Chip Conley: Founder and CEO at Modern Elder Academy (MEA), NYT Best-Selling Author, Speaker

In this episode Chip Conley, entrepreneur and founder of the Modern Elder Academy (MEA), shares his journey about creating a successful boutique hotel company to becoming a strategic advisor at Airbnb. 

Conley discusses the transformative experience of embracing midlife, a phase he sees as an opportunity for growth and learning, challenging the traditional narrative of a midlife crisis. He introduces the concept of the "wisdom economy," emphasizing the value of accumulating and sharing life lessons and experiences. 

Conley's insights on wisdom at work highlight the importance of intergenerational collaboration in the modern workplace. He advocates for a shift in mindset where midlife is viewed as a period rich with potential for reinvention and contribution. The conversation also covers the role of coaching in facilitating these transitions. 

Conley shares his perspective on how coaches can guide individuals through the challenges and opportunities of midlife, offering support in navigating personal and professional changes.

The episode also touches on the founding of MEA, a learning community focused on empowering people in midlife to redefine their purpose and contribution. Conley's passion for this initiative shines through as he discusses the academy's role in providing the tools and space for midlife transformation.

Transcript

Coaches on Zoom Drinking Coffee
Chip Conley

(interview blurb)

Chip: To unravel means you start to actually recalibrate what’s important in your life and what you are looking for from your life.

(intro)

Alex: Hi, I’m Alex Pascal, CEO of Coaching.com, and this is Coaches on Zoom Drinking Coffee. My guest today is a legendary entrepreneur. He was the founder and CEO of Joie de Vivre Hospitality, former head of Global Hospitality and Strategy at Airbnb, and founder of MEA, the world’s first midlife wisdom school. He’s a NEW YORK TIMES bestselling author and has written seven books, with his latest work being Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, set to be released in January 2024. Please welcome Chip Conley.

(Interview)

Alex: Hi, Chip.

Chip: Hello, Alex. It’s good to be here with you.

Alex: It’s always good to see you. Thank you so much for joining me in this episode of Coaches on Zoom Drinking Coffee today.

Chip: Yeah. And what are we drinking? 

Alex: Yeah, what are we drinking?

Chip: I have ginger beer. It’s got a kick to it. 

Alex: Oh, nice. I am close to my selection of kickers here so I may just join you, but I was looking for ginger beer at Bristol Farms this morning. I don’t know why they didn’t have some. So I’m drinking sparkling yuzu, which is actually delicious. 

Chip: Good. Good, good. Good. 

Alex: And I do have tequila and a Mezcal right there.

Chip: If our conversation goes a little crazy, you can always do a little shot.

Alex: Well, yours has a little kick. What kick does it have? 

Chip: There’s no kick of alcohol, I’m sorry. It’s just got a little — ginger beer, I used to go visit a friend in Jamaica, she lives with me now, her name is Cookie, and whenever you go to Jamaica, I just loved having the ginger beer there. My first restaurant I ever created was a Jamaican restaurant and so it was called Miss Pearl’s Jam House in San Francisco. But we’ll get into that.

Alex: Cool. Well, we’re both sharing fizzy, sparkly drinks. Mine won’t have any kick of alcohol either. But I was in Mexico this weekend and had a lot of spicy stuff, which is always great, and I know you spend a lot of time in Mexico but we’ll get to that. Before we get to that, I mean, you are an iconic entrepreneur, you’ve been in hospitality, you were part of a fast growing world changing startup that became a grown up pretty quickly, and now you’re heading MEA, which we’ll talk all about, just an incredibly exciting project, which leads you to spend a lot of time in Mexico so I am very excited to hear your story. I heard your story for the first time about 10, maybe 10 plus years ago at the Society of Consulting Psychology —

Chip: You mean when you were in high school?

Alex: Yeah, when I was in high school, and I went to that conference in Vegas. Yeah, right. Yeah, no, unfortunately, no. I’m actually a candidate for MEA to go through the programs now, which is exciting. It’s an exciting phase of life. I’ll be 40 next year so we’ll talk about that, maybe off the podcast later. We’ll see. I remember I heard your story, you were one of the keynotes, and it’s fascinating because you’re an incredible entrepreneur but even then before what you’re doing now with MEA, you’ve always had this greater vision for what you do and how you connect it to a lot of different essential aspects of being human so that definitely, it was very appealing to me. So, over a decade later, we’re sitting here having this conversation so I’m excited to rehash that story of Chip Conley and connect it to the incredible work that you’re doing these days.

Chip: For those who are watching, listening, I’ll give you some understanding of who I am. I grew up in Southern California, went up to Northern California for college and graduate school at Stanford. And a couple years out of Stanford Business School, I started a boutique hotel company in the mid 1980s when nobody had ever heard of boutique hotels and I was one of the first to do it and I called the company Joie de Vivre, which is a terrible name. It’s a lovely name in the sense it means joy of life and I like the fact that our mission statement was also the name of the company, but it’s hard to spell, hard to pronounce, and most people don’t know what it means. And so every single one of our Joie de Vivre hotels had its own name, its own brand, and boutique hotels generally are smaller, designed, have good food and beverage operations, and all 52 of these boutique hotels I helped to create were in California. So I was the founder and CEO of that company for 24 years. In my late 20s, I really struggled. I had started writing some books. I think the book that you might have been talking about when you saw me speak was Peak: How Great Companies Get Their Mojo from Maslow. So I’ve been always interested in psychology and business. I think I’m a frustrated coach. I think there’s a part of me that would love to just understand the psychology of humans more. And so I applied that in the context of being a leader or a CEO. But I started to like writing books and giving speeches more than I did running my own company. And during the Great Recession, gosh, that was very punishing for so many industries but especially the hospitality industry with hotels, restaurants, and spas, and I had everything that could go wrong going wrong in my life, not just my business life, but my personal life, family life, etc. And I said, oh my gosh, midlife is a crisis, isn’t it? I now believe midlife is not a crisis, it’s a chrysalis, and I have a TED Talk that came out recently that actually speaks to why it’s a chrysalis, not a crisis. If you think of the caterpillar to butterfly journey, midlife for the butterfly is the chrysalis, that dark and gooey place where it’s very liminal but it’s also where the transformation happens. So I ended up having a flat line experience at age 47 that was an allergic reaction to an antibiotic but it was like a divine intervention and I said, “I’m not gonna do this anymore. I’m gonna really completely changed my life,” and I did, and I ultimately sold my boutique hotel company, which I thought I’d be running ’til I was 80, but I sold it around age 50, and changed a bunch of other things. And next thing I knew, I was like, oh, I’m in my 50s and what’s next? And I spent a couple years writing a book that became a New York Times bestseller called Emotional Equations, basically sorting through my experiences of my late 40s. I was fascinated by festivals too. I was on the board of Burning Man. So I created a website called 300 Best Festivals in the World, and so I went to 36 festivals in 16 countries in one year because I just want to do like the most interesting person in the world, I guess. It was fascinating. But I got a call at age 52 from a guy named Brian Chesky, who I’d never heard of, and he had a company that I didn’t know much about. It was 11 years ago, and the company was called Airbnb. Now, I was a hotelier and I didn’t know Airbnb much and almost none of my friends had never heard of it, because I’m a boomer. Now, if you’re a millennial back 11 years ago, you probably had heard about it because millennials flocked to Airbnb. But it was sort of a weird thing to my generation. So he said, “I want you to come help us democratize hospitality. We have a fast growing startup but none of us have any background in hospitality or travel or, frankly, in leadership or entrepreneurship, so will you help us?” And so, long story short, is after initially working for a few weeks part time, it was very clear that they needed me full time and so I basically cleared my calendar and just said, “Listen, I am gonna be here as your in-house mentor for the three founders,” and they said, “We want you to be the head of Global Hospitality and Strategy,” and that’s what I did. But I was in charge of really so many different things in the company. And after about a month, they said, “Chip, you are our modern elder,” and I said, “Oh my God, you’re making fun of my age,” and they said, “Well, a modern elder is someone who is as curious as they are wise, Chip, and you’re both a mentor and an intern, because at age 52, you joined us and you’d never worked in a tech company and you don’t understand tech lingo or millennial lingo so you’re willing to be the learner as much as you’re the teacher.” And that was true. And I really appreciated that they had seen me for that. And I ended up spending four years full time helping to guide their rocket ship and then another three and a half years taking the company up to its IPO when it became the most valuable hospitality company in the world. So what a journey that was. During that time, and this was really my 50s, core of my 50s, I saw many of my friends struggling with midlife. They were struggling with a lot of things. I had five male friends from age 42 to 52 take their own lives during the Great Recession. And they were struggling from financial issues, they were struggling with feeling irrelevant, feeling like a loser, like they never lived up to what they thought they wanted in their life. And so what I got really clear on is that, man, midlife is an era that has been not very well studied and we don’t give a lot of resources to people. So, while I was writing a book called Wisdom@Work: The Making of a Modern Elder, my experience at Airbnb, went on a run on the beach in Baja, where I had — Baja is in Mexico, for those who don’t know it, and it’s a beach — at a beachfront home, and, one day, I went for a run on the beach and I had a Baja aha. I had an epiphany. And that epiphany was why don’t we have midlife wisdom schools? Why don’t we have a place where people can reflect upon and reimagine and maybe repurpose themselves? Not just in their professional life, but maybe their personal life and any parts of their lives. So that’s how MEA, the Modern Elder Academy came about, and that was about six years ago and we’ve had now over 4,000 people from around the world from 44 countries come to Mexico to our program, week-long program, and now we’re opening a campus in Santa Fe, New Mexico. And just to finish up, I think really what’s interesting to me is that about 20 percent of the people who have come to MEA have been coaches. And some of them sometimes are coming as a coach for their own personal journey of saying, “Okay, I’m 50 years old, what does it mean to be in midlife?” Our four key pillars are how do we help people navigate transitions, how do we help them cultivate purpose, how do we help them own their wisdom, and then how do we help them reframe their relationship with aging? So a lot of coaches come for their own purposes but a lot more even come to help their midlife clients because if midlife by sociologists is now defined as 35 to 75, almost all of your clients are in midlife and, yet, there’s not really a lot of training for people, for coaches, or for any of us to understand what are the dynamics of what’s happening in midlife. And so that’s why we created MEA. And I’d say coaches are a midwife for midlife epiphanies. And so that’s part of the reason that we started hanging out with you, Alex, because with the Coaching.com community and with MEA, there’s lots of opportunities for us to collaborate.

Alex: Thank you, Chip, for sharing that incredible journey that you’ve been on. So many interesting parts of your life. I didn’t know that you were one of the founding members of Burning Man. That’s pretty interesting. 

Chip: Founding board member, yeah. Totally interesting. We can talk about that if you want to. Been a fascinating journey.

Alex: We’ll get to that, for sure, and I think it has some interesting correlates to the Bay Area and tech community and that part of your journey that you experienced when you were part of Airbnb. Do you remember the first time you heard about coaching throughout your career? Before this stage, when you were an entrepreneur, an entrepreneur in residence, what was your association of coaching? 

Chip: Well, I think one of the first associations was my best friend Vanda. She went to CTI, the Co-Active Training Institute, and she learned about what it means to become a coach, an executive coach, leadership coach, life coach. And when I was going through that really rough time in my late 40s, thank God she was there by my side. She used her friendship skills but she also used her coaching skills to help me to get to the other side of that chrysalis, that other side of that dark piece of my life at that time. So, definitely recognize that. When I had Joie de Vivre, we had 3,500 employees and so we would hire coaches for some of our people in the company and then we’d actually even train some of our in-house employees to become coaches. When I joined Airbnb, one of the first things I said to Brian is I said I’d like to help create coaches within the organization, because we were spending money for people outside the organization to come in, and that was fine and we still spent money on that, but what would it be like to actually take some of our coaches, some of our in-house people. We did an exercise. We asked the following question on an employee satisfaction survey, we asked everybody in the company who beyond your boss do you seek out for advice or wisdom when you need it within the company. And what that did was when people actually qualitatively answered that, we got a list of who was perceived as being wise in the company. And that was a really interesting experience, Alex, because it was my first opportunity to see like, wow, most companies do not measure wisdom in their company and we live in an — in the era of artificial intelligence, when knowledge has become commoditized, what we really need is wisdom and that’s what scares. And so we started to look at, at Airbnb, who were these people who were perceived as wise? What were the qualities that was common amongst them? And then we could start training around that and then we could start look at our maybe — we created a wisdom heat map on the org chart, where’s it showing up, in what departments, etc., and, ultimately, we went to a handful of the top 20 people who were perceived as being wise in the company and we asked them if they would like to train to become a coach and whether to do that in-house full time or part time. And about four or five people took us up on that. So coaching has been very meaningful to me for a long time. And when I started MEA, I didn’t think of the coaching element to that but it’s been clear now six years into it how many people look to me and say, “Chip, where did you get your coaching training?” and I say, “I’m driving without a license.” Because I’ve never done any formal training. I have certainly — I’m a big fan of the Hudson Institute and CTI and a whole collection of other programs but my training has really been on the job. As a coach slash CEO and then with Brian as a CEO whisperer, I’ve learned what it means to know the qualities of being a great coach. 

Alex: Absolutely. I mean, you’re not driving a car, you’re driving a bus because there’s so many people that you’re driving with MEA and the impact that you’re able to harness when you’re supporting the coaching community is incredible. It’s one of the things that appeals to me the most about the work that we do that coaches really are these incredible vessels of transformation and change and they help so many people and when you’re helping coaches become acquainted with different learning models, different approaches, methodologies, or a better understanding of, in your case, what this stage between 35 and 75 entails and really do a lot of good in the world. So, let’s zero in on the work that you’re doing at MEA and now we know how it came about, you have that difficult stage where it really did sound like the typical midlife crisis and then that recognition and recalibration of what midlife is, so what do you think people struggle so much through that phase? I’d love to learn more about that. And before you answer that, I’m actually — I’m thinking about 35 sounds a little early for the beginning of midlife so how does the realization that 35 as the beginning come about? Where did you pick that from?

Chip: Well, I picked it up from sociologists so it’s not just my thing, it’s a lot of sociologists now say that that’s the case. Why do they say it’s 35 to 75? In the past, midlife was considered 40 to 60 and then 40 to 65. So why has it expanded to be a marathon from 35 to 75? On the higher end, at 75, the reason for that is there’s a growing number of people who are becoming centenarians and so if you’re going to live to a hundred, then, yes, mid-70s could still be midlife. And there are a lot of people, huge growing population of people in their 70s, who are still working. And so often when someone is in that working phase of their life still, it can be considered midlife. So, that’s on the high end. On the low end, why 35? Well, in a world in which more and more people are feeling obsolescent in their jobs earlier because of technology, because of AI, the kinds of things that people are dealing with at 35 are the kinds of things that people dealt with at 45 a few years ago, when they started feeling irrelevant possibly at 45 or 50. So, sometimes, people feel irrelevant. If you’re a software engineer in Silicon Valley, you might feel irrelevant at 32. So, yeah, I think the core of midlife really, I’d say 45 to 65, so shave off 10 years on either end. And at 40, at your age, you’re sort of going into midlife, for sure. Forties are a tough decade so let’s get to the question. Why is it that people struggle with this? Why does the term “midlife crisis,” the worst brand ever attached to any life stage, why is it so resonant with people? 

Alex: Well, the terrible twos are also not great. 

Chip: That’s true. That’s not a life stage, that’s just one year of your life—

Alex: Exactly.

Chip: People who are telling you the terrible twos, you have no idea what they’re saying.

Alex: Exactly.

Chip: But when someone says to you you’re in your midlife crisis, like, “Oh, no. Is it that obvious?”

Alex: “Is it because I’m driving this new convertible?”

Chip: “And I’m dating my secretary?” I mean, that’s the male version. The female version has a lot of different forms it takes. It often takes the idea of being invisible. So what’s happening in midlife? I’d say the number one thing that, comes from my book, Emotional Equations, I’ll use an equation, it’s disappointment equals expectations minus reality. So let’s unpack that for a second. So, by your 40s, you sort of have built up a bunch of expectations about how your life is supposed to be. There may be hope. The difference between hope and expectations is that hope is — has a little bit of fate involved, a little bit of like a sense of like, “Hmm, okay, I would love to have that happen.” Expectation, on the other hand, is almost like entitlement. And so if you’re 45 years old and you do not have a net worth of a million dollars like you thought you would or you did not marry your soulmate, you married somebody who you don’t like a whole lot, or your kids are not like super successful in high school, all of a sudden, you sort of look at your life, it’s like, “Man, I’m disappointed,” because reality is not as good as expectations. And so what — Brené Brown is a friend of me and of an MEA, what she says is she calls this the midlife unraveling. And I when I first heard her say this, I said, “Brené, no one wants to unravel in midlife. I don’t think that’s a positive statement,” because unraveling makes you sound like you’re losing your mind, and she said, “Chip, have you ever looked in the dictionary under the word ‘ravel’? Ravel,” I was like, “No, I don’t —” and she said, “In the dictionary, something that’s raveled is something that so tightly wound you can’t get it undone,” and she said for a lot of people in their late 40s, they’re so tightly wound with their expectations, so tightly wound with what they thought they’re supposed to do, so tightly wound because they have a life full of spinning plates, because our late 40s is the time when we have very — we’re full of time poverty, not time affluence, because it’s a very busy time in our life, especially for sandwich generation, taking care of our parents, taking care of our kids. Long story short is to unravel means you start to actually recalibrate what’s important in your life and what you are looking for from your life. And it’s a hard process and, sometimes, it’s external circumstances that are thrust upon you. I mean, me having a flat line experience and me having a bunch of things not going well in my life in my late 40s. That sort of forced that reckoning. I call it the great midlife reckoning ball, because there’s a reckoning and it’s like a wrecking ball to your life. And yet, it’s the time where you start to actually take a step back, make sense of what’s important to you, and be able to say, “Listen, I have been living with a success script that my parents gave me or my community gave me or my first spouse gave me, and I don’t like that script anymore. I don’t wanna live by that script. I wanna actually create my own.” And that’s when life gets a little more interesting, because you start having some agency. And I just love it. I mean, at MEA, at the Modern Elder Academy, to see that many people sort of going through a period of their life — so a normal workshop has like 24 people in it. We’ve had people as young as 25 and as old as 88, average age is 54, and they all think that they’re the only one in the world going through what they’re going through right now and they’re like, “Oh, no, everybody’s going through something,” but the thing that’s really interesting is how many people just didn’t realize how many options they have available to them because they were sort of stuck in a routine and a habit and maybe with blinders of what was available to them and starting to realize how do you navigate transitions and cultivate purpose with more options available to you is incredibly liberating. And so I’m proud, because I lost five male friends to suicide 15 years ago and I would love to have had a program like this because if some of them had gone through this program, I doubt they would have gotten to the point where they felt like they had no options.

Alex: How did you go about assembling the team and creating the curriculum?

Chip: So there were a bunch of people who have done amazing academic work in this area. So I write books, my seventh book comes out soon in January called Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, but I’m not an academic so I am very reliant upon academics. And so whether it was Arthur Brooks at Harvard, whose book, From Strength to Strength, profiles MEA and tapping into what he knows, Becca Levy at Yale, whose research had shown that when people actually shift their mindset about aging from a negative to a positive, they gain seven and a half years of additional life. Dacher Keltner at UC Berkeley and his research on awe and especially in midlife, how do you reintegrate awe into your life. Carol Dweck at Stanford and her work on mindset, how you move from a fixed to a growth mindset. So what we did is we really reached out to a bunch of well-known academics and I’m lucky, I’ve spoken at the TED conference three times so even though I’m not an academic, I’m very connected to a lot of academics.

Alex: And you’re a great speaker, by the way. I love hearing you speak. 

Chip: Thank you. Thank you. And so I went out to Adam Grant, I went out to Dan Pink, poked Esther Perel, and then I pieced together with my team a curriculum that was fusing together social science evidence that helped us to have something to build a curriculum upon. So we’re not a retreat center like the Esalen Institute, which I love, I was on the board for 10 years there, or Omega on the East Coast of the US. Those are retreat centers and they have people come in and they do their thing and there’s a curation but there’s not a curriculum. And so, in our case, we have a curriculum, and so people come and they’re going through our program. Yes, we do have a lot of famous teachers like Esther Perel and Dan Buettner from Blue Zones and Michael Franti, the famous musician, but their material for the week is the icing on the cake. So, for me, it was a beautiful opportunity for me to be the geek that I like to be occasionally in terms of crafting a program that is dedicated to middlescence. Adolescence is a word that only became into the lexicon of mainstream until 1904 and once adolescence became a thing, everybody knew, like, “Oh, your teen years are this liminal stage, this transition stage between childhood and adulthood.” Well, middlescence is this adult stage between your adulthood and your early elder years. So I wanted to create a program that really dedicated to helping people understand what the roadmap is for this time of life. What’s the upside of aging? What’s the downside? And what can we do about it? And that’s why Blue Zones has been a great partner for us because their work focuses very much on what places in the world provide the greatest longevity and percentage of centenarians.

Alex: So is there a component on the program around health supplements, food?

Chip: There’s a little bit of a component on that but we’ve actually — it’s been interesting. There are so many programs out there about how to bio hack your aging.

Alex: Well, you’re in the Bay Area right now, that’s probably happening a lot.

Chip: And we didn’t really want to just be another program that’s focused on that. Do we focus on that? Yes, we do. And, of course, our Blue Zones, when we do Blue Zones workshops, very focused on that. But we wanted to look at the psychological and the emotional and even the spiritual side of getting older, and especially in your 50s. Forties, fifties, sixties are the core of this. And so that’s actually what we focus on. And we also focus on a whole collection of skills that we don’t often learn. If you’re a coach, you learn these things. You learn how to listen, how to active listen, how to do appreciative inquiry to create catalytic or generative questions. But if you believe that, actually, as Jimi Hendrix once said, knowledge speaks and wisdom listens, then learning how to be a great listener, which is what coaches do, and knowing how to craft a question that becomes catalytic to the person, that serves them, isn’t serving you, these are some of the skills that help people to understand how can I become a spectacular mentor or how can I look at where I want to take my life and tap into some of the wisdom I’ve learned. We live in an era that’s been the knowledge economy. We’re moving into an era that I think will be the wisdom economy, and what does that mean? It means that people have to learn how to metabolize their experience, because our painful life lessons are the raw material for our future wisdom. So I’ve been doing a practice since I was 28, so for 35 years now. Every weekend, I sit down and I make a set of bullet points of the key things I learned that week. So I did it this last weekend and I’ll come up with three, five, seven different things in my personal life, my professional life, just while it’s fresh in my mind to say like, “Ah, here’s what I learned. Here’s what happened. And here’s the key lesson and here’s how it’s gonna serve me moving forward.” I had no idea 35 years ago when I started to do this, the reason I did it originally was because I was an idiot 28-year-old CEO who didn’t know what I was doing running my company, but I came to realize that what I was doing was I was accelerating my wisdom. By actually looking at my lessons, I was actually in essence digesting or metabolizing everything that I was learning. And, sometimes, those lessons felt like they were punishment, but when I could actually see the punishment taught me something that’s going to help me moving forward. Viktor Frankl quite famously lived through the concentration camps and wrote the book, Man’s Search for Meaning, and that’s really what he says. He says the people who lived and lived to talk about their concentration camp experience were those who had a belief and were able to figure out a belief that they were going to be better as a result of this experience. Not that they’re trying to be Pollyanna, but that there was something good that was going to come through this and there’s going to be some meaning and some hope and some learning. And so if we can do that in our lives, thank God we are not living through concentration camps, but sometimes our life feels like a prison and so how do we help people with this? And this is like this is what a coach does, and this is why I love what you guys do. I love you guys as coaches and Coaching.com, specifically, because to help people make sense of their life experience and then use it moving forward, and then maybe share it with others. What an opportunity. I’ll tell you one last thought. So that idea of this wisdom book I’ve created, the bullet points, so I started introducing that to my senior leaders at Joie de Vivre, my boutique hotel company, at Airbnb, and then an MEA. And the idea was no one has to do this every weekend. No one has to do it every month. But once a quarter, you do have to do it. Once a quarter, you have to do an inventory of what was your biggest lesson of the quarter. And then we’ll have like, let’s say there’s a leadership team of eight people. Once a quarter, we come together as a group of eight of us and each of us say, “Here is my biggest lesson. Here’s what I learned from it. And here’s how it will serve me moving forward.” It gives people the opportunity to be candid and vulnerable but also to share wisdom. Wisdom is not taught, it’s shared. The best part of it is that at the end of the meeting, the eight of us in the meeting will say like, “Okay, what’s our biggest team lesson this quarter?” And our biggest team lesson is something that we can talk about, and it allows us to say like what’s working, what’s not as a team. So, let me just say that I just think for coaches who are doing coaches with executives and leaders and people in organizations, this is a beautiful and free and easy thing for anybody to do. 

Alex: You’ve touched upon so many very interesting things. One of the things that strikes me about your whole career is just the level of intentionality. You’re a young entrepreneur and you’re finding time to sit down and write your learning lessons. I mean, a lot of people just don’t do that. So they intentionality combined with that hunger for learning and the way to crystallize that in a methodology for execution is one of the things that I admire about your journey the most. It’s not easy to do. It’s not easy to execute and also be intentional at the same time.

Chip: Peter Drucker, I never met him but he was always somebody I admired, Peter Drucker wrote 40 management books and was sort of the father of modern management theory. He wrote —

Alex: And they’re big. When you see these books, they’re not just…

Chip: And he wrote, of those 40 books, he wrote two-thirds of them after the age of 65. He had a practice. His practice was every two years, he would learn a new subject that had nothing to do with being a business school professor or a management theorist or author. Could be Jap Japanese flower arranging or medieval word strategy. Because what he believed was being curious and open to learning something new is the ultimate lubrication of the brain and soul. It’s like the fountain of youth. And so he made it as a practice to say, “I’m just gonna go learn something new. I’m always gonna be a beginner at something.” And so I try to do the same thing. And it’s hard. For some people, there’s the mindset of like, “Oh, I’m too old to learn a language,” or, “I’m too old to learn surfing,” but I learned both of those at age 57. I’m 63 now. The question I like to ask and this is a question we asked at MEA to anybody in our cohorts is what do you know now or have you done now that you wish you’d known or done ten years ago, and then once you have that locked in your brain, ten years from now, what will you regret if you don’t learn it or do it now? And what I love about that question, the prospective question of the future, is it brings up the idea of anticipated regret. what will I regret if I don’t learn it or do it now? And I think anticipated regret is a form of wisdom. It creates a bit of a catalyst for you to say, “I’m gonna go do that now.” Because when I asked that question at age 57 and I was living on a beach in Mexico near a surf break, I was like, “Okay, well, it’ll be harder at 67 to learn to surf than at 57. It’ll be harder to learn Spanish than it is at 57,” and so that’s what led me to getting a burr in my saddle, as they say, to learn it.

Alex: Another thing that I find very interesting about, as you’re talking about your journey, your experience, in some of the findings of your research, which has been extensive, is the power of perception. I mean, that research finding that you mentioned about if you have a positive perspective about aging versus a negative perspective, you live, what? Like seven more years. Like that is —

Chip: Yeah.

Alex: It is incredible to think about how much our perspective can impact our life and other people as well. And when it comes to coaching is I think it is very important for coaches to be attentive to that. What’s their perspective when you’re looking at someone’s assessments, there’s so many aspects of coaching where it’s interesting to think about the coach’s own perspective and how that translates into the relationship with the client and having an undertone of an evaluation of what that perspective is and reframing, in some cases, when needed, because you can look at the same thing from two different perspectives. And perhaps one is more helpful than the other and I think that’s a lot of what we do in coaching sometimes. It’s we’re working with very high functioning people that are very successful and, oftentimes, a little push here, a little change of direction there can have an incredible change of perspective.

Chip: Well, the beautiful thing about a coach as opposed to a friend or family member or spouse is that, ideally, they don’t have a vested interest in forcing you to answer a certain way. Their job is to be a permissionary, to create permission for you to try something and maybe show more options, have that be a first class noticer, to notice things you don’t see in yourself. 

Alex: Totally. 

Chip: And, frankly, in listening to the client, notice for what’s not being said. The best coaches I know are not the ones who are noticing what’s being said, they’re the ones who notice what’s not being said. And that gets interesting. I think there’s two kinds of mentors in the world. In Airbnb, I mentored over 100 employees over the seven and a half years I was there, and I want to mention this because I think one of them is much more like a coach and one of them’s not but when you’re a mentor, you can either be a librarian or a confidant. And so let me explain. So librarian is the know-how and know-who. You go to a librarian in a library, back in the old days when I was going to libraries, and you ask them something and they take you to the bookshelf where you’d find it, but the best thing about a librarian was they knew things that you didn’t ask. You would like maybe to ask a question and they say, “Oh, well, here’s a white paper you should read,” or “Here’s an interview on 60 Minutes that you should watch.” And so when it comes to a mentor, often I was a mentor at Airbnb for people who wanted to ask me questions and my job was to answer them. And so my job was to transfer knowledge. And, sometimes, that’s what a mentor is. That’s really not a coach. That is purely somebody who’s got — they’re a subject matter expert and people want to tap into that. The second kind of mentor is really more of a coaching role and that’s the confidant. And I have a little story on this. There’s woman named Lisa Dubost, a 25-year-old employee at Airbnb, and she was in charge of learning and development and she was amazing, I loved her, and she had no background in this at all. And our head of HR had left and so I was helping her out. And she said to me one day, “Chip, you’re my confidant,” and I said to her, “Lisa, you have not given me any juicy details yet. I think of a confidant as someone who tells me secrets.” And she said, “No, in my part of France, where I’m from, a confidant is the one who gives you confidence.” And I think that’s a real beautiful statement for what a great coach does. 

Alex: I love that.

Chip: A coach will tell you the things you don’t necessarily want to hear. A coach will be that first class noticer to hold up a mirror to see things that you need to see. But a coach who’s worth their salt is somebody who is a permissionary, someone who believes in you and really pushes you to take risks, which is why it’s very different than a parenting role. And somebody who gives you a sense of confidence and helps you through the questions they ask, see the path that will get you there. Notice that the librarian relationship, it’s the mentee asking the librarian the question, whereas in the confidant relationship, it’s often the confidant, who’s the mentor or the coach, asking the mentee or the client the questions. And that’s when it gets interesting and that’s why appreciative inquiry and any forms of asking great questions is really an essential part of being a great coach,

Alex: You’re tapping into the balance of challenging and supporting and there has to be the right balance and coaches, oftentimes, adjust. Certain clients need to be challenged more and need less support, some need a lot more support and less challenge. So it is an interesting dynamic and one that needs to be adapted to the client because you can’t have a formula where, “I provide this much challenge and this much support,” it is really this dynamic relationship. I love that the meaning of confidant in France — and, by the way, I would tell you all my secrets but we’re recording this so you’re someone that I want to talk to and tell — be like use as a confidant, I can totally see how people are attracted to that with you, but we’ll hold that until we’re not recording a podcast episode. All my secrets. No, no, not ready for that.

Chip: I think the difference between a confidant and, let’s say, a confidant coach and a psychologist or a therapist is it’s rare for therapists to actually bring themselves, their personal life, their life into the conversation. Whereas with a coach, I actually think it’s quite helpful, because it both shows humility, it allows the client to actually understand that this is someone who’s not judging them because this coach has gone through their challenges. It’s another form of sharing wisdom. And so I highly recommend that coaches — of course, a coach, who actually starts to dominate the conversation, wanting to talk about themselves, that is not a good coach. That’s not intent. But the intent is to help the client understand that this person in front of you is wise and they’re wise because of their lessons. 

Alex: What are you excited about the most in the work that you’re doing today?

Chip: Well, I’m really excited about this new book, Learning to Love Midlife. I’m going to be on Good Morning America and the Today Show on the week that it comes out, which is interesting, I told you about this earlier, it’s the week that actually I stopped my radiation treatment. I have prostate cancer stage 3 and it spread to my pelvic lymph and so I am going through hormone depletion therapy right now, which means I basically have no testosterone. And I’m going through 36 different sessions of radiation every day, every weekday, so I’m a little tired right now as we’re talking. I probably don’t seem like entire because —

Alex: You don’t.

Chip: — I just have way too much energy. So I’m excited about the book coming out. And then I’m also a little cautious because what’s it going to be like, Friday the 12th January 12th, when I have my last radiation session, and on January 13th, I fly to New York, and January 15th in the morning I’m on Good Morning America and January 16th, the book comes out, January 17th, the Today Show and the New York Times and keep going. So there’s a lot. I’m also excited about MEA opening its campus in Santa Fe, New Mexico, a 2600-acre regenerative horse ranch, partly because being in Mexico, I love it. I love living in Mexico part time. But it’s not the US and the US is our primary market of people who come to MEA and so having something in the US, especially in a place as beloved as Santa Fe is, is great.

Alex: It’s still Mexico, it’s just the New Mexico.

Chip: It’s New Mexico. It does actually feel like — I mean, part of the reason we chose it is because it does feel a little bit like it’s not in the United States. Nothing wrong with the US, but the idea of being in a place that feels a little foreign is really valuable for doing our work. Our work is meant to help people transform and if you’re doing it sort of at the local mall or you’re driving one hour to a retreat center and then you can leave after one night by driving home if you don’t like it, that’s a different experience. We sort of — both of our locations in Baja as well as in Santa Fe, they require pilgrimages. You’re making the journey to a place and you’re making a commitment. It’s a place where your habits are being left behind so your habitat is really important in terms of changing your habits. So, long story short, those are the things I’m excited about. I’m also excited about my sons. I have sons who are 12 and 9 and they’re right at that age where I can feel that I want to and need to give even more time to them and that’s really meaningful to me because not only do I deeply love them but I had a foster son who is older than you, he’s 47 years old, and I became his foster — he’s African American, I became his dad, he moved in, I was 28, he was 13 at the time.

Alex: Wow. 

Chip: And it was a real struggle for many, many years as his father because basically he came into this lifetime with some challenging genes and a very troubled childhood, he ended up in a group youth home and I was his mentor and he asked me one day, “Will you be my dad?” and how can I say no to this kid. But when you have your own biological kids, you’re a little more control than when you basically take on a foster child at 13. And so I want to show them how much love they deserve.

Alex: Wow, Chip.

Chip: When are you having kids?

Alex: You’re making me feel like I probably should, pretty soon because, for me, it’s an integral part of life. I don’t want to be one of my regrets not having children. I’m 39, I’m going to be 40 pretty soon. I want to, it just needs — I think it comes at a different time for different people so I’m sure that in my first half of my 40s, I’ll probably figure that side of things that. As an entrepreneur, sometimes it’s hard to. You get so committed to what you’re doing. I don’t feel like I have the space for that at the moment. So maybe it’s a good excuse —

Chip: You will feel that way for a very long time, but you also have to be in a committed relationship with someone who wants to have children and it may be, in your case, it’s a woman and it may be somebody who does the tough work and she says, “I wanna have kids so let’s have kids,” and is true for many mothers, she has the harder job. I mean, the pregnancy, of course, but even the raising of kids, more and more, it’s split between, in a heterosexual couple, between a man and a woman, or the father and the mother, but, generally, it’s not split. Generally, you may be the hard driving entrepreneur and your partner wife may end up being the one who says, “Listen, Alex, I’ve got this. Here’s what you need to do as the father,” and she gives you your instructions and then you have that part of your life that allows you to do that. But children do not bring happiness, they do bring meaning. Let me explain that. This is basic principles of social science on this. Children often do not bring short-term happiness, unless you’re in a very reflective place where you’re — but, generally, they bring some short-term pain and difficulties. It can be very hard on a marriage or a relationship, but it does bring meaning, both short term and long term. And so, as we get older, again, back to the MEA curriculum, what gets more important as we get older is what brings us meaning. Family is a huge piece of that. And I’m not saying that people have to have kids, you could have two lovely dogs and that’s like that’s where the energy goes. Or you could be a mentor to a bunch of people and that’s where the energy goes. But Bob Waldinger at Harvard has been a friend of MEA and they have done at Harvard this adult longitudinal study for 85 years and what they’ve been able to show is — the same group of people over 85 years. Now, most of them are dead now because they started in their teens but what they’ve been able to show is the number one variable for older people who are living longer, happier, healthier lives, is how invested were they in their social relationships in their 50s. And so what happens for a lot of people, let’s talk about men versus women. Women are socialized to be much more open to being vulnerable and having friendships and, yes, there’s some narrowing of how many friendships they have as they go into the childbearing years and working hard, etc., but they somehow are able to juggle those, and certainly when they’re going through a hard time, go to friends and look for support. Men not so good. Men not as good at this. They’re number of friendships narrows over time. They don’t think of friendship as a practice or a muscle to be exercised, and so a lot of times men get to their early 50s and they have very few friends, the friends, they do have, they talked about Monday Night Football with and they don’t really get into any depth with them. And, frankly, they’re comparing their insides with other people’s outsides. And so it becomes a really awful situation that for a lot of men in their 50s, they feel a bit defective because they think they’re getting the Game of Life wrong. And so what I like to say to people, especially men who come to MEA, is this is the most important time in your life to actually learn how to invest in social relationships, what I call social wellness. So work on that, Alex. Work on that too. You have many things to work on, my friend.

Alex: I will keep you updated on that journey, for sure. And you opened up about the treatments that you’re going through for the prostate cancer and thank you for being open and sharing that very personal detail and process you’re going through. So, a number of people that are navigating their midlife will have experiences like this. So you clearly have an incredible positive attitude and incredible energy. How has this process been for you? I mean, I think a lot of us have this fear of, like I watched a lot of Curb Your Enthusiasm and Larry David always, anything happens and he thinks it’s cancer, and he’s like the level of stress and I always empathize with that, like something happens and you think, “Oh, I hope it’s not gonna be,” and the one day where you’re hoping something won’t be and it is, I’m sure it’s a vexing experience. So, tell me a little bit about the experience you’ve gone through. 

Chip: Yeah. Before I go into my personal story on this, let’s talk broadly. So there are a lot of transitions that are happening in midlife and one of them is a health diagnosis, but it’s your parents passing away, empty nest, menopause, men have something called andropause that they don’t even know they’re going through. 

Alex: I actually never heard about that. 

Chip: Yeah, andropause is the male version of menopause. Google it. What else? There’s changing careers, getting divorced, etc. So there’s a lot going on. And so we really help people at MEA to learn the three stages of the transition, the ending of something, the messy middle, and the beginning of something new, based upon William Bridges’s work and his book Transitions, and Joseph Campbell’s work with The Hero’s Journey. For me, I had to get really comfortable about five and a half years ago when I first had the initial signs of having a stage 1 prostate cancer diagnosis, I had to get comfortable, like, “Okay, all right, I better get used to this,” and then as it went to stage 2, I had to start getting used to the idea of something ending, because I could sort of feel like, again, if there’s three stages to a transition, the ending, the messy middle, the beginning, a stage 2 cancer diagnosis means that it’s growing in the prostate, it hasn’t gone outside the prostate yet but it does mean that I’m probably going to have to do some more serious surgery and before I had my prostate taken out two years earlier, I had another thing called HIFU and it’s something called ablation therapy and I basically lost half of my prostate in surgery and that meant that had some consequences in terms of my romantic life, my sexual life, and, frankly, how I felt a little bit. And I had to have a catheter for 10 days, etc. So, I started to get used to the idea that, “Oh, my gosh, I am going into an era of my life where I had to ritualize my relationship with my prostate.” And we won’t go into much detail on that because it has a certain function in a man’s life, but I had to ritualize, “Okay, this is the end of that era.” And, ultimately, it really got to the place of having my prostate taken out and then being in the messy middle. And now, I’m in the messy middle period right now and when you’re in the messy middle, things are painful, sometimes, emotionally, physically, whatever. And you feel a little awkward. And like right now I feel a little nauseous. So you get used to that. You actually — it’s the most important time of these three stages to be reaching out to friends and to have social support but it’s also the really important time and you can still see like, “Okay, on the other side of this, this is what I’m gonna learn from it.” It’s the through line. And it’s something that coach says, well, if they can actually help someone see the themes in their life and see like in the midst of what you’re going through, here’s the through line, here’s what you’re learning, and so I’m having a through line right now about what it means to go and really almost start feeling a little bit more like a monk, which is not the way I’ve been in the past. And then I’ll get to the other side of this, after this radiation and I really think I’m going to be the beginning of something new. And the beginning of something new for me will be sort of living a life that is less from testosterone prison, which is where I’ve been for a long time, meaning when you have testosterone prison, like sometimes the testosterone fuels your behavior in ways that it makes me feel like I’m sort of not liberated from it. I feel liberated from it right now and I think I will in the future, and I think that being able to get to the other side of this and to say like I am not just a cancer survivor but I’m someone who’s actually gone through five and a half years of two surgeries, hormone therapy, two catheters, catching COVID in the hospital when I had my prostate taken out. I mean, I have a story. And I have radiation and I have a whole collection of things that will allow me to get to the other side of this and say, “Here’s what I’ve learned.” So the way I look at cancer now is that cancer is my ultimate teacher. And so rather than it being my enemy, which is how a lot of people think of cancer, it’s like, “Okay, it’s a war. This is the Middle East, it’s a war, and we are at battle.” I don’t look at it that way. I look at it as cancer has been brought into my life for some reason to be my teacher. My question is how can I be a good student and what can I learn from that? So if I get to the other side and I graduate, which I hope to do in early 2024 when the radiation is done and I’m perceived as being virtually cancer free, then I can sort of reflect on that and move forward with my life differently. So a lot of the things I’ve changed in my life, I’m no longer drinking alcohol and I’ve changed my diet a lot and I’m taking all these supplements. I now do hot and cold baths, like plunges, like I do basically ice baths, which is good for you anyways. I do intermittent fasting. So these are things that I can continue to do after this in my new beginning stage, all of which serves my body. I like to think of our body as this rental vehicle we were issued when we were born and over the course of our life, the exterior of this rental vehicle gets more and more dented and a little bit messed up but what’s more important is what’s inside the rental vehicle. Actually, I call it my rental vehicle “Hurts,” because as I get older, it hurts more. But I think that the idea that as we get older, we take care and maintain the exterior of our rental vehicle, what we look like, but, over time, it’s less important what it looks like and it’s more important what it feels like. And some of the things I’m doing are things that are going to help me feel better. They’ll maybe help me look better as well. And that’s what becomes important. When we’re looking at what we’re doing for our body and our health, it’s the question of are we doing it for short-term vanity or for long-term health and vitality? And I’m trying to do it for the latter, as evidenced by just how old I look.

Alex: You don’t look old, you look very young and full of vitality. You always show up, the full you, in my experience of every time we’ve ever talked. So thank you so much for joining me this episode of Coaches on Zoom Drinking Coffee, opening up, sharing your wisdom, super exciting to see all the projects that you have going on, a lot of them crystallizing and evolving early 2024, some potential really cool things that you may be announcing to the world at some point soon. 

Chip: Yeah, I look forward to that. Thanks, Alex. Really appreciate it. Thanks for the great work that you and Charlotte and the team do for the world. 

Alex: Thank you.