How to survive a life quake with Chip Conley

Hey everyone, Molly here. When I agreed to come on as the new host of WorkLife, I was terrified. But I was also excited to learn from our amazing guests and to share insights that could help all of you, our listeners. One of my favorite takeaways so far came from Kaya Henderson, an iconic leader who told me that leadership is really all about listening and co-creating success with your community. So, I have a request for you. Please fill out the WorkLife audience survey. It's quick, it's easy, and it's linked in the description for this week's episode. And it'll help us all make this show the best it can be. Thanks for listening to WorkLife. This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. 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Apply for Apple Card today and unlock the tools for a productive school year. Subject to credit approval. Apple Card is issued by Goldman Sachs Bank USA, Salt Lake City Branch. Terms and more at applecard.com. Someone said to me as I moved to Baja, So are you going to learn Spanish? And I said, No, I'm too old to learn a foreign language. And then they said, Are you going to learn to surf? And I said, No, I'm too old to learn to surf. And then they said to me something really amazing. They said, Ten years from now, will you still live here in Mexico? And I said, Well, I probably will part time. I love it here. And they said, Ten years from now, will you regret that you didn't learn Spanish or learn to surf now? At 56 instead of at 66, 10 years from now. And that was something that has become one of my anthem questions I ask everybody, is 10 years from now, what will you regret if you don't learn it or do it now? I'm Molly Graham, and this is WorkLife, where we untangle the messy human side of work. I've been thinking a lot lately about ambition. Not whether it's good or bad. I think ambition is wonderful. I owe a huge amount of my life and my career to it. But I've started wondering whether ambition has seasons. Looking back, I think I spent the first 20 years of my career trying to prove something. In my recent episode with Bryce Dallas Howard, you got to know a little about the family that I come from. My grandmother ran the Washington Post for almost 30 years through Watergate and the Pentagon Papers, and my dad ran it after her. As you'll hear in this conversation, I grew up in a very successful family, and I came out of it with a very specific definition of success: having a big impact in a big job. I came into the work world feeling like I had a lot to prove, to prove that I deserved to be here, to prove that I could succeed on my own. And I think that part of me was trying to prove that I could do something as important as my family history, to earn a place in my family or something. Okay, enough Molly therapy. The more I talk to people, the more I think that almost all of us show up at work with something to prove. And honestly, I think it's a good thing. It fuels us. It helped me work really hard. It pushed me to learn. It helped me discover what I was capable of. But then something... Happened that I wasn't expecting. I realized that I'd done it. I had this innate sense of confidence in my abilities at work. I'd done enough and seen enough, and I didn't think anyone could take that away from me. But almost at the same time, I realized that I didn't care about that anymore. What mattered to me so much when I was 25 simply just didn't matter to me now. Like someone had just switched out the ruler that I was using to measure success. I grew up with a stereotype of what this was supposed to look like: the midlife crisis. Leave your spouse, buy the red convertible, start over completely, blow up your whole life. But that's not what I see happening around me, and it's not what happened to me. No convertibles. Just people wrestling with whether the thing that they built in their career still fits them. And it's not happening at a specific age. I see it happening at 30 and sometimes to people at 70. After watching myself and so many people in my life struggle with changing ambition, here's what I want to know. What causes us to stop and ask whether our definition of success still fits? Does something have to break first, or can we see it coming and choose to ask before we're forced to? My guest today has spent the better part of the last 15 years thinking about this exact transition. Not just because he's lived through it himself, but because he's watched thousands of other people live through it too. Chip Conley founded Joie de Vivre Hospitality in his 20s, and he built it into one of the largest boutique hotel companies in the country. Then the recession of 2008 nearly wiped it out. Years later, after selling that company, he joined Airbnb in his 50s, where he found himself mentoring founders half his age while also becoming a beginner all over again. That experience eventually led him to found the Modern Elder Academy, where he spent the last eight years working with people in the middle of their lives who are trying to figure out what the next chapter of work and life is supposed to look like. Chip was also diagnosed with prostate cancer a number of years ago, and he's been navigating treatment ever since, which means that he has had to rethink his relationship with work and life more than once. And he's spent years watching thousands of others do the same. So I want to know what he's seen. Does something have to break before we ask these questions, or is there a way to see it coming? Well, Chip Conley, welcome to WorkLife. Oh, it's great to be with you, Molly. Thank you for inviting me. So I have a question for you to start off, which is, I feel like when I was growing up, there was like this stereotype of the midlife crisis. It was like you left your spouse and you bought a sports car and got a whole new family because your brain melted down. I actually have a friend whose dad literally did all of those things. Well, and let's be clear, and you're a man. And you're a man. Yeah, yeah. Because the way we, yeah, the way Hollywood sort of posed this, whether it was in American Beauty or The Sopranos or Mad Men or, you know, like, guess what? It was all men. They were usually around 50 years old, and it was like they went from middleescence, which is what we call midlife, the transition into midlife, to adolescence. They wanted to have all of their sort of adolescence or teenage kind of dreams met, whether it was a fast car or a fast girlfriend or— Less responsibility or more money. The truth is, I've seen very few people who fit that profile. You just described someone who it fits that, but most people don't fit that. Certainly most women don't. In fact, most men don't either. So I, this is exactly what I wanted to ask you because, like, I, you know, I'm 44, and I have a lot of friends that I see going through something, and I feel like more what they're doing is stopping to ask questions and sort of wondering about, like, the role that work plays in their lives and also whether the thing they've spent the last, you know, 20 years building is still what they actually want. I'm just, and I want to hear, like, is that the pattern that you see as well? And do you think, like, the midlife crisis has changed, or is it just that we're seeing it sort of in a different light? Well, you know, let's be clear that the origin story of the midlife crisis is 60 years old, and it came from a very unknown Canadian psychologist who studied a few men, and then it stuck, and it became sort of a meme. Having said that, there's not a ton that shows that there is a widespread midlife crisis. What there is, and the U-curve of happiness research has shown this, is there is a long, slow decline in life satisfaction, although today, these days, that life satisfaction for young adults is very low. But historically, there's been this long, slow decline of life satisfaction that bottoms out around 45 to 50. And there's a lot of reasons for that. It's not a crisis. It's more a stuckness. The aperture of your life is closing as opposed to opening. And that's partly because if you're a sandwich generation folk, taking care of parents while you're also taking care of kids, that takes a lot of time. It's sort of maximum time for making money potentially in your career. And so you can feel disappointed if that's not what's happening. There's a lot of expenses during this era, especially if you have kids. There's physically, I mean, women are starting to go through perimenopause or menopause, and men have this thing called andropause they don't even know about, but it's a thing. There is a hormonal change in men. So what's going on for a lot of people is they feel stuck and maybe even a little disillusioned. My friend Brené Brown calls it the midlife unraveling. And when she first said that to me, she said, Chip, you've got this Modern Elder Academy, MEA. Like, are you going to talk about the midlife unraveling? And I was like, Wow, that sounds terrible. Like you're losing your mind. She said, Well, if you look in the dictionary under the word unravel, it means something so tightly wound you can't get it undone. And I think for a lot of people, that's how they feel their life is around 45 to 50, is they feel like it is so tightly wound. It's a precision machine, and their job is to optimize. And they may be reading from a script that was not their success script, but their parents' success script. And that's when sometimes people go off the rails because they realize this isn't who I am. So will you just tell me your version of this story? Like, when did this happen for you? Yeah, you know, so I started a boutique hotel company called Joie de Vivre in San Francisco back when I was 26 years old, and it grew into a big company. During the dot-com bust, it was a struggle, but we actually did fine. But it was during the Great Recession that everything sort of came to roost. This is 2008 when you say Great Recession? Yeah, 2008 to 2010. We had 52 boutique hotels. The Great Recession was quite punishing, but it was more than that. I had a long-term relationship that was meant to end, but I was just holding on to it like a life preserver. I had an African American foster son who was an adult who was going to prison wrongfully, and I was trying to get him out on appeal. I lost five male friends to suicide, all of them 42 to 52, all of them men, between 2008 and 2010. And then I had an NDE. I had a near-death experience where I had an allergic reaction to an antibiotic, and I died, you know, and I went to the other side, and I had all the experience of what it's like to be on the other side and then come back. And all that happened around age 47, which is the low point of the U-curve of happiness. And I think more than anything, what I felt was this deep sense that every day is a bonus, and if I am not feeling fully aligned and in love with how I'm curating my life, I need to take the hard steps to making some changes. And that's really what I did over the next two years after the flatline experience. I ultimately sold the company at the bottom of the Great Recession, which was not the right timing, but it was perfect timing for me after 24 years. I was burnt out. I got my son out of San Quentin, but that took two and a half years. I ended the relationship that needed to end. And I said to myself, I want to have what's called a midlife atrium. There's a woman named Mary Catherine Bateson. She was Margaret Mead's daughter. She was a Harvard professor, and she says we've gotten longevity wrong. We think that with the extra longevity we have as a society, we are adding an extra bedroom or two to the backyard of life, as if we're just going to be old longer. And what she said, what Mary Catherine Bateson said is that, no, what we really need is a midlife atrium. We need a time when people can actually take a step back, ask bigger questions, maybe take a little bit of a sabbatical, and look at how do you want to curate the second half of your life. So for me, I was 50 at the time that the company sold, and I'd gotten through the bad times. And, you know, 18 to 50, you know, adulthood for me had been 32 years long, from 18 to 50. And based upon the math, I was probably going to live till 82. So I was halfway through adult life. Most of us don't think that way at age 50. So how do I want to curate the second half of my life? So I spent two years in this midlife atrium. You know, what we love about an atrium, it's space and light and light and air and the opportunity to explore things. And so I got curious about three things. I went deep learning about these three things, and it took me on a beautiful journey of realizing, oh my gosh, I have spent the last few years closing my aperture because I was so busy. I didn't have time for curiosity. I didn't have time to wonder about things or explore something that I was really interested in and maybe I neglected from childhood that I wanted to explore again. And ultimately, I got a call at age 52 from the founders of Airbnb. Airbnb, at that time, 14 years ago, a tiny little tech company that most people had never heard of, to come in and be their modern elder, someone as curious as they are wise, their in-house mentor. House mentor. A lot of what you're saying really resonates with me, and I did not almost die, but there was a lot of events that happened for you that kind of coalesced into forcing you to take a step back and ask whether you were still doing—you were living the life you wanted to live. I'm curious, like, before you got to the atrium, like, can you just talk about what that phase felt like? Because I think I do see this in a lot of friends where, like, you know, cancer diagnoses and things like that that just really do force you to face the fact that you only have one life and you don't always know how long it's going to be. But I'm curious, like, what it felt like for you, but also do you think something like that has to happen to force this? No, I don't think it does. But I think for me, what I was going through was I was going through—when you start getting what Bruce Feiler, the author, calls a lifequake, where you're having multiple transitions at once, it can feel like a pileup, like a crash on a freeway. You can sort of feel like you're doomed and you're doing something wrong. There's a lot of emotions attached to this where you can feel like something—you feel stupid, you feel embarrassed, maybe even ashamed. And so for me, I think what I felt was stuck more than anything. I felt I'd started this company, I'd created something that was a bit of a Frankenstein that, you know, I was the CEO and the founder, and it sort of revolved around me, even though we had 3,500 employees. And you and I both have a common friend, Vanda, and my friend Vanda is a coach, and she helped me through this time. She helped me to see that— I had these identities that I was holding on to, like life rafts, and that I could actually let go of these identities and still be me underneath the business card and the title and the VIP status. Yeah. And that's a hard one for a lot of people, especially in midlife. Who are you without your marriage? Who are you without being a parent? Who are you without being the vice president of development? Who are you without being a Christian? Who are you without being a variety of things? There's a lot of labels we have, and I'm not saying labels are bad, but I am saying that sometimes a label is too small to contain who you are becoming. That really reflects my own experience, including Vanda dramatically helping me unstick myself. And it is interesting, like I've sort of been wondering if it's about rewriting a definition of success, because like I think for me, like I showed up in my career with a lot to prove, and, you know, I'm very grateful for that ambition, and I think I spent, you know, 15 or 20 years really crushing in order to, like, make a space for myself. And I think you talk about it as, like, having all these identities, and I think, like, you do have this phase where you're, like, really having to build an identity outside of your family, and that's good. But then there's a moment, or at least there was a moment for me when it really, and it sounds like a little bit the same for you, where I just really hit a wall. Like I built this beautiful cage that everybody else looks at and is like, Wow, that's such a beautiful cage, and I'm like, It's a cage, you know? So let's explore this for a second, Molly. We're going to put the attention on you for a minute. So did you come from a family that gave you a bit of a success script about what defines success? Definitely. I come from a very successful family, and I had a lot to prove, or I felt like I needed to prove, like, that I could be successful separate from them, you know? Okay. So even though, you know... There's a term that I've helped to coin, which is successism. And successism is when there's a dominant ethos in either the community or the culture or in your family that you respond or react to. You might fall in line and say, I'm going to be a better version of that. You might actually say, like, I'm going to be the opposite of that. But part of your life, especially your early adulthood, is in reaction to it. And for me, as well as you, I was the firstborn of two firstborn parents who both met at Stanford, and I went to Stanford, and I was Stephen Townsend Conley Jr., chip off the old block, and my dad wanted me to be a better version of him. And so I had to go through a process at age 22 when I came out as a gay man, and that was really hard for my dad. But it might have been the best thing I ever did in my career. And the reason I say that is because, I mean, yeah, in 1983, coming out as a gay man in the midst of the AIDS hysteria, living in New York and San Francisco, like, okay, this is maybe not good for my health, maybe not good for my career. But what it allowed me to do was break some of the success script. It allowed me to start being more independent. And so in some ways, what I think is great about millennials is a lot of millennials have asked some of those bigger, deeper questions earlier in their adulthood, such that they may have actually taken a step in a direction further away from what I might have done in my game of life board game approach, which is like, remember the Game of Life, like an American propaganda tool, where like, okay, there's one path of success in life. And when you can finally see it, like the Matrix from the outside and say, I don't want to be part of that anymore, it allows you to make some changes. What do you think are the most common sort of success scripts that people start with? Like, what are the patterns you see? The comparison. Comparison is the thief of joy, and how we— Do our best to fit in and try to be a version of ourselves that's better than the person next door. I think that's a tough one. Or better than your sister or your brother, your sibling, who you're being compared to all the time. I think that's one thing. I think this idea, the arrival fallacy, something that has been written a lot about. The arrival fallacy is this premise that if you get on what's called the hedonic treadmill and you run fast on that treadmill, once you get and you attain what you have been looking for, the pursuit of happiness, that pursuit of that job, the pursuit of being the, you know, the host of the WorkLife podcast, once you have that, it's in the palm of your hand and it doesn't look quite as alluring as it did when it was out there on the horizon. So there's this weird sense that people have that when you hit the arrival, you'll be happier, when in fact, when you hit the arrival, there's some new shiny object that gets your attention, if that's the way your mind is working. Or like, is it like all this misery right now is okay because once I get there, I'll be happy? Is that the kind of arrival? There's certainly that as well. And some of that's just built into how we live our lives. I mean, you know, kids bring long-term meaning but short-term unhappiness. And certain career paths can do the same. So, yeah, I think for many people, there's this deep sense that It's one of two things. Around midlife, you're either saying, Is that all there is? which is the real arrival fallacy perspective, or you're saying, I'm disappointed, because, you know, disappointment equals expectations minus reality, and I had expectations here and reality is here. And social scientists have shown something that's really interesting. What's happening in midlife, often right in the core of midlife, around 45 to 50 or early 50s, is we start to actually ratchet down our expectations about things, which can sound, for those of us who have built our lives and our successes on expect a lot out of yourself, that can sound terrible. But actually, what happens is that we reduce our expectations, and in so doing, our reality starts to improve. And if disappointment equals expectations minus reality and expectations are coming down and reality continues to improve, you do get to a place where you have delight and not disappointment because your reality is better than the expectations. So that's an interesting thing. And whether you feel that way about your marriage or you feel that way about how much money you have in the bank or how you feel about how successful your kids are, it's a really important thing. This episode is sponsored by Framer. When I think about what makes a great website, it's two things: careful design and a fast turnaround. Usually, you only get one. Framer's built so you don't have to. Framer is a complete website platform, not just a builder, so teams can launch and keep improving their sites in minutes instead of days. What sets their platform apart is that AI agents work directly inside the canvas, the same place where the real site is designed, managed, and published. 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So instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. In fact, LinkedIn found that its users are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com/worklife. Terms and conditions apply. This episode is brought to you by Quince. Fall has a way of slowing us down in the mornings. Crisper air, hot cups of coffee, and a coziness you don't want to rush. But when it's time to get moving, I lean on pieces that make getting dressed easy so I can get out the door and still look great. That's what I like about Quince. They make quality basics designed to work across your wardrobe, everything from cashmere sweaters all the way to breathable activewear. 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And I will say, like, for me, for sure, turning 40—interestingly, like, the math, you did it at 50, I did it at 40—where I was like, I hope I'm healthy and well in my 80s, and that means I'm halfway through my life, you know? And I was like, that can be a stark moment, because I think there's early phase, I feel like I have infinite time to do everything I want to do, and then you hit something and you're like, oh, not as much time. Is there work that people can do earlier that makes this not a crisis, that makes you not have to almost die or whatever? Yeah, I mean, first of all, one of the things that we teach at MEA is transitional intelligence, TQ. And to know that, as Dan Gilbert from Harvard said, we are going to be constantly going through transitions in life. And so once you understand that any transition has really three stages to it—the ending, the messy middle, and the beginning—it allows you to see where you are in each of those and what's the coping mechanism that will help you. So when you're ending something, it helps to ritualize it. It helps to sort of say, like, okay, this is an era of my life that I'm ready to let go of. How do you either personally or collectively ritualize that? The messy middle, you need social support, and you also need to find your through line, because when you're in the messy middle of something like the chrysalis stage between caterpillar and butterfly, things are liquefying. I mean, it's sort of a scary time because you're in a moment in which the ground doesn't feel stable. And so the social support and being able to see the through line—the through line means you can see the other side of this. You can see on the other side of this, if you're going through a divorce, for example, that that's painful and it doesn't feel good at all. But on the other side of it, you're probably going to be wearing a better pair of glasses as you consider your next mate and who you're going to date. Yeah, okay, that makes sense. When it comes to the career path, same thing. Your painful life lessons are the raw material for our future wisdom. But one of the things that people really need to actually lean into in midlife is what have you learned, and how is it going to serve you and the people around you in the future? And we can come back to that. That's so, in that messy middle, understanding what you have to offer in the world. And then the third stage is the new beginning. And Carol Dweck's work at Stanford about mindset is really important here. Having a growth mindset will allow you to be a beginner at something and be bad at it. And that's one of the challenges for a lot of people as they get into midlife, is they're used to being competent, and they don't like being bad at something. So one of my top things that I suggest to people is go learn something new that you can be bad at. Become a dabbler at something. And if you hate doing it, don't do it. But if you like doing it and you're not very good at it, that is beautiful, because curiosity and openness to new experiences are both positively correlated with living a longer, healthier, happier life. So you don't have to go out and fail at something. You don't have to have a tragedy. But you do have to say, I'm going to try some noble experiments. I'm going to learn how to surf. One of the things that happened to me at 56 is I moved to Baja in Mexico part-time. In Mexico, part-time. I was still working for Airbnb part-time. I had been full-time, and now I was part-time, and I hadn't started yet the Modern Elder Academy, MEA, with our first campus being in Baja. And someone said to me as I moved to Baja, So, are you going to learn Spanish? And I said, No, I'm too old to learn a foreign language. And then they said, Are you going to learn to surf? And I said, No, I'm too old to learn to surf. And then they said to me something really amazing. They said, Ten years from now, will you still live here in Mexico? And I said, Well, I probably will part-time. I love it here. And they said, Ten years from now, will you regret that you didn't learn Spanish or learn to surf now at 56 instead of at 66, ten years from now? And that was something that has become one of my anthem questions I ask everybody, is ten years from now, what will you regret if you don't learn it or do it now? I love that, by the way. What I heard you say was, when you realize that the success narrative has ended or stopped serving you, you need to, like, have a funeral for it, basically. Acknowledge the end, get comfortable with the middle, the liquefying phase, and then challenge yourself a little bit, like try to get comfortable being uncomfortable. Talk just about the funeral thing, because, like, when I was in that phase, I just felt like it felt super dark. It felt—I felt—I didn't know why, though. And it really took me like a year to figure out that I just needed to break a bunch of glass in order to find this new path. I don't even know if it took me a year. It might have taken me like eight years to figure. So help me shorten that. How do I shorten it? Yeah. Learning TQ, transitional intelligence, allows you to move through this process more rapidly. Bruce Feiler, in his book Life Is in the Transitions, and he's a faculty member at MEA, he says that the average transition takes three to five years. That's a long time. That resonates. Yeah, it takes a long time. So the thing to consider, there's a woman who came to MEA in the early days named Mariana, and she had a branding and design firm, and— She was really good at what she did. And therefore, all these different clients in the Bay Area, especially tech firms, would come to her and say, Help us with branding. Help us with graphic design. And so she had to build a company, and she built a big company. The problem with those in the Bay Area, and you know this, Molly, is that it's a feast or famine culture there. So she loved the work. She hated being an employer because in the bad times, she had to lay people off. She came to MEA and she said, I don't want to do this anymore. I'm done with this. But I have all these employees. I have all these clients. I feel such a responsibility to them. I feel the momentum of this thing I've built. I have the identity attached to that. By the end of a few days, she came to the conclusion, I'm going to invite all of my current employees and current clients, my former employees, my former clients, my friends and my family to a cemetery, and we're going to have a wake for this company because I'm going to announce that in the next six months, instead of having 20 employees and, you know, 40 clients, I'm going to move this company down to just three people: me, an apprentice who I can teach this business to, and an executive assistant. And in the good times, we're never going to have more than that. We'll just charge a lot more. And in the bad times, I won't have to worry about the employer piece. And the fact that she did it in a public kind of ritual way allowed her to feel the support that she needed. Let's take a step back here for a moment. Rites of passage are something we've had since the start of mankind, humankind. Generally speaking, rites of passage happen when you're going through a major transition. And a lot of them are, you know, early in life. A lot of them are adolescent or early adulthood, whether it's, you know, puberty or it's getting married or having a baby. With the additional longevity we have, we have not created midlife rites of passage or rituals. Turning 50 should be a big deal in our culture. We should have something around that. Now, in Asian cultures, turning 60 is like they call it the second childhood, and they have a whole thing about it. But in the U.S. culture, we really have nothing. You don't have to do what Mariana did and take everybody to a cemetery. You literally could sit down with your best friend and say, you know, I'm getting divorced. I want to end my sense of codependency with my husband, and I want to move into this messy middle phase, but here's the things I need to let go of. And you write down a bunch of things I need to let go of, and then you and your friend are there and you throw it in the fire. It could be something that simple. You could do this with teams as well, when a team knows there's a transition necessary. So, yeah, I mean, rituals are a part of our humanity. Yeah, I feel like I wish I'd had that because I just sort of shuffled through it for a very long time. Out of curiosity, like, we talked about definitions of success and then this idea of sort of like needing to shed it. What are—is there something you wish more 20-year-olds or 30-year-olds knew, like a different definition of success or a set of questions that you wish folks that were earlier in their lives asked in order to, like, lessen some of this thrash? The question I like to ask people often early in their careers is like, What would you like to be world-class at? And it doesn't even have to be your career. It could be being an amateur photographer. But what is it that would be meaningful to you about being world class, and why? What is it about that particular topic? And then the why becomes really important. And the why has to be asked with a certain amount of empathy because, like, a why that sounds like it's questioning, you know, what you've answered is not good. But this idea of helping a person get clear on why that thing matters to them, that's important because that's breaking out of maybe the success script that they have been handed. So I think that's a really important question. So is the point there asking what makes you happy in addition to what sort of somebody else handed you as a definition of success? Is that sort of your point? Yeah, what makes you happy, but also what comes naturally. You know, Mahali Csikszentmihalyi was one of my mentors, and he popularized the idea of flow. When you're in a state of flow, you're doing something that where challenge and skill are in a perfect match. You are doing something challenging, but you're building skill while you're doing it, and you're going up the stair steps of challenge, skill, challenge, skill. That is ideal, is to find something that puts you into a state of flow. How do you know you're in a state of flow? When you're in a state of flow, you typically lose track of time. You feel a sense of joy in what you're doing. You feel very competent, confident, and curious. The first two are obvious, competent and confident, but someone could also be full of ego and lack of humility. But the curious is really important too, because it's something that actually gives you a sense of flow, gives you a sense of you want to learn more, you want to understand it more, and that requires a certain humility and a beginner's mind, like, okay, I want to learn more. I want to get better at this. So I think finding something that puts you in a state of flow is one of the more important things a person could try to learn early in their career. I love that. A lot of times I feel like you see these, and I post them on the internet too, where it's like, Here's what I wish I'd known at 20, you know? And everybody comments and is sort of like, This is such great advice. And then one person, you know, will always say, This is such great advice, and no one that's 20 is going to listen to it, you know what I mean? Because the truth, and I think, you know, this is true as we transition generations in general. Like, I did this when I was 20, where I was like, Shut up, older person. Like, I'm not going to be like you. Do you believe that wisdom is actually transferable? Like, can we actually gift some of this to folks that are younger than us? And, or is this proving phase or sort of, you know, that early phase just really, like, necessary and important for people to then become who they need to be later in life? Like, I'm just curious how you think about that. Well, let me define wisdom in the way I define it to start with. It's metabolized experience, life lessons, mindfully shared for the common good. One of my lessons at Airbnb was that there were certain parts of my life I had wisdom, but I thought of it as common sense, and I didn't think it was really valuable because I thought, like, everybody knew that. But at 20 years old, I didn't know that. So what I started to do, especially initially with Brian Chesky, the CEO, and who I was mentoring, but I was also learning from him, I called myself a mentern, a mentor and an intern at the same time. I learned DQ from him, digital intelligence, because I was a bit of a Luddite at age 52 when I joined the company, and the average age in the company was 26. And he learned EQ. So I learned EQ from him, he learned EQ from me, and we were both better off for it as a result. So what does that mean? It means, like, there are things that we are supposed to learn from younger people. And when we are older, leaning in to learn from younger people, it is going to create a symbiotic relationship. And that's why that second piece, metabolize experience, mindfully shared. If you remember the meme a few years ago of OK Boomer, and it was a woman holding her hand out, you know, palm forward, like, stay away. And the origin story of that, from what I've heard, is that a younger woman in a workplace was just tired of this older guy coming to her and saying, telling her, This is how the world works, because it's how his world works. His, you know, word stories were his wisdom. But he didn't present it in a way where there was context or symbiotic relationship. He presented it as if, You're supposed to sit at my feet and I'm supposed to tell you stories. And she was tired of that. So this mindfully shared is really important. So yes, 20-year-olds don't want to listen to a 50-year-old if you feel like their parent. And one of the things I had to learn at Airbnb was how not to become the parent, which meant I had to be curious. You know, I had to be as curious as I was wise, as they called me, the modern elder. And what that meant was I needed to ask a lot of questions. And that was a really important thing for me. And I've learned that from Vanda, this idea of appreciative inquiry. Appreciative inquiry is how do you ask questions that are catalytic? Knowledge speaks and wisdom listens. So wisdom listens and then ask great questions. And so I think the intergenerational collaboration we need in the workplace today, with five generations in the workplace for the first time, and by the end of two years from now, I think 2028, the U.S. Department of Labor says that the majority of Americans will have a younger boss. We have never seen this before. Take that in. The majority of Americans will have a boss that's younger than them. Now, in my case, not 21 years younger like I had with Brian, but we're going to have to get used to the idea that a new generational compact is supposed to happen. We are supposed to learn from each other, both the knowledge and the wisdom, but the wisdom is even more important. Can I give you a little hack, a wisdom hack? Yes, please. So my wisdom hack is something I've been doing since age 28, and then I modified it for the leadership teams that I've run at Joie de Vivre, Airbnb, and now MEA. The leadership hack is this: at age 28, I was a clueless CEO, and I felt like I wasn't doing a very good job of understanding what I was learning. So I took a journal off the bookshelf, and I wrote on the cover of it my wisdom book, and I started the following practice. Every weekend, I sit down for 20 minutes, and I ask myself, what were my biggest lessons this week? And they were usually painful. And how will they serve me in the future? So I did that practice. I've been doing it now for, what, 38 years. The thing I do that's the hack for a leadership team is the following. With the leadership team, we sit down once a quarter, and we ask ourselves, What was our biggest lesson of the quarter? And then whoever's the most senior person in the group will start and say, Here's my biggest lesson. It's usually something they're a little embarrassed by or something that didn't go well. Here was the lesson. Here's what I learned from it, and here's how it's going to serve me in the future. Wisdom is not taught, it's shared. And the fact that the CEO of the company or the VP of marketing or the, you know, the CFO just said a lesson they learned, I can take their lesson in and learn from it. But we then also end the meeting after each of the leadership team members talks about that. Again, we do this quarterly. We end the meeting with the following. We say, What was our biggest team lesson of the quarter, and what can we learn from that? So you better have a slightly functional team to be able to do this. Otherwise, people are going to be pointing fingers and saying, My biggest lesson of the quarter is the CFO is a jerk, and that doesn't help anybody. But I have found that we are entering an era where knowledge management practices, which were such a big part of our era of the last 60 years, knowledge management practices don't mean as much as they used to because of AI. But what will matter a lot is wisdom management practices. How do we develop the wisdom of a team in such a way that we learn from each other? This episode is sponsored by Skylight. If you have kids in school, you know how hectic the transition from summer vacation to the classroom can be. One week the whole family is traveling together, and the next, everyone's on a completely different schedule. What's made this time of year a lot easier for us is the Skylight Calendar. It's an all-in-one smart calendar that syncs seamlessly with Google Calendar, Apple Calendar, Outlook, and more, pulling everything into one shared view. In all honesty, our household is kind of chaotic, and the only way I stay sane is through a shared calendar that shows us everything, which is exactly what we get with Skylight. And you can try it risk-free. If you're not 100% satisfied within the first four months, just send it back for a full refund. Families are better when they're working together. Right now, Skylight is offering our listeners $30 off their 15-inch calendars by going to myskylight.com/worklife. Go to myskylight.com/worklife for $30 off your 15-inch calendar. That is M-Y-S-K-Y-L-I-G-H-T dot com slash worklife. Today's episode of WorkLife with Molly Graham is brought to you by Olympic Hospitality. The Olympic Games are coming to Los Angeles in 2028. This is a once-in-a-generation event that you will not want to miss. It's more than a ticket. 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Terms apply. See capitalone.com slash bank. Capital One, N.A., member FDIC. Man, Chip, I could talk to you for hours. So, there's this moment—I mean, you talked about the transitional intelligence, and it's, you know, the funeral, the middle phase, and then getting curious about things. One thing that was really hard for me, maybe still is, was figuring out what to focus on next, like shedding this definition of success I kind of got to slowly. But how do I think about what is good next and not let the sort of, like, old monsters creep in was really challenging. Like, how do you help people with that, and what did that look like for you? Yeah, I wrote a blog post entitled Leaving Before Knowing. And in that blog post, I talked about mindful decoupling, not conscious uncoupling, that's a different thing, but mindful decoupling. How do you decouple the idea that you know something has lived out its life and it's time for you to move on? How do you let that go and be open to moving on before knowing what is the next thing? And again, that's that messy middle, that chrysalis. And I think the key is for people to, again, leaning into both social support, but also leaning into the curiosity. When I joined Airbnb, I almost quit after three weeks because I felt like such an idiot. I didn't understand technology. I didn't understand millennial travel habits. I was the only boomer in the company. And my dad asked me a really provocative question, Chip, how can you turn your fear into curiosity? And it was in that moment that I just said, I can't be the smartest person in the room at times, but I can be the most curious. And it is that curiosity. Curiosity helps you to move beyond judgment and self-criticism. And so curiosity is an exceptionally valuable quality for someone to have in their life. The problem is that we are very curious when we're young, and yet we sort of get curiosity bred out of us with standardized testing and then with really full and busy lives. You know, you don't want to be curious on a treadmill because you're sort of looking all over and you might fall off the treadmill. So you've got to be focused. And being focused is sort of the opposite of curiosity. And when we have like 25-minute long meetings in a company and that's all you do, there's no space for curiosity. So the question is, how do we curate curiosity in our lives, in our leadership teams, in our company, in a way that opens up ideas, epiphanies that wouldn't have come otherwise? It's not just a matter of having time. There's, you know, you better have good facilitators, and there better be some provocative questions, et cetera. But curiosity requires a certain amount of spaciousness. I've said to people, talented people deserve empty space. And what I mean by that is even if you don't know what the next thing is, if you have talent and you have curiosity, you are good soil. Something is going to grow out of that good soil. If you don't have talent and if you don't have curiosity, that might be barren soil. But if you have talent and you have curiosity, trust, have faith that you will be good soil and something will grow out of that. When I sold my company at age 50 and got curious and had my midlife atrium, I didn't know what was next. I didn't know that Airbnb was going to come knocking on my door two years later. I didn't know I was going to start a festival company called Fest 300 and go to 36 festivals in 16 countries around the world, partly because I was the first board member of Burning Man and I was like, I'm curious about festivals of all kinds. So finding room for curiosity is such an important part of it because not only does it give you space to have something grow out of the soil, but curiosity is the opposite of being self-critical. It also sounds like what you're saying, which actually really does resonate with my experience, is trusting your curiosity. That if you are genuinely interested in something, that that's energy that you should follow, which actually is basically what I did when I felt completely lost, which was just like, let's go figure out what sounds like fun, you know, and do more of that. Well. And there may, while there's not a lot of research on this yet, but curiosity may have some relationship with intuition. There's been some work on this, and then also intuition and wisdom. So there's an element of curiosity as sort of a doorway. That's the way I like to think of it. It's a doorway of possibilities. It opens up possibilities. And if you believe in that, then, you know, you have to have some faith that curiosity is going to help you create the conditions for something to come into your life. I love that. And yeah, that really resonates. Okay, I just want to ask you one question about money, because I think it's really easy to listen to conversations like this and be like, yeah, yeah, yeah. You know, like, sure, I would love to have an atrium. I would love to leave without knowing, but I feel trapped, right? I feel like I have to stay in this job or stay in this career path because, you know, to your point about the highest earning years, like, I need to make this money for my family. Like, I'm sure you see this with MEA. Like, how do you talk to people about sort of the financial side of this, since that is such a huge part of work? Well, I think the first thing is you better have your responsibilities, obligations, and financial things in order. I don't want you to go off and do something crazy. So being, you know, responsible is really important, and it may require some patience. It may mean you are not going to get paid to do the thing that you find might be a calling for you until five years from now. So that doesn't mean you can't start doing it. You could start doing it on the side, but not for money. Or you do do it for money, but it's just a part-time thing. You know, as we get older, ideally we create a purpose portfolio. We're not defined by a singular job or a singular identity as a parent, but we actually take this sort of this pie chart and with these bubbles, and instead of having one or two bubbles in the purpose bubble dominate, you can have a lot of different bubbles. And so, yes, you may have to be responsible and stay in the job you're in right now, or find a new job that, you know, is going to be as good or better financially that you're going to enjoy more. And that's going to dissuade you from going to do the thing you would love doing. That's part of being an adult. Having said that, it doesn't mean you can't start to tap into the passion. There's a woman who came to MEA who was a litigator. She hated litigating. She wanted to work 10 more years. She was 60 years old. She wanted to work 10 more years till 70. And you can understand why she might hate litigating. She started tapping into childhood dreams of wanting to be a baker. She used to bake pies with her grandmother. And so she went to pastry chef school. And then she started, like, having friends over for meals and for pastry parties. And, you know, it took her a while to get there because she had some financial responsibilities that she had to focus on. But at some point, she became a bakery entrepreneur. But it didn't happen overnight. She had to do the work and she had to take the incremental steps. Herminia Ibarra has a great book called Working Identity. She's also a faculty member at MEA. She's based in Europe. And one of the things she talks about in Working Identity is the idea of take, experiment, try some steps, do some small steps that allow you to see how would this be if this became my full-time job. And so I highly recommend that. I love that. I also, I really like the words purpose portfolio. I've never heard that before. So I want to ask you one last question, and I apologize for ending on a sort of a dark note, but you've mentioned your near-death experience, and I know you're also on a cancer journey. And we talked about this idea of, like— Maybe like transitions you choose and then transitions that choose you. And I think there's lots that, you know, I've watched friends learn from having to face down mortality. But, you know, folks that haven't had to face that, I'm curious, like, you know, what would you tell someone that you wish everyone knew, having had to face this down yourself in terms of, like, the relationship of life and work and what all of that has taught you? Well, it's funny. I, yeah, I've had—well, we've known I've had prostate cancer for over eight years, which is serious, means it's spread through my lymph system. And we've known that actually for three and a half years. And so I've had so much, so many treatments, so much stuff going on. But I think the thing that I feel that is an interesting dichotomy is one of the things I feel is this sense of holy urgency. Holy urgency. The sense like, I don't know how many years I have left. There was a point at which two years ago my doctor said, my oncologist said, I think you have a 22% chance of living another 10 years. That's not very good. The next day he came back and says, like, I put your data into a different model and it's 80%. It's like, oh. Well, uncertainty. One of the things you get used to is uncertainty. And you get used to the idea that every day is a bonus. How are you experiencing gratitude? You know, Laura Carstensen at Stanford Center on Longevity has shown that when people have a perceived shorter amount of time left in their life, they tend to focus not on the future or the past, but on the present moment. And focusing on the present moment, they become happier. So there's, you know, having a terminal or, you know, an illness that is chronic is not something you want, but it does have some upside. The thing, the dichotomy I have is the holy urgency with this message I got when I had my NDE at age 47, which is slow down. Slow down. And that's what the birds were singing to me and saying to me. I could understand bird talk because when you're in that liminal stage between life and death, all kinds of weird stuff is happening. And so my life today is this strange alchemy of learning how to just slow down and appreciate what matters most, with this deep sense of calling and holy urgency that I don't want to regret that I didn't put my full heart and passion into the things that matter most to me. So that's the mixture. That is a very beautiful mixture. Complicated one, too, I think. I love that. Chip, thank you so much for this. This was so great. Thank you, Molly. Okay, that was really fun. I've really been looking forward to meeting Chip just because I've heard so many wonderful things about him and about Modern Elder Academy. I got so many things out of that conversation. What I really wanted to understand was, is the midlife crisis a thing that everyone just has to go through? You know, is there a way not to avoid it, but to sort of like do some work earlier so that you don't have these dark, dark moments in the middle of your life? And then also, thing two was, does it have to be a crisis? Like, does it have to come, you know, like a thunderclap or a terrible event or something like that? And I guess what I took away was everyone's going to go through it. There is something about time in your life getting shorter and more precious. Biologically, things are happening in your 40s and 50s. All of that, you know, what I heard from him is everyone is going to go through something in this phase of life. But— I did hear that it doesn't have to be a crisis. That there is work you can do and tools that you can take on earlier that will help it be less of a wall or a thunderclap or a dark, dark tunnel. And I wish I'd had those, for sure. There were so many interesting tools and things that he mentioned, but I will tell you the one thing that I am really thinking about, because I've never been able to explain it until he said this, was the idea of curiosity as a compass that's going to lead you out of the sort of messy middle phase or the darkness. Like, to me, that is actually what I did to get to the other side, but I could not have explained it before this conversation because it was a long, dark road to sort of shed my ego and this previous definition of success that was really powerful, and really to learn to ask, like, what is it that I want? What feels like the most valuable use of my time now? But the way that I did that, and it did not feel energetic for a big part of it, was just asking, what am I curious about? What is it that is naturally drawing my energy? What do I wake up thinking about? What, when I'm doing it, feels good? And, you know, Chip had a lot of different questions that he asked that all, you know, focus around that same set of questions. But that is how a lot of the community work that I do now started. It was stuff that I was curious about, and I found that the more that I did it, the more I wanted to do it. And there was a lot of experiments, by the way, that I tried that did not have that property. Like, I was, you know, consulting for companies and things like that, and it was draining to me. And that ended up really telling me where I should invest my time and ultimately built me a compass out of curiosity, apparently, which I, again, would not have been able to explain before this conversation. So I love that. And I think, you know, cultivating your curiosity and being willing to be uncomfortable in that curiosity was such a powerful message from Chip. So I hope you all enjoyed this conversation as much as I did, and I'll talk to you next week. Work life is a. Work Life is a production of TED and Pushkin Industries. This episode was produced by Isaac Carter and Leah Rose. Bandband Shang is our story editor. Mixing by Hansdale She. TED's executive producer is Daniela Ballarezo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Highlash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my Substack, Lessons. I'm Molly Graham. Thanks for listening. With no fees or minimums on checking accounts, it's no wonder the Capital One Bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends. It's pretty much all he talks about. In a good way. What's in your wallet? Terms apply. See capitalone.com slash bank. Capital One, N.A., member FDIC. Hey everyone, it's Chris Guillebeau here, host of the Side Hustle School podcast. This episode is powered by AT&T Business. In my early days, I did some of my best work in parked cars or coffee shops. But when I landed my first big contract, I realized I couldn't bet my future on a public connection that cuts out if someone turns on a blender. 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