Chip Conley: A Modern Elder at Work

Tami Simon: Welcome to Insights at the Edge, produced by Sounds True. My name’s Tami Simon, I’m the founder of Sounds True, and I’d love to take a moment to introduce you to the new Sounds True Foundation. The Sounds True Foundation is dedicated to creating a wiser and kinder world by making transformational education widely available. We want everyone to have access to transformational tools such as mindfulness, emotional awareness, and self-compassion regardless of financial, social, or physical challenges. The Sounds True Foundation is a nonprofit dedicated to providing these transformational tools to communities in need, including at-risk youth, prisoners, veterans, and those in developing countries. If you’d like to learn more or feel inspired to become a supporter, please visit

You’re listening to Insights at the Edge. Today my guest is Chip Conley. Chip is a hospitality entrepreneur and New York Times bestselling author. He’s the founder of Joie de Vivre Hospitality and served as Airbnb’s head of global hospitality and strategy for four years. Today he acts as the company’s strategic advisor for hospitality and leadership. His five books have made him a leading authority at the intersection of psychology and business. Chip was awarded Most Innovative CEO by the San Francisco Business Times and is the recipient of hospitality’s highest honor, the Pioneer Award, and holds a BA and MBA from Stanford University. Chip Conley is also a presenter in Sounds True’s Inner MBA, which is a new, nine-month immersion training program that begins in September that Sounds True is creating in partnership with LinkedIn, Wisdom 2.0, and NYU. Graduates of the Inner MBA receive a certificate of completion from NYU, and if you want to learn more about the Inner MBA, please visit

I feel a remarkable amount of resonance with Chip Conley. Quite honestly, he feels like soul family to me in a certain kind of way—our emphasis on bringing our true hearts and our true selves to work and making a contribution and continuing to do so into our later years. Here’s my conversation with Chip Conley:

It’s great, Chip, to have this chance to talk to you and I’m so happy that our lives have finally converged in such a way that you’ll be participating in this new Inner MBA program that Sounds True is producing, it’s wonderful to have you be a part of that.

Chip Conley: I’m thrilled. You know, you and I have a lot of history. How long has Sounds True been around?

TS: 35 years!

CC: 35 years and I started my boutique hotel company, which I sold, about 33 years ago. So you and I were really early pioneers as socially responsible entrepreneurs and I just have loved watching your path of travel, my dear.

TS: That’s great.

CC: You’ve been an inspiration for me.

TS: Well that’s kind of you to say that. You know, I wanted to start by calling you a philosopher businessperson; I came up with that term in preparing for this conversation and I was looking at all the things you’ve accomplished and the books you’ve written and that seemed to me to be the thread going through it all, this idea that you’re functioning as a philosopher businessperson in the world and I’m curious what you think about that.

CC: I love it, I’ll own it. Yes. Well I think what’s interesting about philosophy is it’s really wedded to understanding the human soul and maybe the existential reasons we’re here on earth, which is not exactly what business can sometimes be about. It can be very short-term-minded and profit-minded. But what I’ve liked doing is probably mixing a little bit of philosophy, a little bit of psychology, and a little bit of business into this mix that says, why would the place we spend most of our waking hours not be the place where we find our own form of enlightenment or personal growth or a feeling of self-actualization? So, yes. I love philosophy, I’ve got lots of philosophy books down in Baja at my Modern Elder Academy library, so guilty as charged.

TS: OK. And you talked about how traditionally in business, there’s a focus on short-term results and how—you know, here I’ve been at this for 35 years, clearly it’s not about short-term results. But how else would a business have to change its outlook to incorporate some of the most important discoveries that you’ve made in your life and that you’ve written about in your books from psychology and philosophy? I know this is a big, fat, softball-type question, but how does business have to change to come into alignment with wisdom?

CC: I think that the way that business needs to change is to recognize that the way that we get to a sustainable, long-term path of success—and I’m defining sustainability as not necessarily the ecological and environmental side of it, although that’s certainly part of it as well, but it’s more the human side of it. To create a long-term success that’s sustainable, it better be built on some foundational principles that are human-centered. So for me, two psychologists, two great Jewish psychologists, I never met either one of them, but I’ve sort of been on the couch learning from them, just reading all their books and studying them and then writing books myself about them. Abraham Maslow and his hierarchy of needs had a huge influence on my thinking as I founded and was CEO for 24 years of Joie de Vivre Hospitality, which is a boutique hotel company that became the second largest boutique hotel company in the US. So this hierarchy of needs, if you apply the hierarchy of needs to employees, customers, and investors, what would that look like?

That’s part of what I used, and then Viktor Frankl’s work, another psychologist but frankly Frankl is almost an existential philosopher because his whole perspective on life was really forged frankly before he went into a concentration camp. He was a Jewish psychologist from Vienna, but he, while in a concentration camp, really learned that meaning and hope and having a sense of a future was frankly more pivotal to peoples’ sense of their ability to live, so it’s almost like meaning was a fuel for life. Well, Frankl’s perspective on meaning and Maslow’s perspective on personal development both have influenced the kinds of companies that I’ve been involved with—my own company, but also for the last seven years, Airbnb, as the in house mentor to Brian Chesky the cofounder and CEO, for four years in a full-time role and the last three years as a strategic advisor. But I think at the end of the day, it is recognizing that humanity is the glue that keeps companies together even in an increasingly AI-centric world. And so it’s those human principles around psychology and philosophy that have been foundational to my way of leading.

TS: OK, and just to make this very clear for our listeners so that they get the real takeaways, in your book, Peak, you write about Maslow’s model and how to apply it to business. What are the most important, pith discoveries that people need to know from applying Maslow’s hierarchy of needs to business?

CC: We’ll focus on maybe two of the three pyramids just to keep it brief. The first one is the employee pyramid, and if you took Maslow’s five-level pyramid of physiological needs all the way up to self-actualization—those are the first and the fifth levels. But if you distilled it down to three basic principles, it’s what I call the transformation pyramid which is survival is at the base, success is in the middle, and transformation or transform is at the top. And if you applied that three-level transformation pyramid of survival, success, transform to employees, it would be money at the base, recognition in the middle, and meaning at the top. So most companies think that the primary reason their employees leave the job is because of compensation issues and it’s really the fourth most likely reason a person leaves a job. The number one reason a person leaves their job is usually because of their boss or the way they feel they’re treated in the company and so that’s why recognition is sort of that success level of the employee pyramid.

Very few companies really look at this idea of meaning. How do you use meaning? Which, meaning creates inspiration and inspiration is like an intrinsic motivator as opposed to an extrinsic motivator. The first two, money and recognition, are like, “All right, I’ll give you some more money or some more recognition you’ll do a better job for me.” Whereas if I give you some more meaning, it’s really coming from internally within the person, it’s less of a bartering game.

And great companies, I think, do two things when it comes to meaning. They actually help people feel a sense of meaning in the purpose of the company, but they also feel the sense of the work they do every day is influencing that purpose. Many companies that are, say, socially responsible, do the first piece pretty well. They have a noble goal, a noble mission. Many companies don’t do the second one well, which is how do you help a bookkeeper or someone doing HR or someone doing janitorial duties, how do you have that person—for me as a hotelier, how do I have our maids cleaning toilets each day feel a sense that the work that they do every day has an impact on what was our noble purpose, [which] was to create joy because the company was called Joie de Vivre, which is French for “joy of life.”

So I’ll just say one quick thought on that, is, the way we were able to address that was—it’s so simple, have your customers come in and talk to your employees. So once a month we’d have a staff meeting, and at the staff meeting we would invite a customer, a loyal customer who happened to be staying in the hotel right now, to come and spend ten minutes talking about why they loved that particular hotel. And then we would ask that customer to call out two or three employees because of the specific actions they had taken over the course of many stays that that guest had stayed there, and to actually hear it from your customer, it was a great way of our staff feeling, “Ah, OK, I really appreciate it.” Even when, in one case I remember, a woman came in and she had an accounting issue and it was somebody in our accounting department who solved something for them. Because it’s usually our customer-facing people who got called out, but I loved it when it was somebody from a non-customer-facing piece of the business because it helped them to understand that they have an impact as well.

So that’s the employee pyramid. I could give you the customer pyramid too, or you could—

TS: Yes! Yes, go for it. Go for it.

CC: So the customer pyramid—if you think of the customer pyramid, this is relevant whether you’re a dry cleaner or a defense contractor. So, there’s three levels to this: at the base of the pyramid is survival, which is meeting expectations. The middle of the pyramid is the success part, which is about meeting their desires, and at the top of the pyramid, the transformational part of the customer pyramid, is meeting the customer’s unrecognized needs. So, expectation’s at the base, desire is in the middle, unrecognized needs at the top.

How is this important? Well generally speaking, most companies get really fixated on benchmarking themselves with their competition, and that’s usually at the base of the pyramid because frankly, the things that are easiest to measure are at the base of the pyramid. But when you move up this pyramid, you’re moving from sort of the commodity to the more differentiated, and truly that’s where the loyalty happens. And great companies are so good at what they do that they almost understand the needs of the customers. They can mind-read their customers in such a way that even without a focus group, or even with a focus group and they never heard something, they can surmise an unrecognized need of a customer.

So how does that play out in reality? Well, we had a hotel for example that’s called the Hotel Vitale, it’s in San Francisco on the waterfront, and we knew—this was 20 years ago—we knew that there was a growing demand for people who want to stay healthy when they’re on the road. But most business-class hotels didn’t focus on that, nor did they focus on business women traveling. So most business hotels, especially 20 years ago, felt like it was a men’s club almost.

And so we decided to create a yoga studio on the top floor, the penthouse level of the hotel, with an outdoor terrace facing the bay, and have free one-hour yoga classes each morning. Short enough so people could actually go do yoga and then go to work. And I can’t tell you how hard it was to convince my investors on this, 20 years ago, to do this. I mean, today, you can see it. You can see a financial district hotel with a yoga studio. But 20 years ago, they’re like “nobody’s ever done this before and your guest comment cards, no one has ever asked for this.”

But what we saw was the toil and the toll that travel was taking on business people. And the fact that there were a larger number of business women traveling, many of whom did yoga, meant that we were offering something that hadn’t been offered before and nobody had asked for it, but it was an unrecognized need of our customers.

And I’ll never forget the email I got from a woman who just said, “Listen, in the past when I had stayed in the hotel in San Francisco, I’d walk ten blocks to a yoga studio or get a taxi there. I’d come out, and I’d be all sweaty, and it’d be impossible to get a taxi.” And again this is years ago, before ride-sharing existed. “And so I’d have to like, run home to the hotel. By the time I got back to the hotel, I was stressed out because I knew I was going to be late for my meeting.” So it’s interesting when you hit on something that’s an unrecognized need, something that’s transformational to a customer, they become your evangelists and you don’t have to spend nearly as much money on marketing.

TS: I love that, and I want to go right for what I think could be an unmet need of the podcast listener, right now. Which is, when I hear people talk about meaning, and meaning in business in the way that you’ve talked about it, a lot of Sounds True authors talk about purpose and how people become so lit up when they’re on purpose and they’re contributing to the lives of others and in the workplace when you’re connecting people to the purpose of the company, I get that. But my question, and this is the unmet need, is one thing I’ve found in my life—and I’m curious Chip as someone who’s accomplished so much, is that, whenever I define meaning as something about an accomplishment, something I’m contributing to the world, something I’m giving to other people, it fulfills me to a degree and provides a degree of meaning, but there’s a bunch of meaning in life that isn’t touched by that. And I wonder if you can comment on that from your own experience.

CC: Yes. This is the TED talk I gave in 2010, which is I went to Bhutan to study the Gross National Happiness Index about ten years ago because I was fascinated by, like, how do you measure something that’s so intangible? Because it is true that, yes you can have a sense of purpose and meaning when you’re going out and doing good works in the world and you can sort of get a sense of what the metrics are in that. But what happens when the thing that really lights you up is something that’s actually almost unexplainable? Or certainly immeasurable?

So what I would just say on that is—and I’ve been learning at our Modern Elder Academy, which we’ll talk about I’m sure—the number one thing is learning how to just have my own personal barometer for what in my early life was happiness and in my later life is contentment, around the way I feel like I’m influencing people and the world. It’s like having an internal thermometer and being able to tap into it and know when it’s beyond ego and beyond a sense of altruism, it’s truly coming from almost a place of pure love.

And this is an interesting… we’re not maybe ready for segueing into Modern Elder Academy but this is exactly why I do what I do down there, because I feel that ephemeral sense of collective effervescence, which is a term that’s 110 years old from French sociologist Émile Durkheim when he studied religious pilgrimages. And it’s the sense that you have your own sense of ego and separation somehow seems to evaporate and what comes in its place is this communal joy. No one’s ever been able to measure collective effervescence but when you feel it, there’s a glow and a buzz and a feeling of being in the flow.

So sometimes to understand whether you’re in that, you truly lose track of time. It’s like what Mihaly Csikszentmihalyi’s written about with flow and others have talked about, about being in the zone: you’re usually in almost a state of timeless awareness. When I’m feeling that, my God, I feel like I have gotten the true fuel inside of me which has nothing to do with winning an award for being a socially responsible entrepreneur or feeling like wow, we’re able to get 1000 volunteers to help wrap Christmas presents for people. I mean all of that’s great, but when you’re in that true sense that you’re connected on a deeper level with the people that you’re in this experience with, I could live the rest of my life on that. That’s the thing that would keep me alive in a concentration camp as well.

TS: Can you give an example of feeling collective effervescence?

CC: Yes. So do you mind if I talk about the Modern Elder Academy?

TS: No, I want to talk about the Modern Elder Academy.

CC: OK. So let me give a tiny bit of background first and then I’ll explain. So I sent a bunch of years as the Boomer amongst the Millennials at Airbnb in the early days of Airbnb and helped the company become a mainstream hospitality brand globally. And what I learned along the way is that a modern elder is different than a traditional elder. First of all, the word “elder” is a relative term; it depends on who you’re surrounded by. Elderly depends on what part of your life you’re in, if you’re in your last five or ten years of your life you’re probably elderly. But if you’re an elder, you could be an elder at 45 if you’re surrounded by 25-year-olds. So I was in my 50s surrounded by people in their 20s and early 30s, and I found that a modern elder is as curious as they are wise. Ultimately, I decided wow, we don’t have schools for people in midlife and we’re going to live longer, power’s moving younger, and the world is changing faster, and so we need a place where people can learn how to press the reset button and repurpose themselves.

So we created this four-acre campus on the beach an hour north of Cabo San Lucas in Baja California Sur in Southern Baja in Mexico. So we’ve had about 650 people from 22 countries come through the week-long program. What I feel when people come and do a week-long program and they are in this liminal state—so liminality is when you’re in transition between two things. So they’re in a transitional state because our whole philosophy is, how do we help people in midlife, defined broadly from 35 to 75, move through midlife transitions? Because we have had a long history as a society of creating rites of passage and celebrations for people through puberty and adolescence to adulthood and marriage and baby showers and funerals, but we don’t really have anything in the way of rites of passage in midlife even though there’s all kinds of things people go through.

So this process of people getting vulnerable and being open to talking about a health diagnosis or your parents passing away or empty nest syndrome or knowing they need to change their career because at age 46 they feel obsolescent in the tech industry or in advertising, or someone’s recently divorced.

We get people and they find that they came prepared with all of their baggage to sort of talk about what they’re going through, and what they realize over the course of the week is how they are taking off the costumes. No one had realized how many identities or mindsets they were wearing in their lives. And we get a little bit elemental and we use nature as a teacher because we’re truly in the desert and in farmland, we’re in a very rural area right on the beach. So there’s just a sense that people somehow—what we’ve been told is that it’s a process of humaning, and in that process of humaning where people actually feel that sense of truly elementally being back to what defines them uniquely but also what connects them with each other, these 18–20 people in the cohort find that all the judgment that they walked into the workshop with, the judgment toward themselves but also how they judged each other the first night as we were getting into orientation, somehow that evaporates and what emerges in its place is this common sense of humanity and the mirror neurons in our brains start to actually dance with these other people.

And the thing that comes out of that is this common sense of the fact that we have so much in common. There’s a common sense of our humanity and what we struggle with and what we call the great midlife edit, all the things that we need to remove from our lives. So psychologist Carl Jung basically said, paraphrasing him, that you can’t live the afternoon of your life based on the rules of the morning, and yet we don’t have anything in the way of schools or tools for people in what we call middle-essence, an era of life quite like adolescence in that you’re going through emotional and hormonal changes. But we don’t really help people through that.

So, after a week I see this collective effervescence in peoples’ faces, in their eyes, in their sense of connection with each other. So back to the original premise here, I get so lit up and feel the sense of radiance being in a room with a collection of people who feel so alive. Joseph Campbell said people are not so much looking for meaning in their life, they’re looking for the sense of being fully alive, and that’s what we see by the end of the week. And it’s a social enterprise so I don’t make a dime—I don’t pay any rent for the four-acre campus I’ve built, 63 percent of the people in our first year were on a scholarship of some kind that we gave them. So it’s the world’s first midlife wisdom school and we live in an era where people think knowledge and wisdom are the same thing, and they’re really not. And so we’re just helping people to cultivate and harvest their wisdom.

TS: Now this phrase, “collective effervescence,” I want to focus in on the “effervescence” part.

CC: Yes.

TS: Because that’s what feels like the solution of the meaning crisis to me, just like the Joseph Campbell quote you just referred to. When I feel that—and I’m going to come forward here a little bit and share that sometimes I can feel almost like there’s a fountain turned on, on the inside. And I don’t hear that many people talking about it, Chip, and in fact I’ve never talked about it on Insights at the Edge before, this secret fountain, but this is the moment. And when that fountain is on inside . . . I think it’s on all the time but I don’t always feel it because I’m thinking about this or problem-solving that or involved in so many things, but when I feel it, the question of meaning goes away. It goes away. And now you’re talking about sharing that feeling in a group. That’s very powerful, that you’ve focused in on that.

CC: So there’s an interesting theme here because J.D. Salinger, the author, long ago wrote, “happiness is a solid and joy is a liquid,” and my company was called Joie de Vivre and I’ve always been fascinated by joy as opposed to happiness. Happiness can often be circumstantial, and joy is this bubbly brook inside of you. It’s something that feels like a fountain. So no one says that they’re happiness-filled but they do say they’re joy-filled. To be joy-filled means there is something inside of you, it’s a liquid—again, happiness is a solid, joy is a liquid. It’s a liquid inside of you that’s bubbling up. What’s fascinating is when you can be in community with a collection of people who are feeling that same bubbling and there’s the reflection of that with each other, and this is without any mind-altering substances.

So people sometimes feel it—it’s part of the reason a few years ago, after I had sold Joie de Vivre, and before I was asked by the three founders of Airbnb to join the company, I created a website called Fest300 dedicated to creating an annual list of the 300 best festivals around the world because I was fascinated by the more digital we get, the more ritual we need. And so we’re awash in URLs but what people needed was IRLs, they need this “in real life” experience.

So in the last 15 years, the number of festivals in the world and the attendance in festivals of all kinds—religious pilgrimages, music festivals, cultural festivals, film festivals—have escalated quite a bit. And I’ve been on the board of the Burning Man Project, Burning Man I was a founding board member of the nonprofit, so been involved with that organization for 20 years and on the board for 10; and so I was like, “OK, collective effervescence, that’s what people are feeling at Burning Man.”

But the question was, how do you take it from a place like Burning Man—or I went to Maha Kumbh Mela, which is the largest collection of humanity in the world on the Ganges River every 12 years, 100 million people come together and it’s a 55 day–long festival. It’s like wow, that was crazy, but how do you take that and then bring it back into your life? And that’s really what we’ve tried to do with the Modern Elder Academy in ways that create practices and habits that people could actually take back into their life. But yeah, I do agree with you, this idea of this bubbly flavor inside of you. What’s magical is when you actually feel like it’s becoming even more bubbly because of the people around you.

TS: Now you know, it’s interesting when you give an example of being at a festival or even the example of being at the Modern Elder Academy, it’s relatively easy for me to imagine feeling this collective effervescence with other people. We started our conversation by talking about W-O-R-K, a heavy four-letter word that doesn’t seem to go naturally with a notion like C-E, collective effervescence. Do you think it’s possible?

CC: I don’t think it’s possible to have it every day. I do think it’s possible, though, to feel it for sure and the reason a person would feel a sense of collective effervescence in a workplace is when they feel like the combination of the meaning in work and the meaning at work are working. And meaning at work basically means the purpose of the organization feels like it is elevating you, giving you a sense of elevation. And then meaning in work is the work that you do every day. The fact is that work has a certain amount of drudgery built into it, but the difference between a job, a career, and a calling is really the difference between moving up that Maslow pyramid from your compensation package or money, to recognition being a career, and a calling being meaning.

So how do you do it? How would you create an organization that felt like that? It would be where the full pyramid would actually be well covered, so people feel that they’re compensated enough that they feel respected and they felt like their compensation’s fair. But if compensation’s too predominant here, whether you’re a housekeeper working in San Francisco and it’s really extremely expensive, and therefore the money part of that pyramid is 90 percent of your pyramid because it’s hard to pay the rent, or whether you’re an investment banker who’s just obsessed with money, if money takes up the whole pyramid it’s a problem. So I think it’s harder to be in collective effervescence in those environments. But when you create an environment where you move up the pyramid from money to this next level of recognition, you feel recognized but you’re also recognizing others, how do you create an organization where people feel recognized?

So let me give you one example because I think what you’re looking for here, Tami, is what are some practical ways to apply this?

TS: Yes.

CC: So one of things we did in the dot-com bust, 2001 to 2005 in the Bay Area, we were the largest independent hotelier in the Bay Area at the time, so we were very vulnerable. And one of the things we did is we had a weekly meeting of our leadership team for the company, about twelve of us, and it was usually a two-hour meeting, and during that really big downturn it was a pretty depressing meeting because there was lots of bad news.

Well, what we did is we actually decided to take the last ten minutes of the two-hour meeting and have each of us bring up someone on our team out there in the field, who’d done something that deserved some recognition. And it would be just a specific little example, and in so doing—so I’ll give you an example. So we had a hotel called the Hotel Rex and there was just one elevator in the hotel and almost a hundred rooms in the hotel. And the elevator went down for the weekend, and Joe the bellman actually decided he was going to work sixteen hours a day on Saturday and Sunday on his days off in order to address the fact that you have a seven-story building with no elevator and therefore you need to help the guests with their luggage up and down.

Well, that was the same weekend that he had family in town from New York, so he didn’t really get to see them. Now, of course he got paid double time because he was working sixteen-hour shifts two days in a row, but what he really appreciated was that by Tuesday right after that weekend, he got a call—he actually didn’t get a call, he actually had our head of IT for the company went to his hotel and just sought him out and just said thank you and said, “Listen, at our executive committee meeting we talked about you because the head of operations in the company brought it up.” So the fact—Joe actually felt like “Wow, truly you noticed? You noticed?”

So three key things came out of this new thing we did every week at the executive committee meeting. Number one is we were recognizing people around the organization and they started feeling good about it and because of that, ultimately each of the general managers of our hotels actually started doing it within their hotels. Secondly, the fact we ended our two-hour meeting of the senior leaders on a positive note about some great things that are actually happening in the company, is exactly what we really needed to feel in terms of the feeling of solidarity and the sense of you know what, as difficult as the times are, these good things are happening out there. Finally, the fact that it was actually not the head of operations who would oversee the hotel team who would go and say thank you to that Joe the bellman, it was actually someone from a different department. So it was the head of IT, or it could have been the head of marketing, or it could have been the head of HR, anybody from a different department because what it did is it actually created a cross-departmental relationship that helped that bellman say, “You know, the head of IT is not a geek, he’s a good guy.”

So that’s a great example that didn’t take any money. It just took a little bit of time and a little bit of dedication to celebrating people who are doing just common-day heroism in the field. And that’s to me what great companies do is they become first-class noticers. They notice not just when someone’s doing something wrong and how a manager has to tell you that you did something wrong and write you up. Yes, that is necessary sometimes, but that’s frankly how a lot of managers think their whole job is about writing people up and finding things that are wrong. It’s actually quite the opposite. It’s to find the people doing things right, make sure they know that they were recognized for it, and help them feel like the work that they do is important.

TS: That’s great, it’s very practical and very doable. Now Chip, when you were describing the Modern Elder Academy and this education at midlife, you talked about something called the “midlife edit,” and I’d never heard that phrase before, and of course you’re referring to things we have to let go of that no longer serve us. But [it’s] interesting, in reading about your life in Baja and the Modern Elder Academy, I learned that you picked up something new. You picked up surfing as someone in their late 50s and I thought it’s not just about editing, it’s also about the new things we can add into our lives and that sometimes people think “Oh, well you know, whatever, I’m too old for that, I’m certainly too old to try to stand up on a surfboard—

CC: Tami, you could do it. You’ve done it I’m sure.

TS: Well you know, I’ve gone surfing, it was a little bit of a disaster. I think it was a lesson in humility for sure. Standing up has not that easy.

CC: No, it’s not that easy. So, a couple thoughts here. One is I’m a big believer that that first half of our life is about accumulating and then we have this new curve of happiness and around 45 to 50 or early 50s, people sort of hit the bottom of that U-curve of happiness and the way they get out of that is actually to let go of a bunch of things. So if the first half of life is about accumulating, the second half of life is about editing. But editing doesn’t necessarily mean you just make your life smaller. Editing just allows you to get rid of the baggage that you’re carrying during this midlife marathon that used to be 45 to 65 and now is 35 to 75.

So one of the other key concepts we pose is something that comes from Carol Dweck from Stanford, a psychologist, called Mindset. She wrote a landmark book a few years ago called Mindset and was able to outline that there’s two kinds of mindsets—and they’re not binary, people sort of on the spectrum relatively of these mindsets. You either have a fixed mindset or a growth mindset. If you have a fixed mindset, you have a tendency to want to prove yourself. So you tend to focus on things that you can win. So success is defined by winning and that means you frankly operate in a relatively small sandbox, and especially as you get older, maybe the sandbox gets smaller because you don’t want to pick up Spanish as I’ve been doing in my late 50s because you’re going to look awkward. You’re going to look liminal—you know, that word I used earlier.

Liminality is something that many of us think is like, that’s just puberty. To be in transition and to be awkward is just something that you have in puberty—but actually you have it in your whole life. There’s a great TED Talk by Dan Gilbert about how he was able to show every single age range, every single decade of your life, people massively underestimate how much change is ahead of them in their next 10 years. So that’s the fixed mindset, is you’re proving yourself. The growth mindset means you’re improving yourself. And so winning is not—success is not winning but success is learning.

So the thing that we help people to see is that if you are 58 years old and you’re going to live until 98—which for many people, there’s a moderate probability of that. At age 58, you are only halfway through your adult life if you start counting at age 18. So the questions we need to start asking ourselves are questions like this: what is it that I know now that I wish I had known 10 years ago? And that’s a really interesting and provocative question, come up with your list. Then ask yourself based upon that thinking, what is it 10 years from now I wish I’d learned now?

10 years from now I wish . . . I live in Mexico half the time. I learned French, hence the name Joie de Vivre for my company, when I was growing up. I did not learn Spanish, so in my late 50s I’m learning Spanish. Now people would just say, “Oh, isn’t it hard to learn Spanish or surfing at that age?” And the answer is yes, it’s harder than it would have been 10 or 20 years ago, but if I plan to live in Mexico half the time and I don’t understand Spanish, I promise you I’m going to be more regretful 10 years from now if I didn’t give it the attention now.

So it’s really just sort of a seize the day perspective and an openness to looking awkward and to realize that to get into that sort of Mihaly Csikszentmihalyi flow channel where you’re able to be using your challenge to build skill, you need to be open to trying things that are new. And over the course of a week at the academy people learn—if they choose to, they can learn how to surf, they can actually bake bread in a collaborative group. If they’ve never had any experience with yoga or meditation, they will be learning that. And a whole collection of other things.

So yes, I think it’s really important. One of my favorite modern elders of all time before the term existed was Peter Drucker who lived until his mid-90s, he wrote I guess two thirds of his 40 books after the age of 65 and every 2 years he would go study a new subject that had nothing to do with being a management theorist and author. It was everything from Japanese Ikebana flower arranging to medieval war strategies, and what he felt was that he wanted to lubricate his heart and his soul and his mind by being fresh and a beginner’s mind at something new.

TS: Now Chip, I want to ask you a question about this idea that you proposed that the first half of our life is about accumulating and the second half about editing, what would you say to that person who’s at midlife and says “Look, I’m not done accumulating. I don’t have the savings that I need, I’m not ready for the editing phase.”

CC: Yes. So, let me say the accumulating I’m talking about is across all levels. It doesn’t necessarily mean accumulating money exclusively, it could be accumulating responsibilities, knowledge in certain areas, et cetera. If there’s things you want to continue to accumulate—like the example I just used with Drucker, Drucker wanted to accumulate learning new things. So I’m not saying you shouldn’t accumulate certain things that are important to you. But what you can see over the course of a person’s 20s, 30s, and 40s, often they have accumulated without editing. Without sort of saying, “I’m now going to discard that.” And I’m not saying discarding your husband, wife, whomever, which is the classic midlife crisis. No, I’m saying discard the things that aren’t serving you and that don’t feel like they are providing fuel for you for the second half of your life. Yes, it could be relationships, and in terms of the financial world, 41 percent of Americans 55 and older do not have any retirement savings.

So let’s be clear, accumulating some savings and some money is an essential piece of life and just listening to this guru Chip talk about stop accumulating, I’m not talking about stop accumulating money when you need it. But in order to fill a glass, sometimes you actually have to pour something out in order to add something new. And that’s really what I’m saying. Sometimes it’s the thing that holds you back from trying something new is the fact that you’re juggling a bunch of other things at the same time.

TS: Now you mentioned, Chip, that part of your background experience that lead to the founding of the Modern Elder Academy had to do with you working with young founders or Airbnb as their strategic advisor. What was it like to you to come in, several decades older than these young founders and be the strategic advisor, the old guy on the scene?

CC: So initially it wasn’t even the strategic advisor. Initially it was, I was the head of global hospitality and strategy, so I was a full-time employee reporting to someone 21 years younger than me, Brian, after having been CEO of my own company for 24 years. So that was a bit of a shock, and the reason I did it was I was really fond of Brian. I could see how voracious his appetite was to learn. And unlike some Silicon Valley entrepreneurs, he was pretty humble about what he didn’t know and what he wanted to learn and he really wanted me to be his mentor.

But what I came to learn pretty quickly was that we were mutual mentors. I learned as much from him as he did from me. I probably taught him a few things about EQ and leadership and things like that and strategy et cetera, but he taught me a ton about DQ, digital intelligence, in terms of understanding not just how to use my iPhone with all of its uses, but literally how do you create a website, what is product? I didn’t even know what the word “product” meant in terms of product being the software application and just truly the website.

So I learned a lot about that. I learned about Silicon Valley investors. I had my own company but I didn’t have tech investors in my company, I was a hotelier. So, I learned as much from him as he did from me and I think that the four stages that I had to go through to become a modern elder, so to speak, which is what they started to call me, is I had to evolve. My first step was I just had to evolve, which meant really letting go of things. I had to let go of, I was not CEO of this company, so I had to right-size my ego. I needed to know that most of my hotel knowledge wasn’t all that valuable in the home-sharing world. So, I had to start with the evolution to let some stuff go, to edit.

And then secondly, the second lesson was to learn. And I cover all of this in my book Wisdom at Work: The Making of a Modern Elder. Learn was the second piece which is like, OK, learn something new. I had to learn tech. I had to learn all the lingo of tech, I had to learn the lingo of Millennials. I had some familiarity with that, but frankly working every day, day to day, next to people who were half my age was really fascinating. The third lesson was to collaborate, which is where you start moving into the lessons that if you’re older you might have some advantage in; our EQ does grow with age, and there’s a ton of evidence now that age-diverse teams are very effective and they’re partly effective because you have older people on a team, they help create some emotional moderation for the team. And then the fourth lesson was counsel. So, evolve, learn, collaborate, counsel.

What’s interesting and what I think has led to the “OK, boomer” phenomena is some older people go straight to counsel. They think that their job is to just advise young people and tell young people how the world works and lament the fact that young people aren’t respectful or et cetera, et cetera, et cetera. And what they get out of that is “OK, boomer.” So I think counsel is the thing you earn once you’ve done those other three things first because people then notice you, young people notice you and say “You know, I’d like to go talk to Chip and spend more time with him.” And 75 percent of Millennials would like to have a mentor and only about 2 percent say they actually have an official mentor in their life. So, there’s a real gap there and a real opportunity, and again, if you’re the mentor as the older people, do know that you’re probably going to learn as much from that younger person as they will learn from you.

TS: On your second point, “learn,” one thing I discovered in reading about you Chip in advance of this conversation was that every Friday—in your whole life, your whole entire life, your whole life, your whole adult life—you’ve written down what you learned during the week. And I thought that was just remarkable. How did you start doing that practice?

CC: It’s a discipline, huh? We all have disciplines in our life: we shower and we brush our teeth and things like that. So this was my weekly brushing of the vocational teeth in the sense that at the end of the week, once I started my company at age 26, I, on Friday afternoon or often on Saturday or Sunday, I would sit down with my wisdom book. And it was just called the wisdom book, and I have many of them now because I’ve run through so many books. And this wisdom book, which is just like a diary of my own, was just a listing of almost like bullet points. It was not exactly a journal, it was more like bullet points of, here’s my key lessons of the week.

So that journal of learning, that wisdom book, was frankly much more powerful during the difficult times because when I was going through difficult times, I was trying to make sense of that. Viktor Frankl’s book Man’s Search for Meaning led me to writing a book called Emotional Equations, and the first equation in that book is despair=suffering-meaning. And if you have bit of a Buddhist proclivity you know that the First Noble Truth of Buddhism is life is basically about suffering, learning that that’s just part of life. And therefore if that’s the constant in life, the variables in this equation of algebra is despair and meaning. And despair and meaning are inversely proportional to each other. If you do the math exercise here, if 8=10-2 and 8 is despair and 2 is meaning, if you can move the meaning up to a 6 then despair moves down to 4. 4=10-6.

So what I learned is if I focus on what I’m learning, especially during the times when I’m most troubled, I will be in the process of developing, cultivating, and harvesting wisdom along the way that I can use in the future. And where that was particularly prevalent for me was during the great recession. I had a flatline experience, I died after giving a speech on stage—for all kinds of reasons I can explain later but it was not a heart attack, but it was my heart stopped. And luckily the paramedics were there; I had gone unconscious first and my heart kept stopping. And that was really when I realized how much I didn’t want to be doing the life I was doing at that point, to the point it literally felt like it was the proverbial wake-up call for the hotelier who didn’t want to be a hotelier anymore. And I found during that period of time—during the two years from that flatline experience to when I sold the company, which was a difficult era during the depths of the great recession—that my opportunity every weekend to make a list of what I learned that week was the thing I looked forward to during a really treacherously difficult week each week. Because I could feel like “OK, there’s some purpose, there’s some meaning. There’s not just despair here, there’s actually some meaning.”

So yes, I highly recommend it, for anybody especially who’s going through a difficult time. So what an example of what I’d write down is like OK, we had an investor in a hotel that had a completely different definition of success than we did, and it made me realize that early on when I build new relationships with investors in a hotel, I want to actually have a conversation with them. When I’m interviewing them, not just them interviewing me to potentially invest into a project, but when I’m interviewing them to see if they’re the right kind of investor, I’m going to ask the question of how do you define success, especially in difficult times? Because what happens often in many businesses is in the difficult times, you see the investors show their stripes and they have a tendency to say “Let’s cut, cut, cut, cut, cut,” when all that cutting hurts the culture, hurts the long-term relationship with customers, et cetera. And I’m not saying you shouldn’t do some cutting, you absolutely have to, but yes.

TS: It’s always interesting me to me the practices that people develop on their own that are their lifelines or their own adaptations that end up being so important to them, so interesting.

CC: But I’m sure you have your collection of them.

TS: I do, I shared about tuning into the inner fountain which is one of my secret practices, I have a few more and I’m not ready to share them today. But I am curious, so you had a full-on near-death experience and it sounds like—

CC: Yes, I went to other side. So I came back from the other side, told the paramedic what I’d seen, and then by the time I was in the hospital I’d done it a few more times and then I kept telling the nurse in the emergency room what I was seeing, and every time I was seeing the same thing.

TS: And . . .

CC: It was weird. Do you want me to tell you what it was?

TS: Of course! I’m on the edge of my seat.

CC: OK. Actually interestingly enough when I was doing the festival thing, I found out that there’s a festival of the near-death experience. It’s actually called the Pilgrimage of the Near-Death Experience in northwestern Spain, so I’m going to go there someday.

So what I saw interestingly enough, especially considering you’re in a mountain area and I’m a beach kind of guy, my experience being on the other side was in a mountain chalet—which is I’m not a mountain kind of person so much, but it was in a mountain chalet, very high elevation. There was a skylight in the—so light was cascading into this living room and so much so that there was a kaleidoscope of colors on the wall like a rainbow and I was just observing this like I was sort of like an angel in the air watching it. And there was this viscous frangipani tropically scented oil that was actually on this spectacularly beautiful wooden floor that was dripping down this wooden staircase extremely slowly, like you know, Heinz 57 sauce or ketchup-like anticipation.

And everything was moving slowly but everything was completely abundantly beautiful. There were no people there but light. I just saw just this effervescent light that was coming in that made everything look sort of sparkly, I guess. So I’d come to and I’d tell the people, “This is what I just saw,” and they said, “Well that’s what you said last time.” It’s like wow, OK, that’s interesting,

I’ve never really had anybody professionally tell me, here’s the meaning of that, other than to say I think what I got more than anything was two things. One is just the importance of beauty. Just beauty and aesthetics are—later in Maslow’s life, he added aesthetics and beauty as a higher level above self-actualization, before he had the level called transcendence, I think. So I think aesthetics and beauty was an essential piece of it. The other thing I think was the sense that the oil was going down the staircase very slowly. It was almost a sense of OK, at a time where all around me I know there’s hypervigilance of craziness around me trying to see what’s wrong with me and et cetera, if I had some awareness of that. But what I was feeling inside was the sense that time was moving extremely slowly.

TS: Well the thing that I’m curious about, Chip, is, how did it feel to you when you were observing this vision, what was the feeling like?

CC: It felt completely timeless. I was typically out, according to—I’d never heard of the word “asystolic,” which basically means you don’t have a heartbeat; I’d never heard it. When I would come to, they would say “He’s asystolic, he’s asystolic,” but when I asked later how long was I asystolic, it’s like, 10 seconds, 20 seconds, not long. But it felt like days. So the feeling was just complete contentment and no sense of having a clock. In many ways, one of my gods in life has been efficiency, and I don’t know if you’re the same way, Tami, but—

TS: No.

CC: No? [Laughs]

TS: No.

CC: OK, you’re not. So efficiency has been—and I’ve gotten a shitload done in my life partly because I have been pretty efficient with how I do things. Now I love artistry, I love all kinds of things, so just being efficient is not the only thing I do, but you spend time with Chip in whatever environment I’m in, people get used to like “OK, Chip runs his meetings on time,” et cetera. What I felt when I was on the other side was how little time mattered. How little this god of efficiency was relevant at the end of the day. I think in many ways it prepared me for why I live in rural Mexico now, which is a place where people have fiestas and siestas all the time and you have a sense of a little bit more spaciousness in life.

So for me, one of the things that I’m really focused on, I have a new daily blog I write called Wisdom Well and it’s a daily blog and I just wrote a blog this morning that’s going to go live pretty soon, in the next few days, and it was just about the difference between a to-do list versus the to-be list. I’ve spent my life being exceptionally good at finishing my to-do lists which is my god of efficiency, but the to-be list is to be spacious. What are the habits and practices in my life that allow me to be spacious? Because what I felt when I was on the other side and supposedly dead at that moment, or at least with no heartbeat; I wasn’t dead I’m still living today. But I felt the sense of spaciousness that I feel when I’m in Mexico, which is part of the reason I moved out of San Francisco.

TS: And your decision to sell Joie de Vivre came after this flatline experience?

CC: Yes. That’s what accelerated my process of saying—I thought I was going to do this my whole life. Like you, Tami, it’s like I thought I—I started when I was 26, I said in my own head, “I’m going to do this 50 years. So at about 76, I will . . .” and I didn’t ever think I’d sell, I thought I would like, find somebody within the company and do an ESOP so the employees owned it and move forward. So basically halfway through that 50-year period, 24 years into it is when I sold, and 22 years into it is when I had this experience, the flatline experience. And what I realized is, you know, I had five friends commit suicide during the great recession—

TS: Oh my.

CC: But one of them was named Chip. So here I had this weird name Chip and one of my close friends is named Chip. And it’s like OK, it’s just funny, two Chips to start with. And this Chip, who was my insurance broker, was a spiritually deep person, which you wouldn’t expect from an insurance broker typically. When I was going through—early part of 2008, I was going through some difficult times. I could see this recession coming and I knew I didn’t want to do this hotel thing anymore after all these years, and it was sort of sneaking up on me, what had been a calling was now a job. And Chip helped me through that, and then about a month after that conversation, he committed suicide. And it really rocked me, especially going to the memorial service for him and everybody was telling their Chip stories. And I had been, frankly, not quite suicidal but certainly close to it, thinking like the only way I can get rid of my identity was to actually have an accident or something terrible had to happen to me because I felt so wedded to the identity of being the founder and CEO of this company.

Weirdly, a couple months after Chip passed away and I’d been going through my, “OK what does Chip’s passing mean to me,” I broke my ankle playing baseball, I got a bacterial infection in my leg and was on a strong antibiotic that led to an allergic reaction, and that’s why I had my flatline experience. And it was this sense of divine intervention of like “OK, I’m listening now. My body is talking to me, I’m listening. I’m going to do the thing I didn’t think I was going to do.” So it’s something, it’s so hard. You know; you know better than I do.

TS: Yes. I think one of the big questions that comes up for me in thinking about modern elders at work is, is it possible to stay in the workforce—so this idea of when are you going to retire, when are you going to sell your company? No, I want to stay a strong contributory presence and give my gifts. I’ve finally figured out some moves that work and how to stay centered and be in my heart, I’m finally getting the hang of it. Why would I leave now? However, when you talk about the to-be list as well as the to-do list and this increased reverence for spending time in nature and being in beauty, I want that too. And I think if we can design our businesses differently and have older people partner with younger people, perhaps that’s possible. Perhaps it can be a both/and.

CC: Oh that’s the future. We need a new generational compact. We have five generations in the workplace for the first time and each of us have something to bring to the table and it’s like an intergenerational potluck. Whether it’s addressing the biggest problems of our society or it’s just even the problems in a company, singular company. So big believer in that; also big believer in the idea that as we get older we sort of move into more of a service function. We’re here to serve others, and for sure—technically, I think that’s really what we do anyways, but I think it’s even more evident later in life that we’re here to help support people who are younger than us microwave their skills.

TS: OK and just the final note I want to talk about, Chip, and this is a personal thing but I wouldn’t be true to myself if I didn’t talk about it. Which does bring up something else, which is, being true to oneself, I think that’s a value you and I both really share. And I wanted to ask you, what has been the biggest risk you’ve had to take to be true to yourself in your life? Where did you have to walk out on the limb the furthest?

CC: I think I had to walk out 33 years ago when I started my company as an out, gay CEO. Fortunately, I was in San Francisco and fortunately I was one of the first boutique hoteliers in the US, so I was going into an industry and sort of a pioneering piece of it, design-oriented hotels, where being gay was not as big of a deal. But being a gay CEO was a big deal and we had hotel—so I owned Joie de Vivre the company by myself, but we had 52 boutique hotels so we had many hotels that we owned with other people, or we managed hotels or created hotels for owners that we didn’t own and we were the brand and the management company.

So I had so many times when I had awkward moments with people who wanted to be investors or were investors where in the process of vetting each other, of course I would tell them that I’m gay. And I remember at least two or three times when I had very Christian, conservative investors in one particular hotel that we did end up doing a business together, but I looked in their eyes when I told them I was gay because they were asking me about my wife and I just saw this blank look.

Again, today it might not be as big of a deal, but 33 years ago or 27 years ago when I think this particular incident happened, it was a huge deal. I mean, these folks were from rural Arizona and they couldn’t believe that I was an out, gay man. As they said to me like five minutes later after they caught their breath and went to the bathroom, he said “But you don’t act gay.” [Laughs] And I said, “Well, what does that mean? ” And he said, “Well, you’re decisive and blah blah blah.” I said, “You know, the bottom line is this.” When I came out at age 22, I was able to tap into skills I had in certain areas that I was embarrassed about. I had a good design eye, I was empathetic, I understood the other, what it means to be the other in a situation, even as a white male because I’d gone to high school in the inner city so I was called the “curious white boy” back then. but I had capacities that I didn’t have to hide because I was being true to my sexual orientation.

And I’ve got to tell you, over the course of the next five or six years with him as my partner—him and his son as my partner, it was an older man—I saw him occasionally just give me a smile and say, “You’re being true to yourself” after a meeting. And I loved it. It had nothing to do with my sexuality but what he said was, “You know what, you ran that meeting really well. You listened really well. You had some great creative ideas, you’re being true to yourself.” And I knew—he never said the orientation thing again, but I knew it went back to that conversation we had.

TS: Yes, you know I think at this point in 2020, I don’t think anymore so much about the risks it took back in the mid-1980s to be out and proud, leading a company and raising money, I don’t think about that so much anymore.

CC: Yes, fortunately. We’re lucky.

TS: OK, now here’s the question I want to ask you, Chip. It’s something that I don’t have a good answer for in my own experience, which is why I want to ask you. You’ve created so much, you’re such a pioneering person and your projects have such a positive influence on the culture. How do you know when you’re creating and your ego’s involved in some way, and when you’re creating and it’s just really pure and in the flow and there’s no ego contamination? In my own life I often find there’s some combination of both, truth be told, and it’s hard for me to sort it, especially when a new project is coming on. And I’m wondering how you sort that?

CC: That’s a great question. I think on a day-to-day basis I have to sort of just check the ego, but when I’m looking at bigger decisions that I’m making, I really look at, would I be OK with not having any credit attached to this thing we’re doing? So for example, I’ve been giving philanthropically for a long time but I’ve started doing a lot more philanthropic giving anonymously. And it’s been interesting because anonymous donations really don’t have a lot of ego involved, unless it’s your own personal ego feeling like you’re even a better person because you’re anonymous. But the reason I’ve done it is generally because it’s been an anonymous match, so what I want to do is put a match out there and anybody who gives a dollar I match a dollar and I don’t want them to feel like, I don’t want my involvement to—I just want it to be anonymous. I want them to know that there’s an angel out there doing that. So when I’m doing something like that, it feels really pure because it feels like I’m not trying to get any credit for it and I know it’s having a great effect.

But if we’re launching something—at Airbnb I had to be really comfortable with the idea after having been the “sage on the stage” of my own company to be the “guide on the side” and to know that gosh, in the first few years of Airbnb me being there, I didn’t get a lot of attention. People in the hospitality industry knew that Chip was the guy behind the scenes with Brian and the in-house mentor, but I wasn’t getting much attention. I actually got to a place where I realized you know, I’ve gone from trying to be interesting to being interested. And that shift of moving from interesting to interested is sort of the classic shift of, in midlife when you move from your primary operating system being your ego to your primary operating system being your soul and when you make that shift, something eases up in your whole somatic system, your body and your energy because in some ways you’re serving someone else more than serving your own sense of accomplishment or fame.

TS: A beautiful answer. I want to come down to Baja and go surfing with you, Chip.

CC: I’d love it, yes! Come on down. You know it’s so funny, your voice reminds me so much of my friend Liz Lambert, if you know who Liz is.

TS: I don’t, no.

CC: She started Bunkhouse Hotels, she’s based in Austin and she lives at the other end of the beach from me. But you know, come on down—and another lovely lesbian who, I helped her get into the hotel business 20 years ago, so you guys have very similar voices. I love what you’re doing, Tami, thank you for what you do and thanks for having me on your show.

TS: Thank you so much. Chip Conley, he’s started Modern Elder Academy in Baja and also written the book Wisdom at Work: The Making of a Modern Elder, and he’ll be a presenter in the new Inner MBA that Sounds True is producing along with Wisdom 2.0, LinkedIn, and NYU. Graduates of the nine-month immersion program receive a certificate of completion from NYU and if you’re interested in learning more about the program it begins in September of 2020, you can visit

Thank you for listening to Insights at the Edge. You can read a full transcript of today’s interview at and if you’re interested, hit the subscribe button in your podcast app. And also if you feel inspired, head to iTunes and give Insights at the Edge a review. I love getting your feedback, being in connection with you, and learning how we can continue to evolve and improve our program. Working together, I believe we can create a kinder and wiser world. waking up the world.

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