Chip Conley – Airbnb, Modern Elders, Navigating the Midlife Crisis

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So Chip, great to have you on the program. I think I first heard you talk at The Long Now Foundation, I think this group was set up by a previous guest Kevin Kelly. How do you answer the dinner party question “what do you do?” 

I pose it back and say “what do I want to be?” So it’s not about being a human doing but being a human being. When I would answer that, I would say I help make aging aspirational, which is a heavy lift. Most people don’t think of aging as being aspirational. But that’s really what I do today based upon my recent launch of The Modern Elder Academy. 

And the backstory is you’re a very successful hotelier, you sold out in the depths of the recession, then you took a role at Airbnb, which began this journey towards making aging aspirational. Is that a fair summary? 

That is a very fair summary. I was a boutique hotelier for 24 years, started a company called Joie de Vivre based in San Francisco, became the second largest boutique hotel here in the US, but after going through two once-in-a-lifetime downturns in the same decade, I was ready to get out of that business. When I left that, the Airbnb founders approached me and I thought that sounded like an interesting way to democratize hospitality, as of course you, being in Europe, understand the idea of home sharing was in the process of growing. I joined them six and a half years ago. But the thing that was most noticeable to me after I joined them was like “oh my god, I’m twice the age of the average person here.” Over the course of the next few years, in a loving way, I was started to be called The Modern Elder at Airbnb, who was as curious as they were wise, and yes, that led me to writing a book called “Wisdom at Work: The Making of a Modern Elder,” which led me to creating the Modern Elder Academy. 

Maybe we just go back to the describing that phase in your book. You refer to yourself as the male Margaret Mead amongst millennials. Your books are peppered with references to anthropology, which, as we discussed earlier, is my background. What did it feel like being a male Margaret Mead among the millennials? What happened? 

I hadn’t thought about this. What was interesting in the way that the three young founders had approached me, was that I was this person with wisdom, or actually with knowledge. We didn’t talk about the word wisdom. It was more about knowledge about hospitality and leadership, and how to create a company and grow it. So that was what I was supposed to come to help them with. What I didn’t realize was I’d never worked in a tech company, and I didn’t really understand the lingo. Yes, I was in fact exactly twice the age of the average employee in the company. So I guess they came to realize pretty quickly that I was not there just to be purely the mentor, but I was also the intern as well. In order to be Margaret Mead, it forced me to, instead of being judgmental, because a lot of times when you’re in a place where you feel awkward or not completely comfortable, you may use judgment as a way to get yourself out of that place – well, I decided to use curiosity instead. Instead of looking at these millennials and calling them names, I looked at them and said “I want to learn from them.” So that’s why I would consider myself the Margaret Mead, in the sense that I think a cultural anthropologist is a very curious person, because they come from the perspective that they are in someone else’s habitat, in the process of studying that person. So rather than take their own personal habitat and impose it on someone else, I was there to learn from that habitat, and there was no doubt that being in a young tech company in Silicon Valley at this time of my life meant that I was in their habitat, not mine. 

And I’m curious, maybe there’s a bit of post-event rationalization in that, but at the moment you discovered that this was deeply uncomfortable, was there a point where you decided not to judge, but to be curious? It sounds like a lovely narrative, but what did it feel like? And how did you decide to go that route versus saying “to hell with this, I’m going to bail out because it feels like too much hassle at this stage in my career?” 

It felt bloody awful. I was going on a hike with my father about a month or so after I joined, and I was in the process of thinking about quitting, because I was fearful of the idea that a man at 52 years old, having had a pretty good history and success story, I might fail at this. I felt like I was carrying a heavy weight, and frankly, it was the weight of all of my past successes and my sense of identity in the world, that I am a successful business person. And I was worried that this new thing I was doing would make me look like an idiot, because I wasn’t sure if the company would succeed first of all, and secondly, I just thought I wasn’t necessarily well packaged to be able to work in a tech company in my 50s. What I had to do was go through a right-sizing of my ego, which meant I was not going to be the person on stage, I was going to support these founders, and they’re getting the headlines. And for someone who’d run my own company for 24 years that was a little hard, but it was good. It was very good and it was what I needed. I also had to get comfortable with the idea of being the dumbest person in the room, and sometimes the wisest. I had to get comfortable asking sometimes really naive questions. It was a naive question about a word I didn’t understand. I wouldn’t bring it up in front of everybody, I’d make a list and then I had some young people who worked for me and I would go to them and say “what does it mean to ship a product or ship a feature?” I had no idea. So in the software lingo of Silicon Valley I learned a lot. But I also sometimes asked questions that were sort of naive, but they’re really wise in terms of identifying a blind spot that the company had. I eased up on myself, instead of trying to think I had to be the wise mentor, I realized I could be the curious or naive intern as well. And once I got comfortable with the idea that people were okay with that, it became more of a fascinating journey in having a beginner’s mind. 

Did that require some renegotiation in terms of what your scope and your remit was, or did it evolve in a collaborative way? I think Brian was the guy you worked closely with, right? 

Yeah, they cut my salary in half, haha. They said “you are a student, you’re not a teacher.” 

Nor a mentor, you pay to work here. 

Do you know what was actually interesting? A few months into it, Brian pulled me aside and said “I don’t want to do a formal review for you yet.” And I was like “oh, thank God, you’re 21 years younger than me, I need a week or two to prepare for that one.” But he said “but I want to give you some advice. You’re doing a great job, everybody’s loving you, but you feel a little bit reluctant.” It was interesting, I realized that there was a part of me that felt reluctant because first of all, I planned to just be there 15 hours a week and it turned out to be 15 hours a day, so it was a much bigger endeavor than I had planned. But I think there was also a sense of being fearful that I wasn’t what I thought I was supposed to be, meaning the person who’s just dispensing wisdom. And I said to Brian “I just feel a little awkward because I do feel like I’m learning as much as I’m teaching.” And he said “OK, you know what, that’s actually why people love you, because of the fact that you’re not just a parent or a preacher at the pulpit, spouting wisdom, you’re actually in the trenches with people learning as much as they are.” And you may be learning digital intelligence from them, and they’re learning some emotional intelligence from you. And once I realized that Brian, as the CEO of the company and my boss, but also the person I was supposed to mentor, was seeing that this idea of being a modern elder was a good thing for the company, that made me feel like “wow, maybe I can have a role here that actually will be valuable” and as it turned out, it was very valuable. 

It’s fascinating because it’s a unique story, but part of the backstory here is that more and more people are finding themselves working for people who are younger than them. I’m sitting here in Basel, there’s a 43-year-old CEO of a top five pharma company, which is different from a twenty something CEOs of their own startup. This is a mature business worth a quarter of a trillion dollars and the CEO is 43. What’s going on in the workplace that encouraged you to write this book? Clearly you feel this is a relevant message or story for lots of people in the workplace.

I think what’s fascinating and what has never happened before in society is that we’re all going to live a lot longer. Now that’s been happening for the last hundred years. On average, we’re going to live 10 years longer than our parents. What’s new is that power is moving 10 years younger. I talk about this in my book “Wisdom At Work,” because there’s data that shows this. Power is moving 10 years younger because of our increasing reliance on digital intelligence or DQ. So if we’re going to live 10 years longer, and power is moving 10 years younger, what we’ve created, without intending to, is a new 20 year irrelevancy gap for people in midlife. And yes, in fact 40% of us have a boss that’s younger than us, and by 2025, the majority of us will have a boss that’s younger than us. So we’re living in a world where it’s almost like if you’re midlife, and in some industries like tech or entertainment or advertising, people start feeling irrelevant in their mid 30s. So the risk here is that people are going to live a lot longer and feel irrelevant a lot earlier, and if that’s true, we have the potential for a catastrophe for a life stage that already wasn’t well regarded which is midlife. My premise is how do we help people in their life repurpose themselves as a modern elders, so they’re curious to constantly be learning what’s new, while also minding their mastery and having wisdom as well? And then how do we help companies realize that these young digital leaders, who are doing startups or they’re running pharma companies that are worth as much as you’re talking about, they could use some wisdom as well. They’re often exceptionally smart at a particular narrow area and technology like digital, but they don’t often have as much life experience and wisdom around humans and emotional intelligence, and leadership. That is something that you actually gain over the course of your lifetime. So I think that part of my role in writing these books and creating the Academy, is to help society and companies realize mixing a modern elder with the Young Turk is not a bad idea.

Yeah, you make the point that this is a diversity play, and I don’t mean that in a simplistic way. Everyone talks about diversity around gender, but this is around age diversity, which brings out very different things in terms of teamwork and team effectiveness, right?

Correct. There’s so much evidence at this point that diversity is a very valuable element in teams and companies, partly because it helps people get out of groupthink. And the idea of groupthink actually means people think quite narrowly and not think about all the options that are available. Our focus on diversity has predominantly been focused on gender, race, and sexual orientation. And I’ve proposed that age should be just as important of a demographic in thinking about this, and there’s some actual evidence for this. Young people are exceptionally focused, they do things fast and focused. Older people, when it comes to solving problems tend to take longer, but they make fewer mistakes, they’re also less willing to take risks. So you take someone who’s older, who can connect the dots, think holistically with someone who’s exceptionally focused and younger, and you actually build in more wisdom, a wider aperture of wisdom.

So some of the skills that an elder brings, and we should also define this, an elder isn’t someone necessarily with gray hair. I think you’ve got quite a broad definition of an elder, right?

Let me define it. So elders are not elderly, elderly is maybe the last 5 or 10 years of your life. Elder is a relative term, elder is a function of who you’re surrounded by. So if I was 52, surrounded by 26 year olds, as was the case at Airbnb, I was the modern elder at Airbnb. And I believe a modern elder is different than a traditional elder in the sense that they are as curious as they are wise. It’s not just about the wisdom. 

What were the skills that you had to unlearn and the skills that you had to learn once you had this moment of insight around having to shift your identity? What were some of the skills you had to stop exhibiting and some of the ones you had to learn?

I think there are four key lessons that help evolve someone into a modern elder. The first lesson and I write about this in my book, the first lesson is Evolve. And evolve basically means you need to strategically edit what is working and what’s not in your life. For me what that meant there’s some of my knowledge historically, which wasn’t all that valuable in the world of home sharing. It doesn’t really matter how many rooms are made clean in eight hour shift in the world of Airbnb hosts or Airbnb as a company. Some of my knowledge I had to just let go of. So my identity like being the CEO of my own company, I had to let go of. To evolve, the first lesson is saying “be open to having an identity and knowledge that is constantly being renewed.” The second lesson is about learning. Instead of actually going into the workplace focusing on how do I give all my knowledge or wisdom away, instead, focus on what it is you don’t know yet. If you are someone who has lost your sense of curiosity or willingness to learn, you are definitely in the process of dying. And yet, we see some of the people who are most alive in their 90s, are people who are generally curious. So the second lesson about learning, for me that meant having to be open to being a someone in an industry, a technology that I had no knowledge of. 

And you quote Drucker in your book as being a great example of that, right?

Peter Drucker lived to his mid 90s ,and every two years he would study a new subject that had nothing to do with being a management theorist. He wrote two thirds of his 40 books after the age of 65, and he was basically somebody who just saw curiosity as an elixir for life. So that’s the second one. The third lesson is Collaborate. This is where we start getting into more of our comfort zone. As we get older, our emotional intelligence tends to grow, which means that we actually have pattern recognition at understanding ourselves and others. And that pattern recognition means that we understand how humans work. In the context of teams that can be very valuable, because one of the things that I learned at Airbnb was like “oh, my god, there’s a lot of smart people in the room,” maybe too many smart people in the room, maybe too many smart people in the room trying to be smart in front of each other, and competing with each other. Ah, I have a role here. I’m the collaborator, I’m the one who brings these people together. That helped me to actually be very valuable, because even in a tech company which is focusing on something that doesn’t sound like a very human-centric technology, it’s filled with humans and being the one who knows how to collaborate helps. And that finally brings you to the fourth lesson, which is to counsel. [19:49] [keywords: wisdom, learning, credibility]There’s no doubt as you get older, and hopefully wiser, more people will be drawn to you because they see you as someone who can offer them some wisdom. And yet I see that as the fourth lesson, because I think if you go straight to that as an older person, you haven’t necessarily earned the credibility of the people who you’re going to be lecturing. I think lecturing people is not what you want to do as you get older. I think what people want is asking great questions, and welcoming people to learn from you is great, but it’s not something you impose on someone. 

And I think you use the distinction being a sage from the stage or a guide from the side. That’s the language you use, which characterizes that.

Yeah, being able to be arm in arm with someone that you’re going to help teach. But I think more than anything it’s about mutual mentorship. The way we got wisdom in the past is, there was an older person and a younger person, younger person was the apprentice. Today, or 10, 20 years ago, Jack Welsh, who was the CEO of General Electric, created something called reverse mentorship, because he knew his senior executives at GE needed to learn from young people, and it was specifically about the internet and computers. But today I think it’s mutual mentorship, which means that you could have someone you’re mentoring, but they’re going to actually mentor you as well, there are things that they can teach you. And this idea is really new, because of how much value we give to digital intelligence. And generally speaking, younger people have more digital intelligence than older. 

So I’m curious, in a lot of my world, and my background has been in large organizations, often the need to do this is forced upon one, either because of restructuring or cutbacks, or from your point of view, even though you’re an entrepreneur, you had a life altering, flatlining experience. How can people get in front of this, rather than having a really challenging wake up call? What other things can people do to get in front of this, and avoid the pain associated with those kind of wake up calls?

First of all, I think if you are naturally curious in your life, and you try to almost think of that as a skill that you’re going to build as you get older, I think that’s a really good starting point. 

But in the absence of that, because lots of people say that, but in practical terms you get into your ruts, your routines, and curiosity isn’t always valued in process driven organizations. 

It doesn’t mean you can’t be curious. In a process driven organization, efficiency rules, the gods of efficiency do not like curiosity, curiosity is not an efficient way of thinking because curiosity opens up possibilities. That doesn’t mean you can’t, on your own, even if it’s in private, focus on your own curiosity. Like I said with Drucker, he was focusing on a new subject every two years, and nothing to do with being a management theorist. So he could have been in a very process oriented organization. But that’s his way of exercising his mind. I’m not saying you have to do this in your day to day work environment, especially if it’s not prized. But the truth is you do need to get better as you get older at being able to develop environmental mastery, which basically means you understand what habitats you will flourish in. And if you’re in an environment where you want to be curious, and the environment is not naturally curious, then you may find that there’s a better environment out there for you elsewhere. I would say that’s one thing to do. Another thing to do, a little more practically speaking, in the workplace, especially in a very processed driven place – how could you find someone younger than you, assuming we’re talking right now to people in midlife, let’s say people in their 40s, or 50s, is there somebody who’s a generation, or even two, younger than you, that you could create a mutual mentorship relationship with? I’m not suggesting you go up to somebody who you’ve met in one meeting, and you’ve heard them talk and it sounds smart, and you just say “can you be my mutual mentor?” That’s like popping the M question for marriage a little too early. Instead, go spend half an hour with them having tea or coffee, without any expectation of that growing into some kind of mutual mentorship. And the truth is, with all of the mentors that I had at Airbnb, I would say 80% of the time we never use the M word. It was just I learned from them, they learned from me, and we had an ongoing cadence of having a few minutes with each other every once in a while. I think doing that and creating that kind of mutual mentorship relationship in your life will serve you well in terms of not only building relationships with a bunch of younger people in the company, but also teach you a few things. 

Then, going from Airbnb, you founded the Academy to essentially teach people some of these skills, and help them, I won’t say reinvent themselves, but I’ll use your language, in a midlife pitstop versus the old model which is fueling up through university for a one tank journey.  

Yes. We talked about lifelong learning, and we have precious few places where people can get that. Online there are more and more places to do it, but you can feel pretty lonely online as someone who tries to learn something new. The social crucible of a place where you can actually feel curious and dumb at the same time as feeling appreciated doesn’t exist. What was curious to me was, we have a growing need, I believe, in the workplace for modern elders, but we have no place where we mint them like we mint coins. I wanted to create the world’s first midlife wisdom school to try to do that. We started with a beta program for the first half of 2018, got a lot of lessons from that, and then we opened to the public in November 2018, and we’re just finishing our academic calendar year now. We’ve had 500 people go through the program at this point from 17 countries, a number of people from Europe. And it’s been phenomenal in terms of the overall satisfaction levels, way above what I thought it would be. What’s most interesting to me is the sense of connection people feel at a point in life where frankly, people are pretty silent about all the things that they’re going through in midlife, and this is a place where they come together with a group of 16 to 18 people for a one week program on a beach front in Mexico. They get vulnerable and they learn from each other.

Wonderful. And the whole learning thing, I’m really interested, your profile is you’re an entrepreneur. Do you see people from a more structured corporate environment finding this journey easier or harder than perhaps an entrepreneur? Any trends there? I’m kind of projecting my journey a little bit onto this, which maybe is the wrong thing to do.

No, that’s okay. I think it’s hard. The more you’ve been in a structured environment, where the hierarchy has historically been old to young, meaning the power rests with the older people, to be in a world today where power is moving to young people quickly feels like “wait a minute, I was paying my dues, and now I’m getting to the age where I’m supposed to be the one in charge, and I now have a boss that’s 10 years younger than me, what happened here?” I think part of the reason why the millennial generation gets a bum rap from society is because we envy them, because they grew up with the dominant technology in their young years, as something that they could use that’s valuable for them now, because they learned the internet, they learned computers at very young age, whereas, I don’t know about you Mark, but my dominant technology I grew up with was TV and it didn’t do much for my career. So I think the more structured of an environment we’re in, the more of the free floating world we are moving into, where everybody’s an entrepreneur and all companies are trying to be tech companies, is confusing and confounding, and it requires a bigger leap to move to a place where you’re able to be relevant in this new world. 

Yep, got it. Well, let’s make a quick leap now to festivals, and this is getting into the anthropology piece. I’m really interested in where does your passion for festivals come from, and what attracts you to them? Because I think you founded a business around festivals, didn’t you, or a website at least?

Yeah. First of all, I’ve been going to festivals of all kinds for a long time. When I sold my company Joie de Vivre and had some time off before I joined Airbnb, I got curious about the fact that I was on the board of an organization called Burning Man, which is a festival just outside of California in Nevada, sort of arts festival in the desert that’s famous. And I was like “why is it that there’s a growing interest in festivals in the world, which are basically an in-real-life experience, at the same time that we’re getting more digital?” Like, the more digital we get, the more ritual in person we seem to need. So I decided to go around the world to study festivals of all kinds, and I went to 36 festivals in 20 countries, religious pilgrimages to music festivals, to arts and cultural festivals, to food festivals, film festivals as well, and then created this website Fest300 with a co-founder, and ultimately merged it with a company called Everfest, but I had to step away from it as as soon as the Airbnb founders came along, because that required all my time. Émile Durkheim, a sociologist, defined this 110 years ago as collective effervescence. The idea that when you’re in a place where people have a common mission or common purpose, your ego starts to evaporate in a sense of calm and joy, and collective effervescence grows. And I think that’s a really interesting metaphor for many things that work in life, when you are in a place, even in the company, or at the Modern Elder Academy, where your sense of separation seems to start to evaporate, and you feel this sense of common purpose and calm and joy. That’s why people go to festivals. That’s why people love being in a company where it’s working well. That seems to be why The Modern Elder Academy has become so popular.

Yeah, and as for the anthropological piece around Durkheim, the sociologist, as you talked about, there’s a ritual associated with transitioning out of an organization to reinvent oneself, to reappear in a different state. That’s one interpretation of your journey I guess, isn’t it?

Yeah, I think that we don’t really have rituals in midlife. So society has created, over the course of thousands of years, rituals during periods of people’s lives when they’re going through transition, whether it’s puberty, or moving into adulthood, or getting married, having babies, or dying, we have actual rituals, we have celebrations that help people through those times. We don’t have that in midlife, because midlife is a relatively new phenomenon in the history of humankind. I believe that creating some ritual, creating some, in our case, The Modern Elder Academy, a place where people can have a ritual around midlife, is a very valuable thing for society, as well, of course, the individuals in society. Because without ritual, without that sense of community support, going through a transition can be really difficult. 

Absolutely. I suppose the Academy is providing, to some extent, some rituals associated with that transition.

That’s right. I can’t go into the details of each of these rituals, but the rituals are meant for people to understand what it is that they’re leaving behind, and what they are moving toward. Rites of passage as a premise, and you know this because of your anthropology background, Arnold van Gennep popularized the idea of it, having studied indigenous societies. There are three phases to it, there’s severance from the past, there’s the liminal period of transition, and then there’s going back into society. That kind of three-step thing is part of what our rituals are meant to do, part of what the Academy is doing, part of what, frankly, in the US, we call going to military boot campus. If you’re going into the military you leave your family and society, you go and you get your hair shaved, and you go to this boot camp environment, which is this liminal period. And then, on the other side of it, when you’re finished with your military work, you’ve got a new discipline or a new whatever that you have from that experience. That kind of Hero’s Journey, as Joseph Campbell called it, speaks to many things in life, but we don’t think of midlife that way. And I’m trying to help people see that that’s a good way to look at midlife.

Yeah, although there is sort of a cliche of the midlife crisis, of the sports car and the young partner and then getting over it and reappearing. I guess that’s an example of it, even though it’s not actually ritualized per se or not embraced per se by mainstream society.

I would say, because I don’t think that that’s a ritual that society sanctioned or supported, I don’t think it’s a ritual. I think it’s a way of operating in the absence of rituals. You could go out and drink yourself, silly, as another approach, but that isn’t necessarily a ritual. I don’t know, maybe a UK soccer match, that’s good. 

Are there any companies that are embracing this, that are putting in place these rituals? I think you mentioned Procter & Gamble are recognizing this new reality of demographics, and purpose and learning. Are there any companies that are doing this really well in your experience?

Well, Airbnb is doing it now, just because they stumbled upon it. I think there are two sides of it. There are older companies like Procter & Gamble, that have created a mastery society for their older workers to actually help figure out how someone’s developed mastery, and that they have a share. So that’s an older company figuring out how to offer that to younger people. And then there’s the Airbnb and some tech companies, a company called Atlassian, an Australian large software company that’s doing this as well, where they’re figuring out how to share this older wisdom, because these tech companies don’t have a lot of older people. How do you take that wisdom and apply it to younger people, and then have it go in both directions? But it’s a relatively new phenomenon, so I can’t say there are a lot of companies that are the role models yet.

I think I remember you saying in the Q&A that you’d had the interest from corporates to run the Academy like programs in house, but it’s in early days?

That’s right, we’ve had a lot of interest from companies that would like to come to the Academy and bring their teams. We’ve had already companies that have done that. And we now have companies that are actually sending people in midlife to go to the Academy as a way of renewing themselves.

Interesting.  When I came across your work, it just resonated on a number of levels with me and with the kinds of people and organizations I work with, because there is clearly a need for this, and there seems to be very little available to help people on this journey.

Yeah, that’s what’s phenomenal. And I think that 40 years ago, we’ve had spas and health retreats probably for a long time, but it’s been 40 years since something called Canyon Ranch was created as a destination spa resort, to help people, often in midlife, figure out how to get back into their bodies. Similarly, I think it’s time for us to help people in midlife to get back into our hearts and souls about what it is that we’re here on Earth to do. Until The Modern Elder Academy came along, there really wasn’t a place that was dedicated with a curriculum specifically for people in midlife.

Lovely. Well, I’m mindful of time, Chip. A couple of questions I sent through to you recently, apologies for not getting them out to you earlier. First question, what have you changed your mind about recently?  

I think I’ve changed my mind about the idea that aging can be aspirational. I don’t think aging was aspirational in my perspective in the past, and I’m actually starting to imagine maybe it is. The new curve of happiness, which shows that people get happier as they as they get older.

Unless you’re Russian. 

Unless you’re Russian, exactly, haha. 

I love this concept. Maybe you can just describe it a little bit?

Sure. So social scientists, pretty much across the world, except for in Russia, have found that as people age, they get happier. It’s a surprise because the societal narrative is quite the opposite. As you go to midlife, you have the midlife crisis, and then you have disease and go to decrepitude after that. But in fact, people do get happier, and it’s for a variety of reasons, generally around the idea of moving from the accumulations part of their life to the editing part of their life. When you move into an editing mode, you start focusing on that which is important to you. It also means that there’s a lot of responsibilities that tend to happen up to about age 45 to 50, that you start to evolve out of, which means you have a little bit more freedom. You’re less worried about what people think of you, and what society expects of you. You’ve sort of gotten over the disappointment about the things that didn’t happen the way you wanted them to. And very much you start focusing more on the moment. People, as they get closer to their death, which if you’re 50 years old is maybe a long time from now, but as you get older and closer to death, you actually are less focused on the future, you’re more focused on the present. When people move into that place of the presence, they tend to get into a more content or happier place. So those are all the reasons. I think my key lesson is aging can be aspirational. Although, if you’re playing on the playing field of youth, which is your body, you will constantly be having an uphill climb, because it’s harder to keep that body in shape, and your face looking like it did when it was 20 years old.

Okay, and then second question. Where do you go to get fresh perspectives, especially when you’re facing tough challenges?

We all have to know, where do we get renewed, what are the places that just feel fresh to us. For me it’s running on a beach. When I’m running on a beach, I don’t care what’s happening to me, during that 30 minutes that I go for that run on the beach, it feels like I’m renewed. So, often when I am most in need of some rejuvenation, or a shift in how I’m looking at things, I’ll go for a run on the beach, and then I feel like I get a download from the heavens, of different ways of looking at things. 

Lovely. I read that you’re a great fan, as I am, of Viktor Frankl’s work and that struck me as being a wellspring that many people go back to when they’re facing challenges. But you, like me, reach for the physical exercising route as well.

There’s no doubt there’s a lot of great books out there that do it for me as well. That Frankl’s book “Man’s Search for Meaning” has always been an inspiration. If nothing else, for those who don’t know the book, it’s about a psychologist in a concentration camp in World War Two, and if you think you’re having a bad day, week or year, read that damn book. You’ll realize your problems are petty compared to what Viktor Frankl and people in concentration camps had to deal with.

Yeah. Quick aside, I mentioned to a friend of mine today that I was interviewing you, and she was terribly excited. And I said “What do you want me to ask Chip?” and she said “what are you reading at the moment?” So let me ask you that question, Chip. 

There’s a book I love from the UK called “The 100-Year Life,” which I just read. 

Lynda Gratton.

Yeah, exactly. In fact they were on your show, I think. I read that book a year ago, and then I read it again a month ago. And in re-reading it a month ago, there were things I didn’t see the first time. I love that book, because it really says if it is true that about half of the people in Europe or the UK who are being born today are going to live to a hundred, we need to really rethink how we structure our lives and society. Another book that I’m just starting to read right now is called “Elderhood” by a woman named Louise Aronson. So it’s very interesting, that the word “elder” is starting to proliferate out there. This is a now a New York Times bestselling book, so the idea of elders is catching on. What else am I reading? I just read a book by a guy named Mel Zuckerman who created Canyon Ranch, and it’s called The Restless Visionary. So it’s a personal tale of him. I have so many books, I love reading. 

Lovely. Well, that’s one of the joys of doing this podcast, I get lots of stuff sent across to me, so I’m never wondering for a good read. But thanks for those, she’ll be thrilled that I managed to get the question in. So my final question, what’s your most significant failure or low, and what did you learn from it, and how have you applied that learning?

I think I’ve had many, haha. Which one should I choose? One of my lessons was when we created a boutique campground, seven years before the word glamping was created, and this is basically a place where people could come, and without getting their hands dirty hang out in nature in a tent that has been created for them with down comforter and mattress, etc. It was very nice but it was way ahead of its time. In retrospect it failed, and we ended up having to sell it for a big discount of what we’d have invested into it. And yet, it absolutely taught me something about what people’s changing habits are around group and corporate travel. People would come and want to do yoga retreats, that was just 20 years ago, at a time when we never imagined corporate travelers or groups of corporate trip guests would want to do yoga retreats. Ultimately, it led me to creating something called the Hotel Vitale in San Francisco, which became the most successful upscale hotel in San Francisco. So a failure led to a success. And I guess that’s really the key message here. The lessons I’ve learned from my failures, and there’s a lot of them, have led to some of my biggest successes, and including, I can go back to what we started with, the first month at Airbnb I felt like a failure, because I didn’t understand this new world I was working in. And yet, being open to acknowledging my sense of failure and my sense of having to be in a new space, and having to renew myself in a new way, helped me to get to a place where I could become a modern elder. So out of what felt like a failure, I was able to create success.

Wonderful, wonderful. Well, I must say, having discovered your work, I will follow the Academy, and if it ever comes to Europe please let us know. Now where can people get in touch with you, Chip?

They can find me on social media, Twitter, LinkedIn, Facebook, etc. On LinkedIn I have a bunch of articles I’ve written, so you can find some of my articles there. And then there’s the website, and attached to that you will see website.

With some lovely pictures, it really does look hugely compelling, not just content wise, but also the surroundings look really beautiful. 

Thank you. 

Wonderful. Well, Chip, thank you very, very much for your time, I have been looking forward to this for some time. Really appreciate it, and look forward to meeting you in person one of these days.

Beautiful. I’d love that as well. Thank you, Mark. 

Have a good day. 

All right. Bye.

I find stories of leaders who have successfully reinvented themselves mid-career both compelling and informative. This is mainly because I have been on this journey for the past 4 years and am always on the look out for guides.

Chip Conley has successfully made this transition, and is now helping many others take the same journey. Rather than being a “sage from the stage”, Chip describes himself as a “guide from the side”. His story of going from founder and CEO of the leading chain of boutique hotels in the US, Joie de Vivre, to being essentially an intern at Airbnb and mentor to founder Brian Chesky, will be of interest to anyone feeling overwhelmed by changes in their industry, or worried about becoming irrelevant in the workplace as a result of technology or other disruptive forces shaping our world of work.

As a result of his experiences at Airbnb, and the success of his latest book “Wisdom at Work: The Making of a Modern Elder,” Chip has recently launched The Modern Elder Academy, with the tag line: Where midlife mastery is the launchpad to growing whole, not old. In our conversation he tells his story.

What was covered:

  • The emergence of a 20-year irrelevancy gap in the workplace for people in midlife
  • What is The Modern Elder and how companies can benefit from age diversity in the workplace
  • Four key lessons for bridging the irrelevancy gap and re-establishing value of this age category: Evolve, Learn, Collaborate, Counsel

Key Learnings and Takeaways:

  • How people in midlife can repurpose themselves as modern elders in order to integrate their mastery and wisdom with the digital intelligence and focus of younger generations
  • Mutual mentorship – a new form of relationship where both sides are simultaneously learning from and teaching each other
  • The need to regard midlife as a transition period and create modern rituals to support that transition

Links and Resources Mentioned in This Episode:

Mark Bidwell

Mark Bidwell

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