Tami Simon: Hello, friends. My name’s Tami Simon, and I’m the founder of Sounds True. And I want to welcome you to the Sounds True podcast, Insights at the Edge.
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In this episode of Insights at the Edge, my guest is someone that I consider a soul friend, a hugely accomplished human being, Chip Conley. Let me tell you a little bit about Chip. Chip has disrupted the hospitality business, not once, but twice as the founder of Joie de Vivre Hospitality, the second-largest operator of boutique hotels in the United States, and then as Airbnb’s head of global hospitality and strategy where he was named the “modern elder” on the staff, someone equally wise as curious. In January of 2018, Chip cofounded the Modern Elder Academy, which is the world’s first midlife wisdom school. They have one of their retreat centers in Baja California and then a new center opening this year in Santa Fe, New Mexico. Chip is a New York Times bestselling author of seven books and a new book. It’s called Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. Chip, welcome.
Chip Conley: Oh, Tami, thank you. It’s great to be here. I’m realizing that I’m actually staring out a window here in San Francisco where it’s getting dark now, so my image may just get darker over the course of the next hour, but other than that, I’m feeling relatively light, even though I’m going through a lot of different changes in my life right now.
TS: We’re going to talk about that. We’re going to talk about your new book, Learning to Love Midlife, and this capacity that you have. And ever since I’ve known you, Chip, I’ve seen this in you. It’s almost like this power of regeneration, power of renewal. You go through some kind of, I’ll just call it in plain English, total system meltdown, or somebody might say—
CC: Clusterfuck.
TS: You could call it that, something like that, like, “Oh my god, huge destruction of your life-form as it was,” and then—this is the miracle part—something new and brilliant and fabulous and unbelievable and generative and helpful comes forward. And I want to learn more about what you’ve come to know about that pattern in your life and this capacity of regeneration.
CC: It’s interesting you say that, because my very first hotel as a boutique hotelier, I called this pay-by-the-hour motel that I was turning into a rock-and-roll hotel that now you pay by the night, it was called The Phoenix, and it’s a well-known rock-and-roll hotel here in San Francisco, and the Phoenix rises from its own ashes. And I’m a Scorpio, and Scorpio has sort of a life-death kind of thing going on. So it’s woven certainly into my history in this lifetime, but I have a feeling it’s coming from past lives, too, the fact that I have a tendency to have to manifest a transformation in my life, and often in a transformation you have to go through something dying, so yes.
TS: I want to talk about—we’ll just call it the “Phoenix phenomenon”—and I want to talk about it because I think a lot of times when we’re in the death throes, even though we’ve heard about it, we think, “Well, that renewal, that rising again of the Phoenix that might happen for somebody else, but at this moment, I don’t think it’s going to happen for me. I’m out. It’s not happening for me.” And I want to help our listeners and I want to learn more about how we activate that renewal capacity when we can’t see it.
CC: Well, I think that one of the things I’ve learned in the last few years since taking a real fascination with midlife is the idea of the three stages of any transition you have in your life, and we call it the “anatomy of a transition” at our Modern Elder Academy, MEA. And this is based upon rites-of-passage initiation work, Joseph Campbell’s work, William Bridges’s, who wrote the book Transitions, work. So there’s these three stages to a transition. If you know these three stages, it does give you some comfort that there are coping mechanisms through the hardest parts.
So the first stage of any transition that you’re going through—whether that’s a divorce, changing your job, deciding to live in a new place, going through a health diagnosis that’s difficult—is you need to end something, and you need to actually then ideally ritualize that, whether that’s ritualizing that with other people or by yourself, being able to say, “That period of my life has ended, and I’m ready to move to the next stage.”
And for the caterpillar, that’s getting ready to plump up as it does for the last two weeks before it actually spins its chrysalis, and then it goes into the chrysalis and the chrysalis stage of life. What I like to now call the “midlife chrysalis,” not the “midlife crisis,” is that stage where it’s messy middle, it’s gooey, and in that goo it can feel dark and solitary and confining, and yet that’s where the metamorphosis happens, the transformation happens.
So what’s the coping mechanism in that second stage of letting go of something and then going in there? And the two things that you really need during that time are social support, no doubt. We need that for all the phases of any transition, but especially when you’re in the messy middle, because in the messy middle, it liquefies. And so you can feel very awkward because of the fact that the ground that you have tread on in the past is no longer there.
And so number one is social support helps you to have objectivity, but also have love, and then the other coping mechanism for that second stage is seeing the through line of your life, being able to see the themes and to understand what’s going to happen on the other side of this. Viktor Frankl famously wrote in Man’s Search for Meaning about the people who did not make it through the concentration camp. And it was often those who had actually lost a hope and a sense of meaning from this terrible experience of being in the concentration camp.
And when the kids in Thailand, the soccer players who got stuck in the cave, in the back of the cavern when the rains came up, and it’s been made into a movie, what the people who saved them had to do was take a rope and take it through the cavern, through all the water that had come up because of the rain. And it’s like that rope that you can understand the through line of your life, the thread that helps you to see where you are and where you might be going. That’s actually how they got the boys out of the cavern is having that rope. We need that rope in our own life.
And then the third stage of any transition is the beginning of something new. So it’s like, “OK, the caterpillar becomes a chrysalis, then it becomes a butterfly,” but when a butterfly actually emerges from the chrysalis, it’s got wet wings and it’s often on the ground before it’s flying. And so a growth mindset, a willingness to be a beginner, a willingness to look awkward, a willingness to laugh at ourselves because a growth mindset versus a fixed mindset means we’re more focused on improving ourselves than proving ourselves. And we’re not trying to win; we’re trying to learn. So long story short is that’s the framework I use in my own life, and it’s the framework we choose to use at MEA when people come focusing on how do they navigate their midlife transitions.
TS: Now you introduced this phrase in Learning to Love Midlife, the “TQ,” transitional IQ. Now, that’s very clever. I guess we can have all kinds of intelligences. So you’re describing here what the components are of having a high TQ.
CC: So the reason—and the reason we need a high TQ, Tami, is because both of my grandparents, both my grandfathers had the same job for 40 years. That’s crazy that both of them had—not the same job. They had their own jobs, but they had their own jobs for 40 years. One lived in Denver, one lived in Southern California. But if you look back in 1960, the average person had in the course of their lifetime three jobs. Today, we have 12 or 13. We also live in a world in which the world is changing faster and faster. So the idea that somehow we don’t have to get smart or wise around mastering transitions is silly. We really need to understand, how do you build your transitional intelligence in order to handle both the changes you make in your life volitionally, and then the ones that are thrust upon you?
And so especially for people in midlife, because one of the challenges we have often as we go into our 40s and 50s and 60s, we get calcified a little bit and we get stuck and we feel stuck based upon the mindset we have, our expectations of what we wanted in our lives. And we got to free ourselves from those things. Brené Brown talks about midlife being a time of unraveling, and I asked her, “Brené, that’s not—I don’t want to unravel. That sounds like you’re losing your mind.” She said, “Chip, have you ever looked in the dictionary under the word ‘ravel’? And something that’s raveled is so tightly wound that you can’t get it undone.” And that’s often how we feel in the middle of our lives. And so to unravel means you create some spaciousness, and in so doing, you create the opportunity for some new growth to happen. And you have to have some faith in this process too, because if you don’t have the faith, then it’s going to be really hard to go into that chrysalis in the first place.
TS: I want to talk a little bit about each of the three phases of transition. The first one, because OK, this is over, and what I realized recently in a transition that I’m going through is somebody said to me, “You haven’t fully accepted, Tami, that your reign in this capacity, R-E-I-G-N, is over. It’s over, period. It’s over, period.” And I stared at that sentence for a long time, and I was like, “No, I haven’t fully accepted that. No, I have not.” And I thought it sounds a lot easier sometimes to say something’s over, but all of us, 100% of us isn’t with that. And I’m wondering what you’ve learned about that. How do we get all of us to admit this X, Y, Z thing, it’s over?
CC: I’ll tell you what I did when we took out my prostate seven months ago. I had a prostate removal ritual with a few friends, and partly because I was lamenting the fact that—I won’t go into the gory details of what a prostate does, but there were a lot of bodily functions I was not going to have anymore. And so rather than sort of become comatose to it, instead I had a dinner with some friends and we talked about the value of our prostate in our lives. And that sounds ridiculous, but I think women do it when it comes to menopause more and more. This is not true five or ten years ago as much as it is today.
When I joined Airbnb after having been 24 years the CEO of my own company, the first two or three months were agony for me because I was reporting to Brian Chesky, the CEO, who was 31. And I was 52, but he was my mentee. I was mentoring him on being a CEO. For me, it was really hard to let go of being the person in charge of the company, even though it wasn’t my company that I’d started, but it was really hard. So I had to have a ritual. I had to have a dinner again with a few friends to say like, OK—we did a little exercise where each of us wanted to let go of something. For me, it was letting go of having to be the CEO, having to be the sage on the stage, and instead learning how to be the guide on the side. So what I did is I wrote a bunch of things on a piece of paper. We talked about it, and then I wrote on a piece of paper some of the character qualities that I needed to let go of if I was going to be successful at Airbnb. And then I also had to think about what I will replace those with. So for example, I am no longer the control addict. I no longer am the person who’s going to get all of the press around the company. I no longer am going to be the one who is managing meetings. And so as I started to get clear about the things that I used to do that I now was going to give up, and I put them on a piece of paper, and then each of us said, “Here’s the things we’re letting go of,” and then we lit the pieces of paper on fire in a little bowl, and then I actually said, “Here’s what I’m replacing it with.” That process was very valuable because it allowed me—a ritual allows you to see that transitional era, that period of time that is before and after.
And so from that point forward, I can’t say I was perfect at all those things, but I actually now had embraced them and I had spoken them out loud to other people. So you don’t have to do the exact ritual I’m talking about. We at MEA call this the “great midlife edit,” and we think you need to do it maybe once a year. It’s better than resolutions because at the end of the year, let go. Let go. At the end of the year, let go of whatever it is that you’re just ready to let go of, because don’t take that into the New Year.
TS: Why do you call it the “midlife edit”? You’re editing certain things out, or you’re putting things in as well?
CC: So the great midlife edit came from some of my scholarship with studying Carl Jung, but also long deep conversations with Richard Rohr. So Richard is an MEA alum. Amazingly at 78 he came to MEA, and he’s on our faculty. He’s teaching at our Santa Fe campus in July. And both of them said that the first half of your life is about accumulating, and the second half of your life is about editing. And one of the key talents that we need to learn in midlife is how to start letting go of the things that are no longer serving us, whether they’re mindsets, identities, roles, a narrative, a story that isn’t serving you anymore.
To be able to let go of those and just move on gives you the space for new things to come in, and so I don’t think just letting go alone is enough. I think actually then you say, “I’m going to replace it with such and such, and here’s the habits I’m going to put in place to do that.” But the reason I think why it’s important in midlife is because that’s sort of the era where you actually feel overburdened, and it’s 40s, 50s, 60s especially. No one says a 25-year-old’s downsizing, but you do say a 55-year-old or a 65-year-old is downsizing, and there’s a lot of reasons for that.
TS: In your blog, the Wisdom Well, you quote Father Richard Rohr, and you wrote this piece that really got my attention about the dark night of the ego, not the dark night of the soul. And I’m bringing that forward here in terms of this first phase of our transitional wisdom of being able to say, “OK, these things are ending.” And often what’s ending is some ego clinging of some kind, some ego framework, some ego identification. And I love the “dark night of the ego” because so many times I’ve heard people say, “I’m going through a dark night of the soul,” and I’ve had the thought, “Oh no, actually they’re just going through a dark night of the ego.” They’re having to let go of some of their big, cool accomplishment stuff or claims to fame or whatever, things that looked good. They’re basically in front of other people; things aren’t looking so great. This isn’t really what St. John of the Cross was talking about at a soul level, bare naked; it’s something else. And I was curious how you came up with that dark night of the ego. I thought it was really brilliant, Chip.
CC: Well, thanks. I looked at my own life. I looked at the times in my life where I felt things were the darkest. And at times it was circumstantial, at times it was, “This shit’s happening to me,” but a lot of it was really my perspective on it. And it had a lot to do with the things I was attached to, and especially my ego was attached to these things. I think that—gosh, who was it? I can’t remember the person’s name right now, but they said the key things, the “I am” statements that define us up through midlife often is “I am what I do,” “I am what I own,” “I am what others say about me,” and “I am what I control.” And these are “I am” statements that are very egocentric.
And I believe that what’s really happening, and Richard Rohr again speaks to this as well, is that there’s a primary operating system change that’s happening around midlife. You’re going from the ego to the soul, and the way I look at it—but no one gives us the new operating instructions for the soul, and so we’re sort of attached to the ego. The metaphor that I use now to think of this is that it’s like dancing in a sort of traditional hetero kind of way where the male is leading the dance, and through most of our first half of our life that is the ego, and the soul is really sort of following in heels and going backwards, and then it’s around midlife that all of a sudden something starts to stir inside of us. And we don’t have words for it often, but having had 4,000 people from 47 countries come to MEA and being there to observe and be an enlightened witness of them over the course of a weeklong workshop, I have seen it over and over again.
And what is going on is that the soul is starting to lead the dance, and the ego is a little awkward. The ego is not used to being the one in heels and going backwards, but over time, if the ego can learn to laugh at itself and the soul can actually use the magic of its connection to something much bigger than itself, miraculous things start to happen. Now, that sounds very woo-woo, but I will say that the research on a social science basis in terms of the kinds of transformations people go through often in their 40s, 50s, and 60s around ego to soul, there’s a lot of data on it and research work on it.
And I just love it because it described my life. I didn’t have language for this. I was going through a very difficult time, a dark night of the ego, in my late 40s. Everything that could go wrong was going wrong. My long-term relationship was ending, not by my choice. My African American foster son who was an adult was going to prison wrongfully. My company was running out of money during the Great Recession. I didn’t want to be CEO of that company anymore after running it for 22 years. I lost five friends to suicide, all of them men age 42 to 52. I had suicide ideation myself. And then I had a flatline experience at 47. I had a broken ankle and a bacterial infection in my leg, and I was on a strong antibiotic. And quite frankly, I had an allergic reaction to the antibiotic. And after giving a speech onstage, signing books, I slumped in my chair, and by the time the paramedics showed up to put me on a gurney and take me to the hospital, that was the first of nine times in 90 minutes that my heart stopped. So they had to get the paddles out, and they paddled me back to life.
So do you have to actually die like I did and come back to life—an NDE, near-death experience—to be able to make a transition or a transformation in your life? Of course not, but that one shocked me back into life. It was the classic hotelier’s wake-up call because I didn’t want to be a hotelier anymore. And so one of the good things about having an experience that puts you face-to-face with death is it radically shifts your thinking about how do you want to live your life?
So death is an amazing organizing principle for life, and there’s a bunch of work by Laura Carstensen from the Stanford Center on Longevity that has shown that when people have a shorter amount of time left to live, surprisingly on average, they feel happier. And part of the reason they feel happier is because they’re more in the moment and they’re not focused on the future. Future allows us to mind trip. And so for me, I all of a sudden went from, “Oh, future, future,” to like, “Oh, no, I’m in this moment. Every single day matters to me.” And it was in that kind of thinking that allowed me to wrestle control—I don’t want to say “wrestle”—but to surrender control from my ego to the soul, because I really felt like my ego had been not dancing very well, not leading very well. Does my ego still want to take over at times? Of course. I have a book coming out on Tuesday, and I want to have it do really well and et cetera. Those things still come up, but I can laugh at it now. And I don’t allow myself to get hijacked by my ego like I used to, or not as much. It still happens, but not as much.
TS: A couple questions here. When I imagined that a figure dancing backwards in high heels—
CC: Did you ever do that, Tami? I want to just understand—
TS: I’ve worn high heels on Halloween like once or something, and I kicked them off. I would say metaphorically, right here with you, I am definitely dancing backwards in high heels. And my question is, what happens when it comes up and you go, “I’m not sure everything’s going to be OK. Actually, I’m not sure it’s going to be OK. In fact, I think I could fall. I can’t dance very well like this. I’m not sure it’s going to be OK.”
CC: Well, I think then the question is like, what’s the biggest fear? What are the top three fears that are… Are you going to die? Are you going to lose your reputation? Are you going to have a financial meltdown? Are you going to lose a best friend? I think one of the things I’ve learned—I wrote a book called Emotional Equations, and one of the key things around anxiety is that it really comes from what we don’t know and what we can’t control. And so bringing to the forefront what it is that we have a fear is really an important piece of settling the anxiety.
So I guess what I would say is—so let me use an example. So MEA has a campus in Baja. We are opening a campus in Santa Fe, as you mentioned, a 2,600-acre regenerative horse ranch with two retreat centers on it. We have one retreat center down in Baja, now we’re going to have two on this ranch, and then we have another retreat center in the town of Santa Fe, an old Catholic retreat center in a seminary next to St. John’s College. So we’re growing big-time, and thank god there’s a lot of demand for midlife wisdom schools today, and we’re the first one. But this is the thing, but Tami, I will tell you, when I had my prostate taken out in June and found out I have to stay on this hormone depletion therapy so I have 1% of my normal testosterone, and I’m going to have to do seven and a half weeks of radiation right before the book comes out, right before the ranch opens, I was in the ego freak-out mode of like, “Oh my god, I’m going to have the last career I ever have in my life. I’m going to be a public failure, and I’m going to lose all my money,” and et cetera.
And I gave the ego some time to reflect on that, because it’s like, “What are you fearful about?” And then I really stepped in and just said, “So how can I reach out for help?” My archetype that defines me is my hero, and the hero has to go out and fucking do it by themselves, and that rugged individualist that was sort of drummed into me by my Marine captain father. And I came to realize like, “My god, I don’t have to do this by myself.” I can be a little bit more vulnerable in my blog about what I’m going through. I can be more open about saying, “I need your help.” And I can build relationships with people who are going to step up, and they just need a little bit of help on the front end.
And I feel so much better now. Oh my gosh, I was really in a dark place six months ago, but if I look back on it, it was really very much ego identified. And it was identified based upon an archetype of how I show up in the world, and I felt like I didn’t have the energy to show up in the way I have historically shown up. So the hero is something that I’ve had to dose down, not get rid of. It’s like I can be the hero occasionally, but I don’t have to have that be my primary archetype. I can be the jester occasionally, et cetera.
TS: I think you’re making such a good point because I think picking up the phone and calling people that we know love us, they love us for who we are, but we’re going to tell them, “I know you think I’m hugely successful in this way or that way, but the truth is this thing, it might not be working as well as I thought it was working and you guys all thought it was working.” And I don’t know, maybe that could be for some people about their relationship or something in their career or something about their money or something like that, and now we’re actually sharing with our friends the real struggle, and it’s like, “It’s OK for you to know me as this person who’s really struggling, even though you thought so highly about this aspect, and I’m willing to sacrifice that for you to know me.”
CC: And it’s beautiful because you open the door for them to be vulnerable too. And I’ve been doing a little bit of work with Dick Schwartz, who I know works with you, and his parts work, IFS. He’s actually on faculty; he’ll be teaching in Santa Fe this spring. And I came to see that I have many parts, but the three that I’ll just talk about for a second are I have Mr. Ambition and Mr. Ambition shows up because that’s really—when I came out as a gay man at 22, the number one thing my dad worried about, other than me getting AIDS, which I came out in 1983 at a time it was like, “Wow, not good timing,” was that I would want to be a hairdresser or a flower designer. I was the oldest child in the family, I was the only son, and I’m Stephen Townsend Conley Jr.—chip off the old block. So my dad’s biggest worry was that I wasn’t going to be ambitious, so there’s a part of me that’s just like, the part of me that is the ambitious one, and I get a lot of love and support for that. I am an admiration addict because I want you to love me for my ambition.
Then I have the creative part, and creativity really is something that I was very—I was charmed by my creativity when I was young, and I was very much a loner and a bit of a shy introvert, and I really appreciated that. And yet then as I moved into adolescence, I got this feeling like, “OK, that creative thing, maybe people think I’m gay if they see me as an artist, and so I got to be careful with that creative thing.” But as I came out at 22 and then got into boutique hotels and did all this and started to write and oh my god, those two together, ambition and creativity, like, “Whoa, that’s a potent combination.” But it can be a potent combination still full of ego.
And then there’s this other part, and I call this other part the “little one.” And the little one is just that little boy that—I felt timid, didn’t feel particularly lovable. And that little one quite frankly has been neglected my whole adult life. And so learning how to take these three, Mr. Ambition, creativity, and the little one, and give each one of them a voice and to see that maybe there’s some collaborations that can go on amongst them. And so for me, in my process of the last year, freaking out about what was on my plate at the same time I was dealing with a major health issue, stage III cancer, I had to let the little one speak more. And so the little one ended up speaking through me in my vulnerable Wisdom Well daily blog posts, and I’ve got one tomorrow for people who are listening. Go to MEA website or meawisdom.com or chipconley.com. Sign up to subscribe—it’s free—and take a look at my blog post tomorrow because tomorrow’s my last day of radiation.
So the blog post tomorrow is, “Is Cancer a Blessing or a Curse?” So it’s freaking my parents out, who are 86, and they’re like, “Chip, you are—way too much information.” But I guess there’s a part of me that feels like, “If I had in my childhood been able to express myself in this way, the little one had a voice…” I grew up in a family where children are seen but not heard, and that was sort of how I lived my life until I became much more extroverted in my teen years. I’m sorry that was long.
TS: No, first of all, I’m very happy to name these parts of you that, of course, from the outside I could see them. And from the outside, even our friends and everyone who we think we’re suddenly being very confessional with, they know what’s going on.
CC: They know, exactly.
TS: But we think we’re being so vulnerable to call and share and say, “I really need social support right now,” for whatever’s going on. People know it anyway. They can sort of smell it, which is—
CC: What are your parts?
TS: Whoa, whoa, whoa. We’re not going there right now.
CC: Oh, OK.
TS: Well, to be honest, I’m sorting it out. And I’m in a huge transition, and I think it would just take too long in our conversation for me, and it’s not as tidy as the way you presented it. But I’m definitely working through feeling good when I’m in control, and how do I feel good when I’m not in control, which is why I brought forward the high-heeled female figure dancing backwards. And you said, “Well, you have to admit to yourself what it is you’re afraid of.” Are you afraid of not being alive? I think was the first one you used, of dying, and I thought this is one of the things I want to learn more about from Chip because you had your flatline experience, which you shared with us, and now you’re going through treatment for stage III cancer for a difficult kind of cancer diagnosis. And I’m curious how you’re finding your way to dance backwards in high heels with your current health situation?
CC: So I’ll take it, I don’t have the blog post for tomorrow right up in front of me, but if I see cancer as a teacher and I don’t have to be the gladiator, the hero who’s going to kill cancer, but instead cancer is in my life for a reason, and the reason it’s in my life is because I’m supposed to learn something from this experience. We run a wisdom school, so I’m a big believer in understanding what wisdom is, and I believe that wisdom is our painful life lessons that are the raw material for our future wisdom.
So what I look at with cancer is being out of control is how am I supposed to learn from cancer? What are the key lessons? And some of my lessons have been things like I’m a pretty multidimensional person in terms of my interests. I’m not just Mr. Workaholic. I work workaholic hours though, and I have a calling, but I want to reinvest in the multidimensionality of my life, and so that’s one lesson. Another lesson was my body is a rental vehicle, and over time I care more about the inside of that rental vehicle than the outside, but I’m in harmony with my body. My body’s my best friend, and it is the rental vehicle that’s going to take me all the way to my death. And so how am I treating my body a little bit better? Of course, that’s a natural thing that would come from a cancer diagnosis. Another one is learning how to ask for help, and so cancer…
It was interesting that Lloyd Austin, the Secretary of Defense, had a prostate cancer diagnosis, didn’t tell his bosses—this is not political, this is just sort of interesting socially—and he not only did he not tell his bosses, but then he had some side effects of the radical prostatectomy that led to him being in intensive care in the hospital. And he wasn’t asking for help, and given the position he’s in, maybe he didn’t feel comfortable being public about it, but man, our shame that we have and things around sexuality and whether it’s breast cancer or prostate cancer or ovarian cancer or whatever it is, these are in some cases cancers that strike at the root of our gender relationship. And so when you have your prostate taken out, oh my god, there’s all kinds of things, the side effects of that.
All I can say is for myself to be able to be open to all of the emotions that I’m going to feel of having only 1% of my testosterone that I used to have, that can come back once I stop the ADT, but to not have some of the functioning that I used to have, man, these are things that I’ve had to just say, “How am I supposed to transition my romantic life? How am I supposed to”—and fortunately, I’m in a long-term relationship—but how am I supposed to transition my perspective on masculinity? And it’s been beautiful, and so for me, cancer has been a teacher. I am ready to graduate from this school, but it’s—
TS: Let me ask one clarifying question. When you said, “My body is my best friend,” because I can imagine that when people have any kind of disease diagnosis of something like that, there’s a feeling that your body has “betrayed” you, not it’s my best friend. So how—
CC: Or you have betrayed your body. That is where I was—Tami, you’re so good at this. That’s exactly where I was. My diagnosis got me to a place of saying, “My body’s betraying me,” or then, “Oh, I’ve betrayed my body,” as if they’re two different entities.
And so to get to a place where I say, “I am at one with my body, and my body and I have a beautiful friendship, relationship, in such ways that I am trying to be thoughtful about how I treat my body,” whether that’s drinking far less or at times not at all, whether that’s the kind of food I put in my body, whether that’s having a regimen of acupuncture and massage. And I don’t run as much as I used to, but I’m just a really avid walker and swimming and there’s all of that. But the one thing I want to say sort of as an adjunct to this is we are living in a culture right now that has the tech bros from Silicon Valley all focused on biohacking, as if somehow our body, if we just do the right things to it like a machine, it will live forever.
And the thing that’s so fascinating about this, Tami, is that the number one variable for living a longer, happier, healthier life based upon Blue Zones research, Harvard, Stanford, et cetera, is how invested are you in your social relationships in your 40s, 50s, and 60s? The people who are living late to 80s, 90s, and 100s are the ones who actually invested in their social relationships in their midlife. And so “illness” starts with the letter i and “wellness” starts with the letter we—letters we. And I deeply believe that that’s another part of the healing process for me is that sense of social wellness and allowing myself to be vulnerable enough and out of control to friends who are there to be my safety net.
And that’s not something easy for me to do, that’s for sure. I’m there for other people in their way when they’re going through their stuff, but when it’s for me, I want to go into my little chrysalis, in my little cocoon, and hide away. And I’ve done that this time, too, but I am just trying to break new ground and be that much more open to just saying, “Will you just come and take a nap with me?” Which is what I did yesterday with someone, because I didn’t really want to talk to them, but I actually wanted to just be in bed taking a nap with someone.
TS: Beautiful. I love that, Chip. Now, you shared with me these three phases of a transition, and we talked about ending and now we’re in the goo, for me, in the conversation, the gooey part. I think you’ve done a terrific job, really, of explaining the importance and the research behind social support. And then you said the second factor in getting through the goo is seeing the through line in our life, and you’ve shared a little bit about, by talking about your own parts, finding the through line. And then you asked me, and I was a little bit like—because I’m finding the through line, Chip, I’m finding it. What kinds of questions help people when they’re in the goo find the through lines in their life?
CC: Let me tell a story first, and then we can maybe go to some questions around that. So trying to learn how to let go of the way you’ve done things in the past. If you’re just letting go of it, but not actually replacing with something else, is like the classic person who’s retiring from something but not to something. And the problem for people who retire from something and not to something is they end up couch potatoes watching, on average in the US, 47 hours of TV a week. So that process of being in transition has got to be, yes, letting go, but also welcoming in.
And what I was able to do when I was at Airbnb, when I knew that I couldn’t be the CEO there, I didn’t want to be the CEO, and I didn’t want to be competing with Brian for that role—that’s what he was doing—is when I could finally see the through line of like, “Oh, you’ve called me the ‘modern elder’ here.” That was a gift, someone who’s as curious as they are wise. My role here is to learn how to be a master mentor and to be a “mentern,” a mentor and an intern, not just the person [who’s] Yoda or Dumbledore, whomever, but instead be the person who’s learning as much as he or she is teaching, and wisdom dispenser and seeker.
And so when I could actually get to that place of seeing the alchemy of curiosity and wisdom, that lit me up, because all of a sudden my role was not to have my photo on the cover of Fortune magazine. My role was to make sure that these three founders had their photo on that magazine and that when they do their IPO and are ringing the bell that they’re very successful. And Brian, over three years after the IPO went live and during a very difficult time of—Brian Chesky, that youngster who went to Rhode Island School of Design and had no business background at all, he’s still running one of the largest travel public companies in the world, and he’s the only Fortune 500 CEO who has a creative background.
So I would just start by saying, how do we look for the thing that takes what we have learned in our lives and allows it to have an evolution into something new? And so one of the questions we need to ask to get there is, clearly, what is the archetype or identity or role that has defined us that would not serve us moving forward? And we have to get rid of that, and we’ve talked about that. But then it’s actually literally doing a bit of a deeper dive of, what is it that’s your gift? The purpose of life is to find your gift, to discover your gift. The work of life is to develop it. And the meaning of life is to give it away.
One of the exercises we do at MEA is to help people try to find their essence, like what’s the gift? It starts from something that Peter Drucker did for companies. He used to say, “The most important question any organizational leader can ask is, ‘What business are we in?’” And ask it five times in a row, with the person who’s answering not being able to answer the same way twice. So we do that same exercise for people and we say, “What mastery or gift can you or do you offer?” And you can choose, like if you want to say, “Ah, I like the word ‘mastery.’” So what mastery can you offer? It would be perspective. And do you offer it? It would be like right now.
So if you could be asked that same question five times, “What mastery can you offer, Tami?” And then you would answer it, and I would say to you, “Thank you. Take a few deep breaths, close your eyes, open the channel. Be the conduit, not the can-do-it. Let something, be the conduit, come through you. Let me ask you again, Tami, what mastery can you offer?” And I can’t say that by the fifth time you answer that question, you have the light bulb over your head.
But I actually—the third time I ever did this exercise, I got to the fifth one saying, “I’m a social alchemist,” and like, whoa, that was it. I’m a mixologist of people. I love mixing people. That’s what MEA is all about, is how do you create the collective effervescence of a cohort coming together? And it’s a potent cocktail. And so it has helped me as a filter to understand how I’m living my life moving forward. So trying to understand your gift, getting it down to some language that allows you to see that, and then to say, “That’s the flashlight that is going to help you out of this messy middle, this dark place.”
Because actually what is often the case, and this may be the case for you, is you’re clinging to something that has worked for you all the way up to now, but it may not work for you moving forward. And it’s partly because you’re not using your imagination. And in the chrysalis, the literal biology of it is there’s these imaginal cells that were in the caterpillar that are also in the butterfly. And so it’s the imaginal cells, imagination in the chrysalis, imagination in midlife, that allows you to say like, “Oh, OK, I’m letting go of that and now I’m going to go to this.” And it’s not easy, but that’s why the social support’s helpful in that era.
TS: Let me just be dark for a moment.
CC: That’s fine.
TS: People use the butterfly metaphor all the time. At one point I heard, “Not all of the caterpillars who turn into goo make it out as butterflies. Some goo just dissolves into goo and stays goo. Period.”
CC: Yes.
TS: And that’s a dark thing to learn when you’re studying a metaphor like this. I liked it better when I didn’t understand it that well, and I thought, “Every single caterpillar comes out as a butterfly.” It’s like, “No, some don’t make it.”
CC: That’s true. So there’s no guarantees in life. The metaphor is helpful as a way, especially when you’re in the most challenging place, which is moving from the ending to the middle, going from caterpillar to chrysalis, that there can be hope. But not all those people in the concentration camp that Viktor Frankl was hanging out with made it to the other side, and again, those who did, from Frankl’s perspective based upon what he wrote in Man’s Search for Meaning, were those who were able to find the through line, the hope, and the meaning.
So despair equals suffering minus meaning. So suffering is an ever-present part of our life, especially in the first noble truth of Buddhism. And despair and meaning are sort of inversely proportional—yeah, inversely proportional, exactly. So I am not trying to be a Pollyanna here. There are going to be butterflies that never make it out of the chrysalis. There are going to be butterflies that end up on the floor and get squished. So don’t use the metaphor if it doesn’t work for you. At the same time, I do believe the three stages make sense, and for a lot of people who get into that dark place and get stuck in the goo, they are in that second stage.
TS: Now, when I asked you about TQ, you said, “Yeah, is something we’re all going to have to get good at because of the time that we’re living in.” And in your new book, Learning to Love Midlife, you define midlife as a really large age range. I think at one point it was between 35 and 75, potentially you could be in the midlife passage. And I thought, “That’s such a long period of time.” It almost makes it seem like what? That’s like—
CC: When I was researching the book, I spent a lot of time talking to academics. First of all, midlife as a life stage is so under-researched. There’s just been not a lot of research on it. There’s a lot of research at later life, a lot of research for early life and adolescence, and now emerging adulthood from 18 to 30, but not a ton around midlife. So talking to the scholars around midlife, what people said to me sort of over and over again was, “If we are living in an era where people are living longer”—
And let’s be clear, in the US, longevity is in a really big rut right now. We have the same longevity today that we had in 1996. That is not true in the rest of the world. We are pretty much the only country that is at the same level as 1996. The rest of the world is flourishing in terms of its longevity.
So if we are living longer on average globally, and the percentage of people who are centenarians in the world is growing fast, it is possible that midlife lasts maybe as long as 75, because a lot of people are going to be full career into their mid-70s. And the 35 is sort of a function of the fact that there’s a growing number of people who are fearful for their jobs being obsolescent because of digital intelligence and technology, but now especially artificial intelligence.
So 35 to 75 is a long time, but let me break it up into three pieces of midlife. And again, I worked with academics on this, so Stanford, Harvard, UC Berkeley, and Yale. 35 to 50 is sort of early midlife. And what’s notable about this early midlife period is it’s a time when you feel a bit overwhelmed. You are in the early stages of maybe feeling some disappointment. You may feel like you are stuck on a treadmill that was not your treadmill; it was your parents’ treadmill. And you are afflicted by success-ism, thinking success will make you happy. And so 35 to 50 is actually a really rough period. The U curve of happiness research, social science research, shows that that’s really the least happy time for adults.
And then 50 to 60 is core midlife, in my opinion. Core midlife means you have started to do a major transition. And whether that transition is spiritual or it’s cultural or it’s emotional or it’s career-wise, vocational—physical for sure. Menopause for women often is 45 to 55, but it can be all over that, and perimenopause, all of that, is happening during this era. And so core midlife is a period where you start to realize from 50 to 60 that you’re in the afternoon of your life, as Carl Jung would say. And Carl Jung said, “You can’t live the afternoon of your life based on the rules of the morning,” and the rules of the morning is maybe early midlife and earlier.
And then later midlife, in my opinion, is 60 to 75. And I’m 63, and so I’m in that period. And what’s going on in later midlife is you’re starting to realize you are preparing for your senior years. And who knows what we call those senior years. I’m going to call them “senior years” now because I don’t have a better name for them. But from 75 on, there is some evidence that your happiness starts to plateau and maybe in your 80s it starts to decline. Now, if you talk to the U curve of happiness researchers, they disagree with me. But I see my own parents, so I know that they were at peak level of happiness in their late 70s, and their 80s have been tough because you start being more infirm and things start to break down more. But if you listen to Laura Carstensen at Stanford, she’ll tell you, “Hey, again, the shorter amount of time you have left in your life, the more you’re in that moment and you’re not focused on the future.”
So that’s my perspective on midlife is that there’s three stages of it, and there’s sort of a general prescription of each. But I’m also a believer in age fluidity. When you’re age fluid, there’s no age or generation that really defines you. You are all the ages you’ve ever been and ever will be, and I sort of like that, too.
TS: So in terms of this notion of the midlife chrysalis, from crisis to chrysalis, it’s possible that you could have a midlife chrysalis, going through that experience in each of the three phases, or you could have it multiple times in the phases. I think previously I thought like, “Oh, you go through your midlife crisis once,” but after reading your book, Learning to Love Midlife, and reflecting on my own life, where I am now, et cetera, I thought, “God, how many of these chrysalis experiences am I going to go through in my life?” Obviously several.
CC: Bruce Feiler, who wrote the book Life Is in the Transitions and is on our MEA faculty, calls that the “lifequake,” when you’re going through maybe multiple transitions at once or you’re going through a series of them. And one of them, you might be in the ending period, like a divorce. And another one, you might be in a beginning period where it’s a new career or you’re moved to a new place or you’re an empty nester for the first time. So the reality is each of these three stages are relevant to each kind of transition you’re going through. And when you’re going through multiple transitions at once, it’s a little complicated. But yes, I don’t think it’s all linear.
And I do love millennials and Gen Zers who have taught me that the tyranny of the three-stage life that I was sort of brought up with, and you were too, was you learn till you’re 20 or 25, you earn till your 60 or 65, and then you adjourn or retire till you die. No more of that, because let’s take a sabbatical at age 40, if you can afford to. Let’s go back and go to graduate school at 45. Let’s become polyamorous in your marriage at 50. And let’s be open to the idea that you can be an evolutionary being that is constantly learning something new. The number one question we need to ask ourselves is, what in our life are we a beginner at today? And that is a more important question to ask in midlife and beyond than it is even earlier in life.
TS: You write beautifully about how you started surfing.
CC: A question that we need to ask ourselves is, what is it that we know now or have done now that we wish we’d known or done ten years ago? And then once you know that—what is it that I will regret if I don’t learn it or do it now? And at 57, living in Mexico, living in Baja, starting the MEA campus there—I didn’t learn Spanish growing up. I learned French, hence the name Joie de Vivre for my company.
And so as I was thinking at 57, “Well, at 67, it’s going to be harder to learn Spanish and harder to learn how to surf,” because I live on a beach where there’s a surf break. “Why don’t I learn now?” Because anticipated regret is a form of wisdom, and to be able to look out there and say, “At 67, ten years from now, I will regret if I don’t do this now,” that’s what got me off of my butt and helped me start to learn Spanish and start to learn to surf. I’m not very good at either, but the fact that I started to try is a form of a growth mindset, and we need that. We need curiosity and an openness to new experiences our whole life.
TS: Here’s the last thing I want to talk about, Chip, because you mentioned how when we let go and we let die these ego investments and we’re able to make it through the goo, there are these new beginnings, new birth. We could call it our “soul life,” this journey we’ve been talking about from ego to soul. And I’d love to know, here you are, having gone through just recently this huge health travail that you’re in the middle of, when you think of, “This is what my soul life is, this is what springs forth that is so genuine for me, that’s filled with newness,” what comes up for you?
CC: So what comes up for me is something—I mentioned earlier Erickson and “I am my work” and et cetera. What he also said was, “As we turn to this age, the ‘I am’ statement is, ‘I am what survives me.’” That’s what, for a while, my soul was saying to me, “I am what survives me. What will survive me?” But then I had a hard time with that on some level because I was like, “Well, I don’t want my name on a building, and I don’t want to feel like there’s an ego attached to legacy, for example.” So the thing that speaks to my soul today is “I am how I serve.” I am how I serve. And I’m not suggesting that has to be somebody else’s “I am” statement. But when I get connected to that language, “I am how I serve,” it allows me to get to a place of humility and to a place of wanting to give back. And that’s when I know my soul feels well adjusted. I have opened up this channel that’s supposed to come through me, and my role here in life is to serve.
How do you know if you’re on the right path? You feel the goosebumps. You notice people out there that you might not have noticed in the past, because they are a role model for you. You hear something or you’re attracted to something that wouldn’t have been interesting to you in the past. And so for me, I’ve been really fascinated by talking to nurses and teachers who they’re in the serving profession. And I’m a hospitality guy, so of course we were in the serving profession, too. But when someone’s a teacher or a nurse, often it’s a calling for them that came from something really from childhood, and I just love listening to teachers and nurses. If you’d asked me that 15 years ago, I would not have enjoyed that. I would’ve asked the question, “So how’s that serving me? How is it serving me to listen to teachers and nurses?” And now I just realize that they are my role models. And so I know the goosebumps are the physical reaction to the sense I’m on the right path.
TS: I’ve been speaking with Chip Conley, someone who carries the medicine of the Phoenix, the power of the Phoenix, very high TQ, intelligence to go through all kinds of transitions. He’s the author of the new book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. The founder of the Modern Elder Academy. Chip, I always love being with you.
CC: Thank you, Tami. I love being with you, too.
TS: You make my heart swell. Thank you.
CC: Well, we learn from each other. You and I have such phenomenally similar stories in certain ways, and so I appreciate that we are on this learning journey together.
TS: And if you’d like to watch Insights at the Edge on video and participate in the aftershow Q&A session with our guests, come join us on Sounds True One, a new membership community featuring award-winning original shows, live classes, community learning, guided meditations, and more with the leading wisdom teachers of our time. Use promo code PODCAST to get your first month free. You can learn more at join.soundstrue.com. Sounds True: waking up the world.
