effervescence we need. And so I went around the world for two, couple of years. In fact, in one year I went to 36 festivals in 16 2016 countries, and created a list of the 300 best festivals in the world. And, you know, had that little, little sort of passion business for about three years. But yes, having time affluence gives us space. And in my case, I got very intentional about how I used my space, which then became like, okay, well, that was the new thing on my calendar. Like, okay, how about just listening to Rickie Lee Jones in the hammock in the backyard? Chip, how about that? That’s I’m still learning. So so but I think time affluence is just huge. It’s a really important piece of getting older and not being scared of an empty calendar. I got to tell you, I try to do the Sabbath one one Saturday or Sunday per month. That’s all. I have a day that is my Sabbath and that is the day I have nothing on the calendar. I have no one I’m going to see. I’m by myself, usually with my dog in nature, and my job is to ask the question, nature, what do you have to teach me today? And that’s my favorite day of the month.

Jonathan Fields: [00:46:46] Yeah, I love that. It’s such a great practice. And I love that you’re also saying, okay, so we struggle with this. So maybe don’t lock yourself into okay, I’m going to do this every single week because sometimes we have to grow into that maybe like a half a day or like three hours on a Saturday morning. Once a month is something that we can start to commit to. Like first, just commit to the container for it and then over time, just like, give it the fuel, give it the space to just grow organically because you start to realize, oh, this actually feels pretty good.

Chip Conley: [00:47:16] Agreed, I love it.

Jonathan Fields: [00:47:18] And we’ll be right back after a word from our sponsors.

Chip Conley: [00:47:23] All right. Let’s go to the last category which which is spiritual. And the number 11 on the total list. Number one in this category is just about I’ve discovered my soul. For some people, literally, it was a guy in one of our Me workshops. At the end of the workshop he said, you know what? He said, normally on a vacation I go sightseeing, but here at me I go soul seeing. And he was like, I didn’t even realize I had a soul. And so the you know, Richard Rohr, who just last week taught at our Santa Fe campus and is an MBA alum also, but he’s also on our faculty. He says that the first half of our life, our primary operating systems, are ego, and we get really acquainted with it. We overuse it and we overidentify with it, but it is our thing that individuates us and helps us to propel ourselves forward and show up in the world. But it is around midlife that actually the ego structure starts to disintegrate. And it’s often things, the circumstances of our life where shit happens that actually sort of like you have a dark you, we call it the dark night of the soul, but it’s really the dark night of the ego and some of the way, and Brené Brown calls it the midlife unraveling, where we have a Ravel of our expectations and the way we live our life, and it’s starting to unravel, and it’s really good.

Chip Conley: [00:48:49] It’s unraveling. It’s a good thing. And yet if you your ego structure can’t handle it, it’s a problem. And this is when often we get acquainted with this thing called the soul. If we weren’t familiar with it earlier. And it’s this part of us that actually feels often in our solar plexus or in our gut that feels like it’s very centered. When you feel good and it feels like it’s connected with spirit. So soul and spirit, soul maybe inside yourself, spirit potentially outside of yourself, something bigger than yourself. And it’s this connection and soul is also potentially connected to your past lives or whatever it is, that it’s connected to something much bigger than your brain. So when people actually start to realize that and see the power of the soul, and the fact that there’s an alternative way of looking at their life. It’s a revelation and we call it the Baja aha! At our Baja campus, it’s like an epiphany. And that is really something that happens. And there’s a lot of social science research on this that talks about the curiosity that people have around mystery, the curiosity around mystery, the curiosity around meaning and purpose that really starts to foment in someone’s midlife.

Jonathan Fields: [00:50:03] Yeah. And I’m curious what your take is on this. I feel like sometimes we hit that point and we’re like, oh, wait a minute. I’ve lived the last 50 years of my life predominantly through ego, and I’ve just, quote, wasted it rather than saying, you know what? Actually, that ego has got me where I am. Totally. Not all of it, but it saved me when I needed to be like, you know, dealing with something it allowed me to do to survive certain things. It allowed me to create or build certain things. It’s not that it’s a bad thing, it’s that there’s no shame around the fact that we have an ego and we’re never going to fully jettison ourselves from ego. And that’s not the not the point. No, no, no. I feel like sometimes we shame it and it’s like, no, it’s actually served a really important purpose in getting us where we are now. Let’s just take a more expansive view of what matters.

Chip Conley: [00:50:49] That’s exactly right. And here’s my metaphor that I love around this. So I went to I went to ballroom dancing school in sixth grade. And so as the boy, I learned how to lead the girl in ballroom dancing school.

Jonathan Fields: [00:51:02] Please tell me there’s video of that somewhere.

Chip Conley: [00:51:03] Oh my God. I mean, I don’t think it happens anymore. I don’t think this is. But this shows how old I am. So ballroom dancing school. I’m leading the dance. When I think of this in the form of ego and soul, it’s like the ego is leading the dance the first half of your life, and then it’s around midlife that actually the soul starts to lead the dance, and the ego has to learn how to go backwards and in heels. And going backwards and in heels is not easy for the ego. So the ego has to have a sense of humor. When I put it in that framework and I thought like, ah, how can I have a sense of humor about my ego? And to actually see that my ego is not used to being led by the soul? That helped me so much. And this is not about disavowing the ego, or to feel like it did not have an incredibly important role in our lives. It just has a diminished role. It still has a role. And then the final one on this list, number 12, is instead of just learning how to grow old, we’re learning how to grow whole. And I love this one because when you hang out with someone who has presence and is 75, 85, 95 years old, what you notice about that person is that they are alchemically whole.

Chip Conley: [00:52:20] They are not compartmentalized. They are in being present. They feel like they have Somehow taken all of these constituent parts of who they are and who they’ve been, and how they’ve lived their life and woven them into this potent mix of this human, I believe, and I’ve seen it in my own life, that as we get older, we become alchemists. We take the introvert and the extrovert and we sort of combine them. We take the curiosity and the wisdom, the gravitas and the levity. Gravitas being depth, the levity being, you know, lightness. And we take the masculine and the feminine and the people who we most admire with their aging process and growing into who they are growing whole, are those people who are able to take those polarities and make them. One long story short is that is the sort of the the crescendo to my mind of these 12 reasons why Life gets better with age. Because you get to that stage. There’s a radiant being that you have become.

Jonathan Fields: [00:53:30] Yeah, and maybe I love this. Sort of like the five different lives and the 12 different ideas, because I’m smack in the middle of all this, and I’m thinking about it all day, every day, and trying to live into it in a lot of ways. But also it’s just there’s a sensibility to it. There’s an ease. It’s like, oh, okay, so this is the stuff and this is the general map. And now I get to create the territory of my own life. But this helps a little bit. So somebody listening to this and they’re sort of like somewhere in that in this middle season, what big invitation would you make to them right now?

Chip Conley: [00:54:03] The invitation I would offer is curiosity. First of all, know that what you’re going through in midlife is common. Probably I don’t know what you’re going through, but there are so many transitions that happen in midlife that so many of them are common, whether it’s empty nest or divorce, getting fired, having your parents pass away, having a health diagnosis. That is a shock. And just know that you’re not the only one. And that there are these three stages of transitions that we call it the anatomy of a transition. For those who want to learn more about it, there’s a free resource on the MBA website called The Anatomy of a transition. At the bottom footer of the website. Just click on that and you know, it really gives you some coping mechanisms of how to go through midlife. But I would also just say be curious and have a sense of humor about this period. Because on the other side of this challenging time, you are going to be a wiser person and maybe one who has a different point of view and perspective. We had a woman who came to me recently, and she’s a divorce attorney. I mean, she was a litigation attorney. She hated it. She hated the last ten years of life. She was 60 years old. She hated her 50s because at 50 years old, she realized she didn’t want to be in litigation anymore.

Chip Conley: [00:55:20] She had to wear armor all day long in terms of her work, and. But she stuck with it for ten years and like, just because she didn’t know anything better. And at age 60, she said, I can’t do this anymore, but I still have to work. And so she came to me thinking, okay, I’m going to become a litigation consultant. But that’s like swimming in the same pond. And by the end of the week, she came to realize that she wanted to be a pastry chef. And the reason she learned that was because she, during the week, had heard me say something, which was that often your purpose is something that you are excited about, agitated about, curious about, or something you’ve neglected from earlier in your life. And she had these dreams in the middle of the night about her grandmother. And and she used to cook pies with her grandmother and her grandmother’s kitchen. And she realized that, like when she would go and travel somewhere, the first thing that she would do is look on her digital map for the closest bakery. And and she realized that she loved having friends over for dinner, and mainly because she wanted to cook, cook pies or cakes. So she realized that.

Jonathan Fields: [00:56:21] It’s like the tales are all around you. That’s right.

Chip Conley: [00:56:23] They’re all there.

Jonathan Fields: [00:56:24] Oh, wait a minute. That’s exactly.

Chip Conley: [00:56:25] Right. But she. It was so far afield from litigation that she didn’t even know it was a possibility. So one of the most important things we need to really open up to in midlife and beyond is we have more choices than we think we do. And the key is to find the habitat, whether that’s an MBA workshop, whether that’s a coach or a therapist, whether it’s hanging out with a group of friends once a month to ask deep, meaningful questions. We need to be with other people who can objectively help us see ourselves, but also who can help us see what choices we have.

Jonathan Fields: [00:57:02] Mm, I love that feels like a great place for us to come full circle as well. So I’ve asked you this question I don’t know how many times, but but I’m going to ask it again because we grow, we learn, we metabolize our our data set in this container of Good Life Project.. If I offer up the phrase to live a good life, what comes up.

Chip Conley: [00:57:20] At this stage in my life, to live a good life is to serve. I didn’t I didn’t say serve, I said serve, serve. Erik Erikson, developmental psychologist, said, I am what survives me and that is what we should be thinking about after age 50. And I think what will survive me is how I have served, how I have made a difference in someone’s life, and part of the reason I created me. I don’t take a salary, I this is the thing where I want to serve because I lost friends to to midlife suicide. And I really and I had my own challenges. So to me, the good life is a life of service that is not necessarily someone else’s good life. If you are someone who’s had four kids and has lived their life in service of those four kids and caregiving, you know your your parents, your I am statement may not be I am how I serve it may be I am how I find joy. But for me, I believe deeply that my role in life, the rest of my life is to serve. And I’m excited about that because there’s joy in service.

Jonathan Fields: [00:58:31] Mhm. Thank you.

Chip Conley: [00:58:32] Yeah. Thank you.

Jonathan Fields: [00:58:35] Hey, before you leave, if you love this episode Safe bet, you’ll also love the conversation we had with another dear friend, Karen Walrond about celebrating midlife. You’ll find a link to Karen’s episode in the show notes. This episode of Good Life Project was produced by executive producers Lindsey Fox and me, Jonathan Fields. Editing help by Alejandro Ramirez. Kristoffer Carter crafted our theme music and special thanks to Shelley Adelle for her research on this episode. And of course, if you haven’t already done so, please go ahead and follow Good Life Project. in your favorite listening app. And if you found this conversation interesting or inspiring or valuable, and chances are you did. Since you’re still listening here, would you do me a personal favor? A seven-second favor and share it, maybe on social or by text or by email. Even just with one person. Just copy the link from the app you’re using and tell those you know, those you love, those you want to help navigate this thing called life a little better so we can all do it better together with more ease and more joy. Tell them to listen, then even invite them to talk about what you’ve both discovered. Because when podcasts become conversations and conversations become action, that’s how we all come alive together. Until next time, I’m Jonathan Fields, signing off for Good Life Project.