The Bregman Leadership Podcast
Episode 192

Chip Conley

Modern Elder Academy

What’s the difference between starting at 26 versus beginning again at 50? We have a system in place to support adolescence, but not so much so with middlescence, says Chip Conley. He founded the second-largest boutique hotel brand, Joie de Vivre Hospitality, when he was just 26. After selling the company over twenty years later, AirBnB invited him to their team as Global Head of Hospitality and Strategy—and he found he was just as much an intern as a mentor in the youth-oriented then-startup. Now, he’s the founder of Modern Life Academy, which offers a series of workshops on managing midlife. Discover what happens when you become shackled by your calling for two decades and how to know when it’s time to make a major shift.

About

Website: ChipConley.com
Bio: New York Times bestselling author Chip Conley is the hospitality maverick who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand. In Wisdom@Work: The Making of a Modern Elder he shares his unexpected journey at midlife — from CEO to intern — learning about technology as Airbnb’s Head of Global Hospitality and Strategy, while also mentoring CEO Brian Chesky. Chip is the founder of the Modern Elder Academy, where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico. He serves on the board of Encore.org and the advisory board for the Stanford Center for Longevity. Portrait credit: Lisa Keating.

Video

Transcript

This transcript is unedited.

Peter:

With us today is Chip Conley. He is an American hotelier. I don’t even know if I’m pronouncing that word correctly. But he started the joie de vivre hospitality, which is a brilliant hotel company that basically and chip will correct me if I’m wrong here, but I know from having stayed at a few that basically gives personality and character to each hotel so that rather than staying at, you know, a run of the mill cookie cutter hotel, you’ve, you’ve, you’re, you’re staying in a hotel with some, you know, very particular brand personality connection that makes it a lot more interesting. He started that at 26. He held the position of CEO for 24 years. He has done a bunch of other stuff in between, but I want to talk with him. We’ll, we’ll, we’ll talk with him about his journey, but he is now very focused on a movement is what I’m going to call it, but focused on being an and, and sharing about and helping people come along in this movement of modern elder. He’s done. He’s created something called the modern elder Academy. And actually rather than explain much about it to you, I’m going to let that unfold in our conversation. So, chip, welcome to the Bregman leadership podcast.

Chip:

Thank you, Peter. It’s an honor to be here. You know, last time I saw you was in big Sur California.

Peter:

Yeah, I was chip and I were reminiscing a little bit that the SLN, which is a place that we teach that I teach at chip is on the board of in big Sur. It’s the most beautiful place you will ever visit in your life. I think it’s one of the, it’s really the most beautiful place I, I spend time in. And it’s a great place to reach juvenate and connect and learn some interesting stuff. And they do have naked hot tubs which are really, you know, hot Springs native to, to the land. That’s really the hot Springs. And and so I was saying to chip last time I saw you, we were both naked in a hot tub and and so from, from there to here.

Chip:

Well, I’m glad to be here. It’s, I’m coming to you from Austin and I think you’re in New York and you know, it’s cold. It’s actually cold here too right now, this time of year.

Peter:

Yeah. And in fact, it hasn’t been cold enough here at this time of year. I think we’re in our forties, and I don’t know that we’ve ever, like, we may have had two or three days of winter, but I’m a big skier, so it’s a little frustrating to me that we haven’t had some really good snow making or snowing rather. So. So chip, let’s I want to get to modern elder Academy and I want to go to modern elder Academy. So we’re going to talk about that and I’m going to see if I can, I can, you know, get there because it’s so resonates with, with what I’m what I’m looking at right now in my life. But before we get there, I want to take a step back and, and walk through your history a little bit and how you’ve become the person that you are now, which obviously relates to being an elder. I’m curious, by the way, why at 26, you decided to start a hotel company, which is, you know, an ambitious move.

Chip:

Yeah, thank you. Well I was a couple of years out of Stanford business school and so I had a business focus but, and, and real estate focus, but I was, I wanted to do something that was a little more creative and I could see the boutique hotel movement was starting to take off. And I decided, I, and I, plus I had a lot of threatens who are visiting me in San Francisco, staying on my couch. This is before the term couch surfing existed. And so I, you know, with, with a focus group of about 10 or 12 people stay on my couch, I found out that if I could create an affordable hotel that had personality that had some nice design I might be able to make a business out of it. And my first hotel was called the Phoenix. It was a broken down pay by the air motel in the Tenderloin of San Francisco, not a nice neighborhood. And I’m 33 years later, it’s still the rock and roll hotel of San Francisco and I created 52 boutique hotels during that time. Running the company.

Peter:

Yeah. It seems like such a bold move. Right. Cause it’s also, you know, like now people often start businesses in the ether and it’s, it requires, you know, some investment and some commitment, but it’s, you know, that’s an old school business to like actually the business itself is, requires brick and mortar. Like it is, it’s not Airbnb. And we’ll talk about Airbnb in a sec, but I’m curious about like, whether that’s something you think is easy. This is a strange question, but is that something that’s like easier to do at 26 than it is at 56?

Chip:

It’s a really good question. Because it’s one of the questions we talked about at the Academy. Why is it that we have more of an openness to being what we call liminal being in transition, maybe being awkward in the beginner’s mind earlier in our life where as we get into midlife and we’re less inclined to the reasons it’s easier earlier are the following. You have less to lose you, so you, you’re often not in a position where you have kids or family that you’re helping to fund. I think also there’s an element of you don’t know what you don’t know. And so there’s an element of like, okay, I’m willing to do it because it, it’s worth the risk. I mean, I think as you get more experienced, and there’s actually some great data on this now from the Kaufman folks in Kansas city, Missouri where they’ve been able to study that genuinely, people in their 50s are more successful than people in their twenties or thirties that starting businesses now, this flies in the face of what we see in Silicon Valley. Right. And, and you know, the Mark Zuckerberg and, and the Brian Chesky from Airbnb’s, but the fact is as you have more experience under your belt, you actually are more likely to be successful. And, and so while it’s easier to do it when you’re younger, it’s more likely you’re going to be successful when you’re older.

Peter:

Yeah, it’s interesting. My 14 year old daughter has decided she wants to start a pajama company made out of recycled bottles. So like take the recycled bottles and like environmentally friendly, create, you know, buy the thread from people who do that and creeper John Cody and you know, she’s come to me for advice and you know, the advice I would give a 50 year old or 30 year old even would be like, let’s create a business plan about, and what I said to her is, yeah, here are the components of a business plan. These are the things to think about, but don’t think too much about them. Like don’t like, because you could get yourself so caught up in the complexity of it that you give up before you’ve even started. So like,

Chip:

Yeah, that describes my situation because I did have a business plan and I’d gone to Stanford business school. But to be honest with you, I was just so passionate about the idea of creating a rock and roll hotel in San Francisco where all my friends could go and stay and, and like hang out with all the bands coming through town. I didn’t really think too much beyond that, but it turned out it was a good idea. I, and it became a success against all odds. And so I agree. I think being passionate and purposeful pretty important. You also need to make sure you’ve got enough money to, to those first year or two when it’s frankly you’re starting out, it’s usually difficult. So I think I had enough money in the bank to make it work.

Peter:

Did you get investors? Does not really a venture capital thing both back then and, and the kind of business –

Chip:

I raised one point $1 million. It was bizarre to have a 44 room hotel in San Francisco and the total investment was one point $1 million to buy. The hotel actually was on a 40 year Landlease so I didn’t have to enough to buy the land. So it was a 40 year Landlease bought the hotel, renovated it, and reopened for the cost of a studio condo, if you’re lucky in San Francisco today.

Peter:

Wow. And this was in 85. Am I right? Is that…?

Chip:

87.

Peter:

87. Wow. So it’s not even like the, yeah, I mean obviously real estate prices were very, very different, but it’s not like the dollar was so, you know, it’s not like you did this in 1930 you know, after the crash revenue was like I’d be an elderly elder. Yes. It’s really amazing. Okay. So I’m curious about during that 24 year period of where you were CEO and, and running the company, this is a silly question I’m going to say, where are you as equally passionate and, and, and, and I’m asking this question because I think there is something about doing something in our twenties where we have incredible vision and passion and excitement and willingness to take risks. And I think that begins to add a little bit for a lot of people as they continue to, you know, run their businesses or work in their businesses or do, you know, lead and, and it’s, you know, one of the big challenges I think is to have people with experience who are equally passionate as they are experienced. And I’m curious what that journey was for you over the 24 years.

Chip:

It’s interesting. I’m a big fan of Abraham Maslow who spent some time at SPS limb Institute and wrote a book called P Calgary companies get their mojo from Maslow. And I believe that you can look at work in the form of a pyramid, sort of like his hierarchy of needs at the base of the pyramid would be a job. And then there’d be a career in the middle. And then a calling at the top. My job, my work at at Jordan Eve as the founder and CEO for 22 of the 24 years was a call. Like I was focused on the meaning and the inspiration. And it was very transformative for me.

Peter:

And let’s pause that. And actually before you get to the next piece, let’s pause there because I’m worried how for 22 years you can maintain that element of calling amidst the challenges and the obstacles and the, you know, headwinds and also obviously the, the opportunities and the rewards. Like did, did you, did you cultivate that calling? Did it, was it just there for you?

Chip:

The, the goodness is that the calling had multiple elements to it. So it wasn’t a singular thing. Yeah. I loved creating hotels and having each one have its own personality and its own name. And that was part of it. But I also loved creating a culture. I loved being the leader and the person who is very focused on how do we create a really dynamic culture that creative, enthusiastic employees. Because in the, in the, in the hotel business or the hospitality business, you know that if you have happy employees, you’re going to have happy customers. And if you call your companies Joie de Vivre, which means “joy of life” in French, you better… You’ve got to be trading in joy with, with your boys and your customers. So there was all of that. So it was not just a singular thing. I think we’re, you know, and in the bad times, like the.com bust, my point of view was like, what am I gonna learn from this? So, but there was a point when I was going, when we as a company were going into the great recession, and I was frankly moving from a place where it was starting to be a calling to going down to being a job, that everything that could go wrong did go wrong. The great came along. We were doing our greatest growth period during a very difficult time. I had a couple of friends commit suicide, which was not easy. And then I had a broken ankle and a bacterial infection in my leg and I was on a strong antibiotic.

Chip:

And while I was on the book tour for peak, I’m on crutches on antibiotics. At the end of the speech, I was sitting and signing books and I went unconscious. And and ultimately I went flatline at the point when the paramedics showed up and over the next 90 minutes I kept going flat line. So it’s almost like my body was giving me this little hotelier, a hope, a wake up call. The wake up call was like, chip, you don’t want to do this anymore. But I felt an exceptional obligation. I felt almost like I was in handcuffs, invisible handcuffs that said this is the thing you’re supposed to do. And I felt such a sense of obligation and responsibility. I, I think I, in fact, I had been even dreaming about cancer and car crashes. I had been, I really had been thinking, what’s the way that I could, I could give myself the excuse to no longer do this.

Chip:

And it turns out a, an an a, an allergic reaction to my antibiotic was what woke me up to realizing I need to sell this company even though we’re in the worst, worst recession since the great depression. It was not the right time to sell from a financial perspective, but it was absolutely the time to sell from a, an emotional perspective. So I had to have the emotional courage to both strip away the identity that defined me, which was for 24 years being a successful hotel, you’re an entrepreneur and an ma and really mommy and daddy because there were 3,500 employees at that point. And I was, and, and so I got a lot of identity from that. But I also realized it was, it was, it was a, almost like a life sentence to being in prison. There’s a famous Shakespeare quote, which is th one of the most unfortunate experiences for someone is to realize that there’s a prison that they don’t realize that they’re in. And so for me, I realized the prison I was in, and that’s when it went to being a job. And when a calling goes to being a job, the anesthetic wears off, you know?

Peter:

Yeah.

Chip:

Yeah. When you, when you’re doing your calling, you can jump over buildings in a single bound and, and, and, you know, you’re willing to do things that the average person would find maybe painful. And that, and everything became painful. Al all of a sudden

Peter:

Um you know, I, I was just in a conversation with a colleague of mine [inaudible] someone who is doing a bunch of work on conscious capitalism right now, but she’s a physician and she talked to me about these five questions that she asks or asked when she was really practicing physician. She might still be after AF, you know, like when she’s in the hospital with them the next day kind of thing, and they’re going to be in the hospital for another day and it can be 24 hours until she sees them again. And she gives them homework. And the homework, which you’ve just sort of, you sort of did in that moment was you ask them these five questions, why this right? Like, why did you get sick in this particular way? Why now? Right? What might you have missed? What else needs to be healed?

Peter:

And what is your heart saying?

Chip:

Wow, that’s beautiful. That’s beautiful.

Peter:

Isn’t it beautiful? And it’s, it’s like for all of us. And, and, and so here’s my, here, I have a question for you. I want some advice for me. So I, between the ages, I had 50 and I’m 52 and all sorts of things, little things, not big things, but things have happened. Like I got the shingle shot right in order to the vaccine. And a week later I got a full blown case of shingles. And they say it’s impossible. They said, there’s no way it’s a dead vaccine. My brother, who’s a physician says it’s total coincidence, but it’s quite a coincidence. But anyway, I got shingles then I was on my bike, I got in a bike accident, I went head first into a parked car, but it, but it was, you know and, and my, my body hasn’t quite felt like things aren’t working exactly right.

Peter:

Like my, the right side of my body. I’m sort of now doing physical therapy, but it feels like for a while there’s been a certain unease that’s been growing in me that is not at all displeased with what I’m doing, but feels like there’s something bigger and deeper that I’m moving towards. And I hear your story and I think that’s an [inaudible] event that you had, right? I mean, people ignore that event all the time, by the way, but it’s like, it’s, you know, it’s like you’re, you flatlined and it’s hard at that point not to go, Whoa, what’s going on? Even though you could argue, like, you could just say, well, I had an allergic reaction when I bought it. That’s what went on, right. There’s no reason to question anything, but you take it as an opportunity to question and, and you’re looking at your life and you’re saying, this is now I’ve, I’ve realized untenable.

Peter:

And, and I had, you know, I’ve, I Jim McCalvi was just on the show who was the cofounder of square and he talked about a similar event. And, and I think for myself, I’m not in that place, so I’m not, and I think there’s a lot of people like me who are not in that place. I’m not in the place where I throw up my arms and go, this is not working. Thank God. I have like, you know, a family that I love and great kids and I love my work and you know, I’m, I have enough. But there is still a sense enough dissatisfaction to say there’s something deeper here. I’m not touching on. And my question is, how do you, what’s your advice for people who have not hit like a low in that way but still need the emotional courage? Like the, like there’s stuff I’m going to have to feel if I say I’m going to take some risks and go and speak more from my heart than my head for example. Even though my head’s worked for a while, I’m still working and, and so there’s a risk to saying I’m gonna I’m going to move in that direction. And I’m just curious if you have thoughts about it based on your experience or based on all that you know.

Chip:

Well, based on my experience and also based upon what we’re seeing at the modern elder Academy I, I think that most of us who have a hard time with our emotions try to outrun them. They, they, they, well either try to outrun them or try to distract them. Those are, those are the two most common ways to do it. Out running them. B means that you’re just you, you, you just, you become a do-aholic. It could be workaholic, but it’s really just a do-aholic you have a to do list and it does. And that’s what you focus on. The other forms of distractions that people use are all kinds of addictions and all kinds of other things that they do. Those they’re also doing oriented, but they’re less focused on productivity. That that first one is like the outrunning your emotions speaks to the idea of, okay, if I perform, if I go out and do all of these things, maybe those emotions will go away.

Chip:

And the second piece is like, okay, well I’m just going to, you know, distract myself and maybe those emotions will go away. So what I can say confidently based upon personal experience, but also based upon the fact that we now have had 750 people go through the modern elder Academy. And it’s that allowing yourself the space for the emotions to catch up with you and then to be in a place where you can process them and make sense of what, what it, what, what is, how is serendipity trying to have her way with you in terms of showing you a bunch of little indicators and coincidences that are meant to be breadcrumbs for where you’re supposed to go next. And but, but to try to do that alone is hard. And so whether you’re in therapy or with a coach or whether you’re doing it in a workshop or you know, our program is a, you know, much more in depth program than say just a week and workshop.

Chip:

It’s, it’s a week long program, but it goes, it moves into the future as well. There’s an element that people, the thing that’s really interesting about all this, Peter, can I riff for a moment here, please? Yep. Okay. So here’s the thing. There’s been, there were three life stages that were introduced in the 20th century. The first one was adolescence. It didn’t exist before that. It did exist, but we didn’t have a word for it. And so adolescence got created in 1904 by Stanley hall, the president of the American psychological association. And he said, there’s, it’s a, basically a liminal period, an interstitial period between childhood and adulthood. It’s your preparatory stage and you go through emotional and hormonal changes during that time. And once that was discovered, society said, okay, let’s give these people who are 12 to 18 years old proper schools and tools like public junior high schools and high schools to prepare them for adulthood.

Chip:

Great. The second one is retirement. That was a 20th century phenomenon. We realized, okay people, you know, especially with people doing backbreaking industrial work, they need to like retire by 65 or or earlier and they need a pension and then need social security and okay, let’s give them something. And they, and we did the third, the third life stage of the 20th century that got created was midlife and all it has is a bad brand midlife crisis. Exactly. We’ve done zero. And that with the term midlife crisis is 55 years old. It was created in 1965 midlife is a new, a new era, partly because longevity in the United States was 99 I was 47 years old in 1,977 years old in year 2000 so midlife became a new thing. But we’ve done very little to help that. So this is a great segue to say, listen, what we need more of is for people in Asia, especially ages, well, midlife used to be considered 45 to 65 or 40 to 60, depending upon who you listen to today.

Chip:

I think midlife is 35 to 75 because in many industries it’s happening. People feel a little irrelevant earlier and a lot of people are actually working longer. So what we need is these midlife wisdom schools. We need these places where people go to imagine how to repurpose themselves and and mine their mastery and figure out if there’s a bunch of coincidences happening in your life as are happening to you right now, Peter, that you can try to make sense of them and then help with a, with a group of people to help figure out what’s next. I’m a big believer that wisdom is not taught, it’s shared. So actually being in a in our case at the MEA, modern elder Academy, 16 to 20 people in your cohort who are, they’re going through their midlife transitions you can learn so much from each other.

Peter:

How do you discern from this is a wake up call to like versus this was an allergic reaction to an antibiotic, you know, this is like how do you, how do you take the leap of faith that there’s a message for you in this versus, you know, you broke your leg or you, you know, like that stuff happens?

Chip:

You see the trend line. If there’s a trend line, if it’s a singular, if it’s a singular thing, maybe not. But for me I could see the trend line and the trend line for me was like, wow, I hate my job. I used to, I used to love, you know, going into the office on Monday morning. No I do not at all and that, and there’s a bunch of other things that I can point to to say like, there’s a trendline here. I’m supposed to have this wake up call. So I think being able to sort of understand what’s going on for yourself and trying to understand how much of it’s specific to situational or circumstantial situations as circumstantial factors or how much of it’s other, you know, someone could be going through a depression and if you’re going through an emotional depression, everything looks pretty bleak, right?

Chip:

And so does that mean you change everything? Not necessarily. If, if, if it’s if it’s something that’s somewhat more comprehensive, then it’s important to sort of understand what’s behind that. It may, it may be a childhood trauma that has you, that somehow got triggered and you’re in that state. And so the solution for you is not to try not to like change everything. In fact, in many cases, midlife crisis, the reaction people have to it is to go buy a Ferrari and have an affair. And you know, that’s for men and for women, you know, I don’t know. What’s that, you know, women don’t talk about their affairs as much as men do. Men, you know, men have to like show them off. So all I know is this, is that, you know, making change in your life if you’re doing it too, sometimes they make change as a way of running away from our emotions as well. And sometimes, sometimes the change is meant to, we think that everything’s going to change, but we bring our emotional baggage to where we’re going.

Peter:

Right? Wherever you go, there you are.

Chip:

Yup. So there’s that. There’s that, there’s this, I, I, I can’t say, I can’t tell you, you know, is there a pill you can take that just says, Oh, it’s gonna that will tell you whether this is an indicator of change or not. But what I can say is that there are great people, coaches and therapists and workshop leaders who can really be helpful for, for you to maybe translate, you know, here’s the thing that’s also true. Friends can be helpful. We’re not very good at being able to see our own signals and therefore, but we’re really good with our friends. Right? This is sort of a universal universal situation. So how can you create some emotional insurance in your life? Right now we have, we have property and liability insurance for a rainy day. But especially men, we don’t think of having an emotional insurance. Meaning who are the people you go to to look for some wisdom when you have a situation that is hard for you to decipher.

Peter:

And I think one of the challenges is to go to people who are not approaching your issues from their perspective, but they’re able to hold their perspective and approach your issue from your perspective. Meaning they can, they can share their perspective. But a lot of times people will ask you to do what will make them comfortable. And I think there’s, there’s a sense, and you know, there’s something else that I’m hearing from you too, which is and tell me if you think this is true, but there’s a level of certainty that you might like to have in a transition that doesn’t exist. And so the answer in part is you may not know, like, like you may not know. And so you, you don’t drop everything and go live a different life, but you start to make some moves that begin to explore something so that you could have, and I think to do that, and this really goes to your, your to do list, which I totally resonate with this, this, this addiction to checking things off the list, which is we have to slow down enough to let our feelings catch up to us.

Peter:

We have to maybe, you know, someone said to me who does alcoholics anonymous, so I’m not going to mention their name, but they said you know, if you want to know why you drink, stop drinking, right? Like you’re not going to know why you like your drinking in order to cover something up so you’re not gonna be able to figure it out while you’re drinking. So if you really want to figure it out, then stop drinking and see what comes up because whatever comes up, that’s why whatever comes up that you’re uncomfortable with, that’s why you’re drinking. And I think it’s the same for our addiction to speed and to, to do. And I don’t mean speed isn’t drugs, but like moving fast and to do lists. And I think we have to slow down enough and then, and then let whatever feelings come up. Am I providing value? Am I having an impact? Am I, you know, when we’re not moving and then, and then notice what comes up. And then we learn about ourselves.

Chip:

You know, it’s interesting, there’s a, a word that I learned over the last few years called liminal to be limital is to be in between two things. It’s a transitional space. And when we’re in puberty, we know an adolescence, we know that’s a liminal period, but there’s a new, there’s a relatively new word called middle essence. Middle essence is the adult corollary to adolescence. It’s when you go through emotional and hormonal changes around age 50. For men and women, women’s are more obvious because they have menopause. Men have something called andropause. And so we go through these, but we don’t really have a comp roadmap for what to do with this. Right. And Dan Gilbert’s Ted talk in which he was able to show that people at every age range from 20 to 90. Vastly underestimate how much change they’re going to have in the next 10 years is a very, is a very telling study because it means that we tend to get very comfortable, especially as we get older that our most of our changes behind this. And therefore we don’t like liminality we don’t like transitional times because it sort of came as a surprise. And in fact on the other side of that transitional space, maybe something that’s a huge gift to you that you didn’t even know you were going to be receiving.

Peter:

I love that Chip and I, and I, I think this you know, I, I remember reading some research about accidents that the reason most car accidents happen is because someone looks away for six seconds and you know, six seconds or, or more or something. I can’t remember what the exact number is. But the reason they feel comfortable looking away is because they see what’s happening in front of them. And they assume when they look away, whatever’s happening in front is going to continue to be at. So if there’s certain distance from the car in front, they keep going in the same speed. They assume whatever’s happening now is going to continue happening for the next six seconds. And that kills people because that’s the texting, right? Right. So they’re texting, they look away and they text and something changes in front of them and they can’t respond to react to it cause they’re not paying attention. And arguably we do that our whole lives. But you know, we look away for 10 years and, and so it’s, I find that interesting. So tell us about the elder Academy, the modern elder Academy.

Chip:

Well, let me tell you the background, how I even came to be, because like, the last thing I ever wanted to be called was an elder. I’ll be honest. So I, after I sold my company, I was 50 years old, wasn’t sure what was the next two years later, the three founders of Airbnb approached me and said, listen, we have this little tech startup and we want to be a hospital, a hospitality brand globally someday, will you help us democratize hospitality and join us as our in house mentor and our head of global hospitality and strategy. So I did, but what I learned like the first week was like, wow, I’m 52 and the average age is 26. And I felt old and I didn’t, I’d never worked in a tech company before. Felt completely out of my element and out of my perfect habitat. And I realized pretty quickly that while I was supposed to come in and be the mentor, I was as much the intern as I was the mentor because I was learning an industry I didn’t know anything about.

Peter:

Was that movie with Robert de Niro called the intern? Was that modeled after you?

Chip:

Well, it was like the exact opposite. Robert DeNiro came in as the intern and became the mentor to Anne Hathaway. Half his age. I came in as the mentor and became the intern, uh to Brian Chesky was 21 years younger than me. So, and my boss, but long story short is I learned pretty quickly that and they call started calling me the modern elder and they said that the modern elder is curious and wise. He’s not just he or she’s not just wise. And I was like, Oh, that’s interesting. I am curious, I, I’ve always been curious and in this place I better be curious because otherwise I’d be full of fear because I was realizing that I was frankly the dumbest person in the room a lot. But sometimes it was my questions that were rather innocent, that catalytic questions that showed a bro a blind spot that actually helped the company see things that nobody else has seen. So what this led me to was after four years of full time work there, and now three years as a strategic advisors, about three years ago, I said, okay, I’m leaving at fulltime role. I’m going to write this book called wisdom at work, the making of a modern elder, because I, what I see is there’s a, that we’re going to live longer, but power in a digital society seems to be moving younger and the world is changing faster. And those three variables living longer, power, moving younger, the world changing faster has a lot of people feeling irrelevant and confused and especially in middle life. And so in the process of interviewing people for the book, what became very clear to me is that we don’t have schools and tools for middle essence. We have them for adolescents created, you know, a hundred years ago. But now it’s time for us to realize that there are a lot of people who are in their forties or 50s or 60s, and they want to continue to be relevant, but they’re not sure where to go to actually repurpose their wisdom and shift their mindset about aging.

Chip:

Because there’s something called the U curve of happiness and, and you’re just at the end of the bottom of that curve. So the U curve of happiness shows that you know, between about age 25 and about 47 to 52 people go to in a long slow decline of happiness and around 47 to 52 but you’re pretty much 47 to 50 people sort of hit bottom on average. This is across all cultures. It’s been studied across the world. And then people tend to be happier in their fifties and forties happier in their sixties and fifties, happier in their seventies, sixties. Why the why is very interesting. The Y has to do with a few things. Number one is there’s the mashup of responsibilities and identities that people get tired of carrying all the baggage. So it’s like the first half of our life was about accumulating, accumulating roles and responsibilities and children and stuff.

Chip:

So that by your late forties, you feel like you’re carrying a huge load. And midlife is a marathon. So trying to run a marathon while you’re, you have all of these identities packed, you know, on your back means that you have to do your great midlife edit. And this is something we do at the Academy, the great midlife edit, which is basically saying what’s no longer serving you? What mindsets, identities, responsibilities, you know, ways of being are you ready to let go of and move on from? And it’s not because we’re saying, okay, everybody should leave their family or anything like that. No. To be honest with you, the number one thing that people tend to need to let go of our mindsets that are actually holding them back. And so, so that’s so, so that’s really a part of it. The other thing that happens is people do what Brenae Brown calls the great midlife unraveling and they actually sort of realize that it’s time to rejigger expectations.

Chip:

If disappointment equals expectations minus reality, and by 50 years old you can sort of see your reality and you can sort of see the future. You’re not going to be president of the United States. You didn’t marry your soulmate, your kids are not perfect. You’re, you’re not gonna make as much money as you thought. Okay. It’s time to actually rejig your, those expectations, but also to actually realize what is it that you have some gratitude about that actually is, you know, is actually serving you. And what’s curious is that as you get older, you start feeling more gratitude. Now this is, I know, I know, we know grumpy uncles and parents and things like that. And so there’s obviously people who don’t fit the profile, but the studies around the U curve of happiness are so widespread at this point. The research is so consistent that it’s, it’s a thing.

Peter:

Right. You know, it’s also interesting because Dan Arielli has done some research around actually very interesting research with people who had colostomy bags, right? Which is like not a pleasant experience at all. And he went to people, they looked at people who had, whose happiness levels of people who had permanent colostomy bags versus people who had the possibility in six months of having them removed meeting like that, that it was like possibly temporary and your intestines would be working again and you wouldn’t need to have a colostomy bag anymore. And the happiness, you would think that the happiness levels of people who had temporary colostomy bags would be higher because they had the potential to go back to a normal life. But the answer is it was much higher in the people who had permanent. And it’s because they, they, it was because uncertainty is what’s so concerning, you know, rather than the new reality which they can get adjusted to. And so in some ways, what you’re describing is you’ve gone through this period.

Peter:

Yes, it might be depressing to give up being president, but now that’s no longer on the table. You know, unless you’re in your eighties and running for president, it’s generally no longer on the table. And so you, you take things off and you’re in some ways reducing some uncertainty in your life because your options are narrowing. And, and like in the one hand you can look at that and say, that’s not a good thing. But on the other hand, it means that we’ve got more clarity about what’s going to happen. And again, you know, we’re, we’re not. So Dan Gilbert’s research says that we fool ourselves into thinking we know what the next 10 years are going to like and we’re really wrong. Or really have no idea, but, but I, but I wonder whether the certainty, uncertainty piece has a play in this.

Chip:

You know, I, my last book before wisdom at work was called emotional equations. It’s 18 different equations. So like mathematical mantra is about your emotions. And I did research on all of it. And anxiety has two primary elements to it. It’s, it’s uncertainty and powerlessness. And if, and it’s a, but it’s not a plus sign. It’s a times sign. So anxiety times powerlessness. So if you can actually bring one of those down to close to zero, then the fact that the other one’s high actually is, is salt. And what you’re just talking about there with the colostomy bag is totally this. So person who knows permanently, they’re going to cost me back. It doesn’t have anxiety because they don’t have uncertainty anymore. They may have some powerlessness around it, but there’s not exact, they may have some other things that, you know, but it’s not anxiety that they’re going to have and anxiety. When you have a combination of both uncertainty and powerlessness, which is the person who, who frankly has the temporary one, it actually inflames the anxiety. And so, yeah, I mean, I love what you’re doing, Peter, because I’m helping people become more emotionally fluid is something we should teach in junior high school. But for some reason we don’t. Instead, instead, our teachers or our parents who aren’t necessarily, they weren’t taught very well themselves.

Peter:

Well and I actually think it gets harder as we get older because we sort of, you know, there’s a way in which when we’re adolescents we’re trying to save face, but there’s also a sort of naivete of not saving face and there’s a way in which as we get older we feel like there’s more, you know, we’re, there’s more face to save. You know, there’s more like we have to show up and mask much more than, than we actually then is really true I think. And so it takes more courage to do that.

Chip:

This is masculinity, right? All about the mask.

Peter:

Right. Chip, it is such a pleasure to speak with you. I will. Here’s my plan. My plan is you’re here, here, here’s why nudge you. My plan is for you to invite me to come to a modern elder Academy that I come. You are invited and I would like to have you back on the show. So I’d like to have the experience and then I’d like to cause I know it would, I’m super excited for it. And then I want to be able to sit down and maybe even for a special episode of the podcast a little longer and to really unpack some of this stuff and, and explore it even more deeply because it’s a, I think it’s such an important conversation that you’re, that you’re sort of setting up and leading and supporting and facilitating and and just really, really important. And I think there’s also this opportunity that we have at our age to be brave and to say, look like we don’t have unlimited time in front of us. Like, we’re not dying tomorrow, please God, but we don’t have unlimited time and let’s not waste what we have. Let’s get serious about this and show up fully with all that we have. So I’m really excited that you’re, that you’ve started this conversation, that you’re facilitating the conversation and I’m excited to be part of it. Thank you Chip so much for being on the Bregman leadership podcast.

Chip:

Thank you, Peter. I look forward to seeing you in Baja.

 

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