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Podcast 306

306: Sharing Your Wisdom in Your Second Act with Chip Conley

Today, I’m talking to Chip Conley. Chip founded Joie de Vivre Hospitality at the age of 26, turned it into the second largest boutique hotel brand in America, and sold the business 24 years later. Soon after, the founders of Airbnb came to him for advice, and he joined them as their Head of Global Hospitality and Strategy before settling into a role as their Strategic Advisor for Hospitality and Leadership.

He’s also the founder of Modern Elder Academy, the world’s first “midlife wisdom school,” with a campus in Baja California Sur and one soon to open in Santa Fe. In his most recent book, Wisdom at Work: The Making of a Modern Elder, Chip writes about the value of humility, emotional intelligence, and wisdom–and how companies like Airbnb benefit from skills that can only come with age.

In this conversation, Chip and I discuss the identity crises that come with exits of all sizes and the lessons he learned by joining Airbnb, how our calling evolves over the course of our lives, and how to find (and take advantage of) the incredible opportunities that life transitions give us.


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In this podcast interview, you’ll learn:
  • What it means to be a modern elder.
  • The difference between calling, purpose, and meaning.
  • How Chip is working to teach wisdom at Modern Elder Academy.
  • What midlife is and isn’t–and why Chip believes “midlife crisis” to be a misnomer.
  • The equations that can help us identify (and learn from) our emotions.
  • Chip’s advice for anyone over the age of 50 who’s thinking about taking a big leap.
Inspiring Quote
  • "The meaning of your life is to find your gift. The purpose of your life is to give it away." - Pablo Picasso
  • "Despair and meaning are inversely proportional. The more meaning you have in your life, the less despair you have, even in difficult times." - Chip Conley
Interview Resources
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Read the Transcript

Casey Weade: Chip, welcome to the podcast.

Chip Conley: Oh, my gosh, Casey, you were made for this. You’re really good.

Casey Weade: Well, Chip, I’m excited to have you here. Thank you so much for that. Well, you have quite the story and quite the history. And I have no shortage of notes here with me today, and I’m not even sure which way to take this. I got to say, I got into things. I said, “Oh, my gosh, this is going to be a great guest.” I started diving in deeper. I said, “Oh, I’m going to be able to figure this out real smoothly.” And then a few hours before we started the interview, I go, “Oh, boy, where do I begin?” There’s a lot going on here. Chip has quite a robust history.

Chip Conley: That could be good or bad. I don’t know how to take that, but generally, you know what? I believe that wisdom is all about metabolizing your experience. And so, I’ve had a lot of experience. The question is, how do you metabolize? How do you digest it? How do you learn from it in such a way that that experience becomes wisdom? And fortunately, I have had enough experience– some of the good raw materials to create a life that feels a bit like a feast. So, I feel very lucky.

Casey Weade: Well, I would say that’s definitely the truth. And I don’t know if you know this, but I wrote a book Job Optional a few years ago and I can tell you are truly living that job optional lifestyle. And you did it in your early 50s. At age 52, you sold a hospitality brand. I’ll probably butcher this, but Joie de Vivre.

Chip Conley: Joie de Vivre.

Casey Weade: Joie de Vivre. Boy, I was darn close to that. Joie de Vivre. So, you sold and exited from Joie de Vivre, had a big exit there. And then you could have just sailed off into the sunset and hung out in the Mexico Baja, which I know you love so much, but instead, you ended up going back to work with Airbnb at that time being what sounds like a mentor really to the founders and really helped turned it into what it is today, a household name. What made you decide to do that?

I mean, people have these big exits, and this can be a really confusing and stressful time when we go through this big exit. Maybe we have an identity crisis, maybe we decide we’re going to go into retirement, and then some just don’t know what to do next. What led you to go back to work when, I think most would probably say, Oh, I made it, I’m done, I’m going to go relax?

Chip Conley: Casey, do you remember the movie The Intern with Robert De Niro and Anne Hathaway? Did you ever see that?

Casey Weade: Yes, I mean, it was a long time ago. Yes.

Chip Conley: It’s a fun movie. And De Niro was 70 years old in the film. And early in the film, he says musicians don’t retire. They quit when there’s no more music left inside of them. So, I had sold my company that I ran for 24 years as the CEO, and Joie de Vivre became the second largest boutique hotel company in the US. It’s now a Hyatt brand.

And I knew that I had music left inside of me. I wasn’t really ready for retirement, but I wasn’t really sure who to share that music with. And then one day, I got a call from a guy named Brian Chesky. I didn’t know him at all. Brian Chesky was one of the co-founders of Airbnb, young guy. I was 52, he was 31, and he said, “I’d like to come over to your house and talk with you about you becoming my mentor and you sort of coming in-house for our little company.”

And I said, “Well, I didn’t know much about Airbnb.” I know the hotel industry, thought it was a really terrible idea. And I said, “Come on over to my house.” And he did. And this is all in San Francisco. And he said, “I’ll Uber over to your house.” This was 10 years ago. And I never heard of Uber, even though Uber was a San Francisco company, but I’d never used Uber. And he said he was Ubering over to my house. I have no idea what that means, but yeah, come on over.

And we spent an afternoon together and I saw a really curious, smart, idealistic young man who had an idea that was just take it off, but he had nobody. It was a small company and nobody in the company with any hospitality or travel industry background. Very few people in the company that ever run a business before or started a business.

And so, I joined as the head of global hospitality and strategy of the company, definitely way older, twice the age of the average employee in the company. But the main thing was I was there to be Brian’s mentor, and about a month or two into it, he said to me, “Chip, we hired you for your knowledge, but what we really got was your wisdom. You are our modern elder.” It was like, I don’t want to be a modern elder. That sounds like over the hill. What is the modern elder?

And he said, “No, you’re not elderly. A modern elder is someone who’s as curious as they are wise.” I was like, “Okay, I’ll take that.” Curiosity and wisdom are both qualities that I hope people see in me. And from that point forward, I was known as Airbnb’s Modern Elder and spent seven and a half years with the company taking it to where it is today. It is now by far the most valuable hospitality company in the world. At one point, it was worth $120 billion.

The stock market’s recent craziness has actually dropped that, but still, at one point, it was worth more than the five largest hotel companies in the world – Hilton, Marriott, Intercontinental, Hyatt, and what am I forgetting? One other one, and Four Seasons, actually. And so, it’s bigger than all five combined. So, it’s been a fascinating run. And yeah, it taught me a lot about what does it mean to be a mentor.

Casey Weade: When you had that exit. I’m curious, did you know that you had music inside you at that point? Or was there a point of disillusion there that you weren’t really sure? What was that?

Chip Conley: Yeah, I did know that. I mean, it was interesting, Casey. I left, I decided to sell my company at the bottom of the Great Recession. It was not the best time. It was a good exit for sure, I did find financially, but if I’d waited three or four more years, I would have done a lot better. But I had gotten to a point, after 24 years of running this company, that I didn’t want to do it anymore.

And I actually saw myself as potentially a liability for the company. We had gone from one person, me, to 3,500 people in the company. And I went to Stanford Business School. So, I had some background in knowing business, but I started the company when I was 26. So, I sold it when I was 50, and I was, at that point, I don’t want to say I was having my midlife crisis, but it was definitely having a sense that the thing that had been my calling had become a job, and I didn’t really enjoy it anymore.

So, yes, the answer is I did know that I’d learned some things along the way. I knew I didn’t necessarily want to do the same thing I was doing before. I liked the idea of helping someone else with their business, and it did mean that I went from being the sage on the stage, sort of the frontman, the person, the brand of my company was sort of synonymous with the brand of chip. And all of a sudden, I became the guide on the side, not the sage on the stage. I was the person helping to guide these young co-founders in their company.

And I wasn’t getting a lot of accolades, so I had to right-size my ego a little bit, I will tell you that. And that was good. It was really helpful. And I ultimately saw that I was a can-do-it. I was the can-do-it person forever. Like I can do it, I can do it. And my team, as you ought to be, was full of can-do-it people. But then at Airbnb, I moved from being the can-do-it person to the can-do-it. What does that mean? It just means that I was more the channel for wisdom and for smart thinking, hopefully, for these younger people who had a great idea for a business but didn’t necessarily know how to execute it.

Casey Weade: Well, yeah. Then that really hits home for me. I hired a COO here, brought in a new COO about a year ago, and he is in his mid-50s and had his own exits over time, ran very large companies in the past. And that’s where I see him. For me, he is my mentor in a lot of ways. The COO to the CEO, he’s that person that we really need to help guide from a place of wisdom.

Now, you wrote down and you’ve called yourself an intern, and I go, that title that you had to Airbnb doesn’t sound like an intern title. What made you get that sense?

Chip Conley: Well, actually, I called myself the mentor and I was a mentor and an intern at the same time. So, mentoring is someone who is actually both the wisdom keeper or the person who has something to offer as a mentor and then the wisdom seeker as the intern. The reason I say that I was a mentern was because at age 52, I joined a tech company for the first time. So, I’d never worked in the tech world. I mean, that was a brick-and-mortar boutique hotelier. We created 52 boutique hotels, all of them in California.

And so, the idea of working for a company and having it be a tech company was new to me, so I had to learn all of that, I had to learn the lingo. I was surrounded by millennials, 90% of the company was millennials, so I had to really understand millennial lingo, too. So, not just tech lingo, but millennial lingo. I also had to understand venture capital. As a hotelier, I never sought out venture capital because venture capitalists don’t usually invest in hotels. So, that was new for me, learning millennial travel habits, because when I joined the company, almost all of our customers were millennials.

We had a lot of hosts. So, our guests were mostly millennials. We had hosts of all different ages. And our fastest growing set of hosts after I joined was boomers and older Gen Xers. And that was partly because they had space, they had the space to rent out to people. So, long story short is I just realized that I needed to be curious, I needed to be a learner as much as I was a teacher.

Casey Weade: Yeah, that’s so key for anyone that’s going to enter that role. And I wanted to take the conversation in a way of talking about the differences and the benefits of the pros and cons of having younger workers versus mid-career workers. But I think you’ve nailed it there, and I think it has a lot to do with exactly what you said about curiosity and calling is where I really wanted to take this because you have said you have multiple callings throughout life. We all have multiple callings throughout life, but I want to define calling first. How do you delineate, and maybe you don’t, between calling and purpose? What’s the difference between calling, purpose, meaning? Do those things mean something different to you?

Chip Conley: I love it. I love it, Casey. You ask good questions. Well, first of all, I think there are three kinds of relationships we can have with our work. It’s either a job, a career, or a colleague. And I would put it in the form of a pyramid. One of the books I wrote was called Peak: How Great Companies Get Their Mojo from Maslow. And in that book, I actually have a pyramid, the employee pyramid, and I say most people have a job. Then as you move up the pyramid, some people have a career, and then a lucky few have a calling.

A calling is often something you have when you feel like it is almost gifted to you. It feels like you’re doing the thing that you’re supposed to be doing on this earth, and it’s natural to you, but it also feels a bit like you were fortunate to be doing it. It feels like there was some divine intervention that allowed you to be in a place to be doing this work. A calling is something that energizes you such that if you had a job and you worked 8 or 10 hours in a day, you might be burned out at the end of the day. If you’re living your calling, you actually are energized by the work. You lose track of time and you’re more pumped up after working than you are when you started the day. So, that’s, I would say, sort of the idea of a calling.

So, let’s talk about meaning and purpose. I’m going to quote someone. It’s unclear who actually said this first, but Chip Conley says it a lot these days. And that is the meaning of your life is to find your gift. The purpose of your life is to give it away. So, let me actually unpack that a little bit. So, meaning to me is a very personal thing. You get meaning because it actually, internally inspires you. You feel a sense of you’re moved by it, something that is meaningful for you is personal, it’s a way we look at the world.

And so, the meaning of your life is to find your gift. So, what does that mean? It means that there are some gifts, some talents, some strengths, some elements of a talent that you have that you need to uncover, it’s inside of you. And for some people, they never find it. It’s a discovery inside of them. And of course, you build the talent. The process of building the talent is really the second piece of this. So, the meaning of life is to find your gift. The work in life is to develop that gift.

And then the purpose of your life is to give it away. So, the way I see meaning, it’s very personal. Purpose is very social. So, what does that mean? Purpose is to give it away means you are being social with the gift. The thing that is the very personal thing to you that you love, that gift, the moment you start to actually give it away, you are giving a social good. You’re actually offering it to other people. And that’s what I’m doing today. We’ll talk about it in a few minutes with being the founder of the Modern Elder Academy.

But in some ways, my time at Airbnb was that as well, the meaning of my life was to develop my gift as an entrepreneur, as a hospitality executive and maverick, and then to build that gift. And then part of my life was to develop that. And then part of my purpose at Airbnb was to give that gift of what I learned my wisdom away. So, the meaning of your life is to find your gift. The work of your life is to develop it. The purpose of your life is to give it away.

And so, I gave it away. I didn’t necessarily give it away, I got paid. And I got lucky enough to earn a lot of stock. But I’m doing the same thing now with the Modern Elder Academy. And I really do believe that when you get to a stage in your life where you take quite seriously development psychologist Eric Erikson’s point of view, which is I am what survives me. Those five words, I am what survives me, speak volumes to being in a place in your life where you want to give that gift away.

Casey Weade: So, would it be fair to say the meaning and the work in developing that gift that you discovered, which is your meaning, and then the purpose in giving it away, really meaning the work in development and purpose, those are all fairly static throughout life. You might call that the thread of life. These things are common and consistent throughout your entire life in a constant work in a lot of ways, but then your calling is the piece that’s going to evolve around these three elements over time. So, let’s talk about that for you. How has your calling evolved throughout your life? And where are we today?

Chip Conley: Yeah, so I’ve had really, I would say, in my work life, three callings. And the first one was to be the founder and CEO of one of the biggest boutique hotel companies in the US. And I think the calling was less about being a big-time CEO as much as it was to build a company that was built on a culture and a sort of leadership philosophy that was quite unique at the time in the mid-1980s when they started the company. And it was based upon sort of conscious capitalism, the idea that we as a company should be focused on our stakeholders, not just our shareholders, but how we’re giving a positive impact in our community, how are our employees feeling like their work creates happiness in their lives, etc.

So, I would just say, and I learned a lot from Herb Kelleher, the co-founder and CEO of Southwest Airlines. So, that was the calling during that period. And I wrote a bunch of books. Four of the five books I’d written were during that era. So, the second year of my calling was to become the modern elder at Airbnb. And this just sort of landed in my lap. The first one was like, I went out and started a company, okay, that didn’t land on my lap, I had to go out and take the initiative.

But in the second one where Airbnb called me, and who knew? I mean, I didn’t think or being frankly, when I first heard Brian’s idea for Airbnb, I was like, oh, I don’t think that’s going to succeed, whatever ideas do you have. But as it turns out, it succeeded in a huge way. I had something to do with that success, but they probably would have been moderately successful without me, but they were more successful maybe with me.

And the fact is, the calling there was to realize, wow, how do I move from my operating system being my ego and being the heroic leader? To me, being this person who was here to sort of support them as their mentors, but also to be, frankly, an operator in the business because I was working full time in the business as well. So, that was my second calling.

And then the third calling is where I am today. My calling today is how do we create the world’s first midlife wisdom school dedicated to people who are often in– well, our average age is 54 of the 2,200 alums we have from 35 countries. We’ve had a handful of people from Indiana. And our campuses in Baja California Sur, about an hour north of Cabo San Lucas, so in Mexico, although we are going to be opening in Santa Fe, New Mexico, a couple of campuses there in the next couple of years.

And how do we create a midlife wisdom school so people can actually reframe their relationship with aging and reimagine how they want to repurpose themselves often in their 40s, 50s, 60s, sometimes in their 70s? And we’ve had people come who are in their 80s as well. So, that’s my current calling because there’s actually some really fascinating social science research on this. Becca Levy at Yale, who has a book that came out last month or last month, meaning April, wrote a book called Breaking the Age Code. And she’s become a friend.

And the book basically shows based upon her research that if you actually move from a negative to a positive perspective on aging, you gain seven and a half years of additional life. Now, that’s fascinating because actually, what she’s been able to show is that if you at age 50 stop smoking, you actually don’t get seven and a half years of additional life. You get like, I don’t know, five or six years. If you start exercising at age 50, you get five years of additional life.

So, just changing your mindset on aging has the effect of giving you more life than either of these other two things that are obvious. And we have lots of public service announcements around stopping smoking and starting exercising. Usually, they’re separate PSAs, public service announcements, but we have so little that helps people to address how to reframe their relationship with aging. So, we are really the first school or academy in the world that’s dedicated to that and to helping people cultivate and harvest their own wisdom.

Casey Weade: You said the first midlife wisdom school. And how do you teach wisdom? I thought wisdom was something to be experienced, something that would come out of experience, something that couldn’t be taught. How do you teach wisdom?

Chip Conley: First of all, Casey, when are you coming down? Yeah, I think you’d enjoy it down here in Baja. Yeah, here’s what I believe. Wisdom is not taught, it’s shared. So, imagine a school in which there’s no PowerPoint presentations. Everybody focuses on learning key facts based upon social science research, and then looking at how to apply it to their own lives. So, there’s 20 people in the workshop approximately, and you have our faculty, but also we have guest faculty who come and teach as well.

And what we do is we help people to see, okay, here are the three pillars of healthy aging, according to Dr. Philip Pizzo at Stanford – purpose, wellness, and community. How do you invest in those? Here’s the research from the Blue Zones, Dan Buettner, who’s a really interesting guy who wrote the Blue Zones, and hopefully, will be teaching at MEA next year. So, we’ll work on what you can learn from the five places in the world that have the greatest longevity. And there are eight or nine qualities of those places.

So, once we learn some of those things or we learn what does it mean to become a mentor and maybe be what I call a mentor capitalist, not a venture capitalist, but a mentor capitalist, be someone who actually helps to mentor people, especially in the business world, amongst entrepreneurs as a way of giving back. So, a lot of this, yes, there are some skills we teach for sure, but more than anything, what we do is ask meaningful questions. And then in the context of a small group of people in dyads, one on one, we answer those questions and then we come back to the big group.

So, let me use an example of a particular question. One of the things that’s really true for people in midlife is if they have a fixed mindset, they have a tendency to see that their sandbox that they’re playing in is getting smaller and smaller because when you have a fixed mindset, you don’t like to try new things. And I think one of the real hallmarks of creating a great life in midlife and beyond is to be open to being a beginner again. So, we spend a week together learning how to become a beginner.

So here’s one of the questions we ask. What is it that you know now or you have done now that you wish you had done or known 10 years ago? So, think about that, and then once you sort of lock that in your brain, ask the following question, what is it that you will regret 10 years from now if you don’t learn it or do it now? Now, that question which I asked myself four and a half years ago when we opened MEA, the Modern Elder Academy, that question led me to learning how to surf at that time, at age 57.

Now, you can say, well, 57 is too old to learn how to surf. But my question in my head was like, I live on a beach in Baja. I live a five-minute drive from a pretty well-known surf break. It’ll be harder for me to learn at 67 than at 57. Why not learn now? Similarly, I learned French in high school, as evidenced by Joie de Vivre. That is the name of my company. I didn’t learn Spanish, but I live in Mexico and I like it here. I live here as my primary residence, although I live in a few other places too, but I live here a lot.

And so, will I regret at 67 that I didn’t learn Spanish at 57? Yeah. Is it hard to learn Spanish at 57? Yeah, but here I am four and a half years later and I learned a lot of Spanish. And I’m not fluent at all, but I am competent to carry on a conversation with my team and I can travel the country and talk. And many of us have a bumper sticker in our head of a mindset that says, oh, I’m terrible at tech or I can’t learn a new language or my best years are behind me. And those kinds of mindsets don’t help you as you get older. And so, part of what we’re helping people to do is to see how do you get rid of those mindsets and how do you replace them with mindsets that actually will be helpful?

Casey Weade: Well, and I love that it doesn’t have to be this big. It can be, well, I want to learn to surf. It doesn’t have to be that, well, I guess I have to quit my job and go start a whole new business or a whole new career or do this or that. It can be these little things, and often, it’s these little tiny tweaks that lead to such a bigger life.

Chip Conley: So true. And a lot of times, people come to MEA, they think I’m coming there because I know I need to find my purpose. And so, that’s the title of your podcast. Let’s talk about that for a moment. Often, they come here thinking, I got to go find my purpose. Everybody else has a purpose, but I don’t have one, as if purpose is a possession. It’s like, I left my purpose in the bathroom at the gas station when I filled up the car. It’s like, purpose is not something you leave in a gas station. Purpose is not necessarily a noun. Yes, you can have a purpose.

But the most important thing to know about purpose is what will give you the sense of purposefulness because you got to do the verb in order to get the noun. You got to act purposefully. And especially if you don’t know what your purpose is, then the most important thing to do is to focus on what are the things you would love to do. What are the things that are meaningful to you? What are the causes or the businesses or the ways of life or occupations that are intriguing to you, that give you sort of a curiosity and a passionate engagement? That’s your purpose may come from being purposeful.

So, start by asking yourself, what could I be purposeful at? And that is interesting because when– there was a woman who was down here not too long ago, actually, two years before the pandemic. She was a really successful corporate attorney and had made a lot of money and done very well, but she said something to me privately, and then she said it to the whole cohort. She said, “I don’t like that the thing that occupies me, my occupation, is something that actually makes me not the kind of human I’d like to be. I would like to be doing work that makes me a better human.” I was like, okay, that is a purposeful statement. I want to be doing work that makes me a better human, that feels like, on that purposeful path, you will find your purpose.

And over the course of the week, what we found as she was talking because one of the exercises we do, which is so weird, people come here thinking, okay, well, it’s all getting about the career. Well, we do bread making together, so there’s collaborative bread making. You learn actually how to make bread each morning. So, there’s a small group. There are 20 people, three or four of them each morning are making bread for everybody else with all kinds of ingredients. And then they have a theme song for unveiling the bread. It’s very fun. We do it at a point in the morning where everybody’s a little hungry.

And so, this woman just said, “Listen, when I was a kid, I loved making mud pies. When I was a teenager, I used to hang out with my mom in the kitchen, making her favorite chocolate cake and banana bread. Today, as a corporate attorney, when I’m stressed out on weekends, I go hang out in the kitchen.” And she said, “It’s just dawned on me. I need to create a bakery. I need to quit being a corporate attorney and I need to actually become a bakery, a pastry chef.” And that’s what she did.

And she was lucky enough to be in a place in her life where she had some optionality. She did not actually have to worry too much about whether she was going to make a lot of money as a pastry chef. As it turns out, obviously, she started doing that. She started the process, writing the business plan during COVID. So, she wasn’t going to actually start the store.

But now, she’s opened the store and it’s opened and she’s loving it and she has quit her job. And that’s what I want to do. That’s, for me, the sense of calling I get from helping other people transform their lives and realize that they have a second act, the third act, or a fourth act inside of them when it comes to their work or that they’re ready to retire, but be in a position in retirement to feel passionate about being a grandfather or a grandmother or a political activist or a marathon runner or a master gardener, whatever it is.

Management theorist Peter Drucker, quite famous guy, he wrote two-thirds of his 40 books after the age of 65. He lived until he was 95. And his whole premise in life was every two years, you study a new topic that has nothing to do with your career, just something that you’re passionate about. And that curiosity is like this fountain of youth, it’s the elixir of life. And so, I help people, or we as a company help people to see it doesn’t necessarily have to be your career where you have all this passion and energy. Your calling may be not related to your work, it may be related to something else, but something else that you feel passionately about, so.

Casey Weade: It reminds me of my wife often recognizing that I’m in the kitchen a lot, especially when I’m stressed out. That is one place that I can just lose complete time. And she’s always telling me, “You need to start a restaurant. You need to start a food truck.” I really love what I do. I don’t know. This could be something that I can do on the side, but I can totally relate to these passions that we have outside of our work that can ultimately be developed into something that becomes at the core of what we’re doing every day, at a core of our being in our life. You’ve talked a lot about life stages here. You’ve mentioned midlife quite often. And I get a little confused about that. I go, “Am I at midlife?” I don’t know. What’s midlife today? Can you...

Chip Conley: How old are you, Casey?

Casey Weade: I am 36.

Chip Conley: Okay.

Casey Weade: So, talk to us about midlife.

Chip Conley: You’re officially in midlife.

Casey Weade: Okay. So, I’m now in midlife, but let’s define that. Talk to us about life stages. How do you view life stages? What is midlife? Is midlife crisis still a thing? Throw that in there, if you will. Let’s just talk about life stages and midlife.

Chip Conley: Okay. So, midlife, historically, was 45 to 65, or some sociologists would say 40 to 60. And in the last 20 years, sociologists have started to say that midlife is starting sooner and going longer. So, it’s a bit of a marathon. So, the reason they say it’s not 45 to 65, they say it’s 35 to 75, because in many industries, people start feeling over the hill in their mid-30s. If you’re a software engineer in Silicon Valley, you’re over the hill in your early 30s, at least that’s how it’s perceived.

Advertising agency, same thing, professional sports, fashion, entertainment, media, etc. A lot of industries, people start feeling old partly because change is happening faster and partly because of the predominance of digital. Seven of the ten most valuable companies in the world today are tech companies. So, every company wants to look like a tech company. And yet, generally speaking, the people who are brilliant with tech are generally younger. So, 35, so you would potentially be in midlife. The reason that now goes longer is because there are more and more people who don’t want to retire at 62 or 65 and they want to continue.

And so, I would say that midlife is less a specific age and more of a stage. It’s a stage of life when you are going through major career advancement, often combined with the complication of a lot of stuff happening at home, often being married, often having kids, often accumulating stuff and responsibilities and obligations. And that is what leads to the midlife crisis.

Now, I don’t love the term midlife crisis, but it is, as a brand, midlife has one word stuck to it. Crisis. Midlife crisis. If this was, what would be? What’s the game? I know there’s a game where, I don’t know. There used to be a TV game where you’d say one word and you say, like have a blank at the end. Like, what word would you say next? 98% of people say midlife crisis.

The thing about midlife crisis that is a little misnomer, my friend Brene Brown, Brene Brown is a famous sociologist and Ted talker and podcaster and amazing author. She calls it not the midlife crisis, she calls it the midlife unraveling, which sounds terrible. But what she means is that there’s a point in midlife, often between age 45 and 50, but your mileage may vary. When you have accumulated so many things going on in your life, then you feel like you’re the circus performer with spinning plates and it’s too much and you just need to actually start saying, okay, I’ve accumulated up to this point in my life. Now, I have to start editing and start determining what’s truly important.

And I like to call it the midlife chrysalis, not crisis. And because I actually think if you think about the journey of the caterpillar, the butterfly, there’s the caterpillar eating leaves, bulking up. And at some point, the caterpillar spins this chrysalis in this cocoon and it goes into it, and then it liquefies, and on the other side of it, it becomes a butterfly. We all know that from third-grade biology. And yet, what’s so interesting is it’s that chrysalis, it’s that midlife chrysalis where you are in the midst of major transformation. And yet, I really don’t think that we as a society have helped people to see that that transformation on the other side of it is the butterfly.

And this is where social science research is really conclusive, which shows it’s called the U-curve of happiness. The U-curve of happiness speaks to the idea that between age 22 and about 45 to 50, our life satisfaction declines. On average, your mileage may vary. And then around 45 or 50, you bottom out in life satisfaction. And in each passing decade after that, you get happier and happier. So, people tend to be happier in their 50s, in their 40s. And I definitely was. Happier in their 60s, in their 50s. And I’m 61 and a half now, so I’m feeling good about that. And then happier in their 70s, in their 60s, and women happier in their 80s, in their 70s.

So, what’s fascinating about that is the societal narrative on aging is if you can make it through your midlife crisis on the other side that you have disease and decay and decrepitude and death. But the personal narrative on aging is quite different than that. Generally speaking, people see that they get happier after about age 50. And so, I highly recommend, and if anybody’s fascinated by this, read my book Wisdom at Work: The Making of a Modern Elder, or come hang out with us at the Modern Elder Academy or do our online course. You can find it all at The online course, we have a purpose course and we have a transitions course. So, I just think we need more people in midlife aware of the fact that there are a bunch of unexpected pleasures of aging, and life actually can get better after age 50.

Casey Weade: Well, it seems like one of the biggest risks would be missing out on the opportunity to just simply recognize that we’re in the metaphorical cocoon, that we are in midlife crisis, that we are on the edge of something very big, very important in our life, and recognizing that if we are in that spot, there are all these amazing opportunities for us to take advantage of, and if we just blindly go through it, we can end up missing out on these massive opportunities. So, what can someone do? Are there things that we should look out for or recognize? How could someone best recognize that, hey, this is where you’re at, you’re in the cocoon right now and you need to pay attention to X, Y, and Z?

Chip Conley: So, the scholarship on this is really interesting there. When you’re in a transition, there’s really three stages to a transition, similar to what we were talking about with the caterpillar, the butterfly. But this has been discovered 110 years ago when it comes to rites of passages in indigenous tribes, but also, just in normal life.

So, the first stage of any transition you’re going to go through– actually, let me use someone going into the military as an example. So, you’re a teenager or you’re in early adulthood and you decide you’re going to go into the boot camp. So, you have to end something. You end your relationship as someone living in Fort Wayne, Indiana, going to high school, maybe community college. And now, you’re going to leave that life and go to Fort– what’s the Fort in North Carolina? I can’t remember the name of it, but you’re going to go and be in the Army and you’re going to actually go to boot camp. So, you ended something.

And we sort of as humans need to ritualize the end of something. We sort of do that for high school, we have graduation and a commencement, commencing adulthood. So, you go off to the Fort and you’re in boot camp and you get your hair shaved. You have this uniform you have to wear. You have a whole set of new rules. And you were in that chrysalis, you’re in that messy middle. You’re in that stage of life in which you have to live by and go through this opportunity to liquefy as a human in some ways, your normal habits.

And then on the other side of that, the third stage is the beginning of something new. And when you go back to Fort Wayne, Indiana, now you have a crew cut, you have a uniform, you have sort of a different stature and maybe a different confidence and maybe even a different way of communicating to people. That is what can happen.

Now, I just described it from the military perspective, but that’s what happens when you get divorced, the ending of something, the messy middle of like, oh, my God, I’m single. What does that feel like? And then the beginning of something new. So, being able to understand, there’s a famous book by a guy named William Bridges called Transitions. And then also one of our guest faculty members at MEA is a guy named Bruce Feiler, and his book Life Is in the Transitions came out two years ago, New York Times bestseller. I would recommend that book.

And MEA has an online course called Navigating Midlife Transitions. So, if you can understand that any transition you’re going through, especially in midlife, has those three stages, you can more ably go through the transition. What Bruce was able to show in his research in his book, Life Is in the Transitions, is that generally speaking, often it takes four to five years for a person to go through a transition, partly because they don’t know how to go through that transition more adeptly. Nobody has been given a master’s in transitions or they haven’t learned TQ, Transitional Intelligence.

Casey Weade: Well, I could stay on this topic for a long time, but I would be remiss if I didn’t head on emotional equations for a minute before we wrap. Back in 2012, you wrote the book Emotional Equations, or actually launched the book Emotional Equations: Simple Steps for Creating Happiness and Success. Can you just explain what are emotional equations and how they help us identify and learn from our emotions?

Chip Conley: Yeah, I was going through a really hard time. I had a flatline experience. I died, and then what’s called NDE, near-death experience. And from that, I had Viktor Frankl’s book Man’s Search for Meaning in my briefcase in the hospital when they were doing all this research, all this work on me to say, like, what’s going on with this guy? Turns out I had an allergic reaction to an antibiotic. So, while I was there in the hospital, I wrote an equation based upon what I read in Frankl’s book.

So, Viktor Frankl was a Jewish psychologist who ended up in a concentration camp in World War II, and he was able to see a psychologist who died and who didn’t. And that’s why his book is called Man’s Search for Meaning. And so, I wrote an equation, despair equals suffering minus meaning, with the premise being suffering is sort of ever-present, especially when you’re going through a difficult time, sort of a constant.

But despair and meaning are inversely proportional. The more meaning you have in your life, the less despair you have, even in difficult times. And that equation really helped me over the next two or three years when after I got out of the hospital and I went through a difficult time ultimately selling my company. And from there, I was like, okay, well, this is interesting. That equation around emotions helped me to understand them.

So, I started creating more of them, disappointment equals expectations minus reality. So, if you want to reduce your disappointment, you either increase the reality, like make it better, or decrease your expectations because expectations are often the doormat or the welcome mat for disappointment. Anxiety equals uncertainty times powerlessness. So, anxiety often has two ingredients. One is uncertainty, what you don’t know. And the other is powerlessness, what you can’t influence.

When you’re going through an anxious time, this is particularly true for leaders, if your company is going through an anxious time, the most important thing you can do as a leader is be transparent, offer as much communication as possible so people don’t feel like there’s an uncertainty of what is true and what’s happening. The more people get spun up when there’s not clarity, so it’s really important to be clear, and then help people to see in their own work how they can have some influence, what do they have some power over. And they’re not all bad. And so, those are all three – the anxiety and despair and disappointment are three of the equations, but there are 18 equations in the book. There are some real positive ones, too. There’s one on joy, there’s one on happiness.

Casey Weade: And I love all the equations. They’re fantastic and so meaningful, the life and these things that it’s like I just want them written everywhere so that I can just constantly go back and revisit these things. I’ve put a lot of things on my mirror. I think this is going to be one of those things that just ends up on my mirror every morning. I go, I’m anxious, all right. Oh, this is all I have to do. It’s just such a simple way of approaching life. And I love that about it.

But I want to get there with you because I go, ah, it’s been a decade. Maybe there are some new ones. So, what are you currently working on from an equation perspective? Are there things that are on your mind right now or new equations you’ve been thinking about or developed over the last 10 years?

Chip Conley: Yeah, it’s interesting. Casey, I can’t say that I have any new ones that I want to sort of display or talk about because there’s sort of information still. But I would say, let me talk about the happiness one because I want to study happiness in Bhutan. So, I went to Bhutan. Bhutan is the country in the world that actually first created the Gross National Happiness Index. So, what is this? Like, okay, how do you measure something like happiness that’s sort of an intangible?

Casey Weade: Exactly.

Chip Conley: Long story short, I came back from that experience and I was fascinated by the fact that happiness is not wanting what you have. And happiness is one thing what you have. One thing what you have means to have gratitude, to really appreciate the thing that you have. Happiness is wanting what you have, not having what you want. Having what you want is the idea of striving for something.

Now, you can feel successful when you strive for something and you got it. And that’s great. But often, there’s something called the hedonic treadmill, and once you’ve gotten what you were looking for, actually, you discount the value of it a little bit. We do this in dating, we do this in making money and our goals and things like that. And what ends up happening is we’re just constantly on this treadmill striving for the next thing.

And so, success can come from that, but happiness, on the other hand, tends to come from– the shorthand version of this is happiness equals gratitude divided by gratification. So, the fastest path to being happy in life is to appreciate or have gratitude for what you have. Gratification, on the other hand, the act of going out and trying to gratify yourself is a never-ending pursuit. So, the pursuit of happiness in the US sometimes can be a pursuit of gratification.

But pursuit of gratification doesn’t necessarily make you happy, it may make you successful. It may mean you have a lot of toys. It may mean a variety of things. But does it make you happy? Generally speaking, the data on this is pretty conclusive. Not necessarily, it doesn’t, so learning how to be full of gratitude.

Personally, my point of view on this one is I want the combination of both. I want to be full of gratitude and that I also am a striver by nature. So, I like being on that treadmill of it, but I need to be very cautious about am I pursuing things? Why am I pursuing these things? Am I doing it to impress my neighbors? Am I doing it because it’s the success script I was handed by my parents when I grew up? And it may not be the thing that’s most important to me. Am I doing it because I think I’ll be happier when I add an extra $50,000 to my salary annually?

I mean, the truth is that once people get to a certain level of income annually, happiness is not correlated with income. And it depends on where you live. In the US, it used to be $75,000. I think it’s higher than that today and I think it very much depends on where you live. If you live in Manhattan, it might be $200,000. But we tend to think that earning more and more and more and more will make us happier and happier and happier and happier. And the answer to that is it doesn’t. But if you’re only making $10,000 a year, you will get happier making 20 or 40 or 60 for sure.

Casey Weade: I’d love to dive in deeper to that. That can take us in a million other directions. But there’s a couple of pieces of wisdom I want to make sure I continue to pull out of you here. And that is one, you’ve had a lot of entrepreneurial ventures over the years. You referred to a lot of the failures you had there as noble experiments, which I think that would be great if we could see it that way. What a neat perspective. But what would you say to someone that is 50 plus, maybe 60 plus, and they want to take a leap. They want to start a new business, but they are afraid of failure. What would you say to them?

Chip Conley: Well, what I would say, the first thought is, number one is be careful. Like starting this business, if it doesn’t succeed, will the boat sink? So, I like to think of like, is it above or below the waterline? You’re like, think of yourself in a boat, and if you get hit by a torpedo below the waterline, the boat sinks. If the torpedo hits above the waterline, the boat doesn’t sink, it just doesn’t look quite as good because there’s some damage to it.

Starting a business is a function, and the fear you may have around it, there are three or four relevant fears. Number one is, if you actually fail, do you take your family down in some meaningful, difficult financial way? That’s an important question to ask. Do you have enough money saved? And is it really expensive to start this business?

Secondly, do you have the skill set? And if you don’t, how could you surround yourself with people who have skills that you don’t have? Thirdly, how could you actually do a little small bet by trying this business that you want to do in a small way to start with? Create a little consulting firm around it or moonlight and have this be your side gig and try to see, is there some business there?

So, I think, if you can do those three things, you can sort of give yourself the safety financially such that if the business doesn’t make it, you have it sunk the boat, make those small bets, as I said, and then surround yourself, have people in your team that actually have skills that you don’t have. Often, when we’re starting businesses, we want to start businesses with friends or a spouse or something like that, great, it’s okay to do that, only if they bring something to the table that you don’t have. But if your spouse or your friend is just like a replication of what you have, be careful because you haven’t really built a team that balances each other.

Casey Weade: Well, that reminds me of Dean Niewolny of the Halftime Institute, his low-cost probes talk. And I think that’s the beauty of being job optional. You can do such bigger things in the world once you know that, well, I have something to fall back on. Well, you can take some of these risks and you can have some fun doing it. Let’s wrap with this last question. What does retire with purpose mean to you, Chip?

Chip Conley: Retire with purpose means that you have more freedom, you have some time affluence in your life. Time poverty is often what we feel in our 40s, sometimes our 30s. And time affluence gives you some freedom, but it’s freedom with a sense of engagement in life. So, we’re not just eating bon bons and watching soap operas on TV or purely playing golf every day. There’s nothing wrong with playing golf, but doing it as the same thing you do every day, unless it has a greater purpose to it, you may get bored. So, it is having that freedom, that time and space, while also pursuing things that you may have wanted to do earlier in life but didn’t, and just like that pastry chef who used to be an attorney.

Casey Weade: I love that. Time affluence. Well, thanks so much, Chip, for joining us. Before you leave, I want to make sure we offer all of our listeners something special. We partnered up to offer your book, Wisdom at Work: The Making of Modern Elder. And we’re just going to give that away for free.

And if you’d like to get your free copy of Wisdom at Work, all you have to do is this, all you have to do is subscribe to the podcast, write an honest rating and review over on iTunes, and then shoot us an email at [email protected] with your iTunes username. We’ll verify that and we will send you the book absolutely free. It’s really that easy. Chip, thank you so much for joining us. I look forward to doing it again.

Chip Conley: Thank you, Casey.