The following is a transcript of this episode. It may have been edited for clarity.
Teaser: What would be your next move if you had already disrupted the hospitality industry? Not once, but twice. Burst is the founder and CEO of the world’s second largest boutique hotel chain. And then as the head of Global Hospitality and strategy at Airbnb, for Chip Conley, the decision was clear, he would now disrupt the concept of aging out by opening the very first school dedicated to people in midlife, and helping them navigate this life stage with a renewed sense of purpose and possibility. Besides talking about this amazing school, which you are definitely going to want to enroll in. Chip and I are going to chat about how intergenerational collaboration is becoming essential in the workplace, how our personal operating system shifts as we get older, and ways we can cope with all those transitions we’re facing and midlife chips also going to school us on all the hormonal stuff that men go through during this time. That’s right, ladies, you’re not alone. And we’re going to discuss how we can communicate with one another about the changes we’re experiencing. I am so excited for you to listen to my conversation with Chip who’s filled with so much kindness and wisdom and insight. So stay right where you are.
Intro: Welcome to More Beautiful, the podcast for women rewriting the midlife playbook. I’m Maryann LoRusso, and I invite you to join me and a guest each week as we strive for a life that’s more adventurous, more fulfilling and more beautiful than ever before.
Maryann: Welcome back, my esteemed guest today is on a mission. Chip Conley disrupted the hospitality industry not once, but twice. First as the founder of Joie de Vivre Hospitality, the second largest operator of boutique hotels in the world, and then as the head of global hospitality and strategy for Airbnb. Inspired by his experience with intergenerational mentoring at Airbnb, Chip co-founded the Modern Elder Academy, the first ever midlife wisdom school that’s dedicated to reframing the concept of aging, and helping students navigate midlife with a renewed sense of purpose and possibility. Chip is also the author of many books, including Wisdom at Work: the Making of a Modern Elder and the upcoming Learning to Love Midlife. 12 Reasons Why Life Gets Better With Age, which I can’t wait to read. Chip, it’s a joy to have you on the show. Welcome.
Chip: Hello, Maryann. I’m in the closet with you!
Maryann: [Laughs} Yes, welcome to my closet!
Chip: Oh my gosh, I love it. I love what you’re doing, so it was easy to say yes to this.
Maryann: Thank you. I appreciate that…OK, first question. And we’re going to start with a kind of heavy one, but I promise we’re gonna get lighter after this. I read somewhere that your mission to reframe midlife began during a really hard time for you. You had lost five of your friends—all middle-aged me—to suicide. I’m so sorry. And you were also experiencing your own personal challenges. Can you tell us about the realizations you had during this time? And why you began to scrutinize how our culture conditions us to feel as we approach midlife.
Chip: Yep. So…first of all, let’s talk about the social science research around the U-curve of happiness. So this is research that’s been done globally, across cultures. And what it shows is that pretty consistently, there is a decline in life satisfaction that starts in our early 20s and bottoms out around age 45 to 50. If you want to get technical, age 47.2 Is the low point.
Maryann: Wow.
Chip: And your your mileage may vary, because these are all averages. And of course, this doesn’t describe everybody. But around 45 to 50 people have their low point in life satisfaction as an adult. And then with each passing decade after 50, you get happier and happier. So [the U curve] is like a smile. But the bottom of the smile is 45 to 50. I know that now, but I did not know that during the Great Recession 15 years ago. And I did lose five friends anywhere from age 42 to 52. Three of the five were entrepreneurs whose businesses had just fallen apart during the Great Recession. But I think in all five cases, they were going through some stuff. And they didn’t necessarily feel like they had the resources or a school or a tool to help them understand what they were going through. Some might call this the midlife crisis. But the term midlife crisis…
Maryann: It’s a bad brand.
Chip: Yes, midlife has as a brand and the brand is crisis. Let’s be clear: Yes, it is the word that most is associated with midlife. I was lucky enough, a month or two ago, to give a talk at the big TED conference in Vancouver, around my idea that midlife is not a crisis, it’s a chrysalis…
Maryann: I love that.
Chip…and the idea that we move from this caterpillar stage where we’re consuming and producing in our 20s and 30s and 40s, and then…we create a chrysalis, or the place where we have the space to get soft and gooey, and it’s sort of liminal and full of change and sometimes somewhat solitary. But on the other side of that transformational crucible comes this winged, beautiful creature that is the butterfly. And again, that U-curve of happiness suggests that we do get happier. So I’m a big believer at this point that midlife is the era of transformation in one’s life. And yet, we really need to help people understand that if you’re going through something, it’s normal. And some of it’s like, you’re navigating midlife transitions. You may be going through empty nest, or you might be having your parents pass away, or you may be going through menopause, or you may be getting divorced, you may have a health diagnosis, you may be fired because of ageism. There’s a lot going on around age 50. But that doesn’t necessarily mean that it’s the end of your career or your life. It actually might be the opening of something new. So that’s what I learned through…I had a flatline experience where I died seven, nine times.
Maryann: You did?
Chip: Yeah, I had an allergic reaction to an antibiotic. And that was what woke me up at age 47. Like, OK, this isn’t working. I’m willing to make a lot of changes. Part of the challenge for people is making a lot of changes around age 50, and that’s part of the reason we created the Modern Elder Academy (MEA), to help people through their midlife transitions.
Maryann: Right. People need so much support during this time. I couldn’t agree more. But what I love is that the first time you were called an “elder” was when you were 52. It’s too young, in my opinion. But you know, what do I know? You had just sold Joie de Vivre when you got a call from the young founders of Airbnb, who asked you to help them grow into a global hospitality giant. You were twice the age of the average Airbnb employee. But instead of feeling like the old guy in the room, you formed some memorable relationships that you described as mutual mentorships. Tell us about this intergenerational mentoring and what it inspired in you.
Chip: Yeah. So I was on the other side of 50, and a couple years after it sold Joie de Vivre at the bottom of the Great Recession. I was trying a lot of things out, I was curious, I had some space in my life, which I wasn’t used to. And out of the blue, I get this call from the CEO and co-founder, Brian Chesky, saying, I want you to help us democratize hospitality. It was like, OK, that’s a great opening line. But like, tell me what Airbnb is…This is a long time ago. This is before anybody had heard of Airbnb. But they were growing fast. And so he came over, we spent hours together and I said, yes, I’ll join. But I didn’t really realize that I was joining a tech company. I mean, Chip, knock-knock, like, what was happening in my head, like, of course, Airbnb was a tech company. But at age 52, I’d never worked in a tech company. So I was supposed to come in and be the wise elder. They called me the modern elder because they said I was as curious as I was wise, which I appreciated. You know, that’s a nice alchemy of curiosity and wisdom. But I realized pretty quickly that I was going to learn there as much as I was going to teach. And I had to be curious. And so what happened over the course of the next seven-and-a-half years (four years full time, and then three-and-a-half years as a part time advisor) was that I had over 100 mentees. And when you hear mentor and mentee, you sort of think, OK, well, you were teaching them something. In almost every case, I was learning as much from them as they were from me. And then I coined the term “mentern,” because I was a mentor and intern at the same time. And it makes sense to mentor. It was the idea of like, how do we show up in life, and know that sometimes we have the hat on of being the curious learner. And sometimes we have the hat on of the sage teacher. And ideally, I had some of these relationships where it was almost like a yin and yang. I was learning that thing from them that I needed to learn, and they were learning the thing from me that they needed to learn, and we were both better off for it. So you know, with five generations in the workplace for the first time, and with by the year 2025 the majority of Americans having a younger boss, this is a whole new workplace we have never seen before. So we gotta learn how to learn from each other.
Maryann: That is so beautiful, because there’s so much negativity I feel surrounding like the generations and how we feel about each other—even in jest, right?
Chip: Yeah.
Maryann: And it blows my mind that you you say there are now five generations now working together. And studies show that age-diverse teams are more effective. But you’ve pointed out that not many corporate diversity and equity programs even address ageism. Do you think the modern workplace is going to survive if we can’t figure this out? Do companies need to embrace these cross-generational mentorships?
Chip: It’s starting to happen. And it’s happening for a few reasons. Number one is, people are staying in the workplace longer. So people are holding off on retirement. And so that means you’ve got an older population staying at work. So that’s one thing. Number two is, the unemployment rate has been—other than a spike at the early stages of COVID—really low for a while. And so companies are now starting to think, OK, maybe we need to think about recruiting differently. Maybe we have “returnships,” where someone comes back to work after having retired—maybe they realized two years into it that they don’t love retirement, and they want to come back. Or maybe we need to start looking at, how do we go out and find pools of potential people we would hire who are in their 50s, or their 60s, which is not what we would normally think of when we think of a company’s recruiting function. [It’s typically been] like, which college campus are you going to this week? So I think we’re gonna see, by necessity, more of this. But I think the other piece is there’s just a growing awareness that young brains and old brains, when they work together, can have the best of both worlds. The data is pretty conclusive on this. The younger you are, you’re fast, and you’re focused, you’re like a flashlight. And when you’re older, you’re like a lantern. And the difference is, the flashlight is really good for certain things. The lantern is really good for certain things. Having both gives you the best of both worlds. And so that is what the data is showing: when you have intergenerational teams, the team works better. Not always, and there can be friction. But what we need to learn is, how do we help the different generations work together on a team? So that’s like a generational potluck.
Maryann: So we have to stop with those Boomer jokes and those millennial jokes and all that.
Chip: Yeah, and just remember that there are still Gen Zers and Gen Xers out there too.
Maryann: Yes, Gen X in the house! We’re the forgotten generation.
Chip: Yes, I know.
Maryann: I love that you say we get smarter about our humanity as we age. In your Modern Elder TED talk, you said, “We are shifting our primary operating system from ego to soul. And in the soul’s quest for wholeness, what if aging is not about growing old but about growing whole?” That is so beautiful, Chip. Can you elaborate on this metamorphosis that you believe occurs during midlife and why we become less ego and more soul?
Chip: Well, I’m not the first person to say this. Carl Jung, the famous psychologist, said it. So did Richard Rohr, the well-known Christian mystic, who’s actually a student at MEA…They both have said that there’s a lot of evidence that in the first half of our adult life, it’s really about our ego, and individuation is the structure in our propels us forward. But around age 50, there’s this operating system change. And what used to be the organizing principle, “What’s in it for me?,” shifts to, “How do I serve?” What Eric Erickson said is, “I am what survives me.” And so that happens. And the other thing that’s happening in the brain, which Arthur Brooks wrote about in his book From Strength to Strength, is we move from fluid intelligence to crystallized intelligence. And fluid intelligence is when we’re thinking again, like that flashlight, everything’s very focused. And it’s very linear, typically. And after age 50, the thing that becomes more prominent is that we connect the dots, we’re better at intuition. We’re better at thinking holistically and systemically. And so as a result of that, it means that, yeah, if you’re thinking systemically, you’re thinking like the whole, and whether that’s the whole in how you see yourself, or whether that’s the whole as for me at Airbnb, being the strategic thinker…and strategic thinking is holistic thinking. It’s thinking systemically, it’s actually seeing beyond what the flashlight can see. And so I think that that’s a real opportunity. And I think the idea of growing whole speaks also to alchemy. When we’re young, we’re polarized…You know, I’m an introvert or I’m an extrovert, or maybe I’m a piece of both, but I don’t know how to actually integrate those. One of the things we get better at as we get older as we learn to integrate curiosity and wisdom, gravitas and levity. How do you integrate all of these parts of yourself, so that by the time you’re in your 50s 60s or later, you feel like an integrated whole? So you don’t have feel like you have to show up with one group of people and act one way and then with a different group people act in another way—that’s what you did in your teens and your 20s, and your 30s, and maybe your 40s. And now you’ve moved beyond that. And you and you get to a stage where you’re like, I just show up with whoever I am. And I’ve integrated those parts of myself.
So I think aging is about alchemy. And if you look at some of the some of the things that we love [that age well]: cheese, or wine, or pickles…What’s going on is that there is alchemy. There’s an alchemy, where the tannins in a wine, mellow and the flavors [expand]. So if it’s true for for wine and cheese and pickles, or kimchi or whatever fermented food you like, then it’s true in humans: We get better at alkalizing all of the parts of ourselves. So that by the time we hit our 50s and beyond, we are this integrated, whole human that is, you know, sort of at its best.
Maryann: That’s amazing. We need a T-shirt that says, “Aging is alchemy.”
Chip
I love that. I love that.
Maryann
So your book Wisdom at Work inspired this incredible endeavor, the Modern Elder Academy, which is the world’s very first place dedicated to long life learning, which is—and correct me if I’m wrong—the self-initiated education that’s focused on personal development…
Chip: It’s how to live a life that’s as deep and meaningful as it is long. It’s understanding life stages. Lifelong learning is one thing. Lifelong learning is, at 30 or 50, or 70, I am continuing to learn, and that’s a fine thing. But a subset of lifelong learning is long-life learning, which is how to live a life that’s as deep and meaningful as it is long, and it’s based upon understanding life stages. Lifelong learning could be like, I’m learning about British history, like, Oh, that’s great. But that’s not the same as long-life learning.
Maryann: Got it. So tell us why you thought we middle-agers needed our very own school, and what students experience at MEA and what you want them to walk away with.
Chip: Yeah, we have 3,500 alumni now from 42 countries and 26 regional chapters. Our very first campus is in Baja, on a beach, five acres on the beach, an hour north of Cabo San Lucas in Mexico. Our second campus will open in Santa Fe, New Mexico, in March on a 2,600-acre regenerative horse ranch. I started it with two co-founders because we have no schools or tools to help people in midlife. You know, we’re going through all these transitions, and feel like we’re getting the Game of Life wrong. And it would be great if we actually had a little bit of instruction to say, Oh, here’s an easier way to get through this transition. So with five key pillars of our program: how to cultivate and harvest wisdom, how to reframe our relationship with aging—because actually, as Becca Levy from Yale has shown, when you shift your perspective and start aging from a negative to a positive, you gain seven-and-a-half years of additional life—how to move from a fixed to a growth mindset, navigating the life transitions and empowering a regenerative lifestyle and purpose. Those are the five pillars. And we also have online programs, so you don’t have to come to Baja or soon to Santa Fe. But what people get from a five- or seven-day workshop is a deep dive into life changing conversations that help you to understand how to live the second half of your adult life. The average age of the people who come to MEA is 54. The average age they think they’re gonna live until is 90. Let’s do the math for a second…
Maryann: Interesting.
Chip: From 18 to 54 is 36 years. From 54 to 90 is 36 years. Most of us at 54 do not think that we’re halfway through our adult life. But if you actually do think that way, you start to ask questions like 10 years from now, what will I regret if I don’t learn it? Or do it now? And those are the kinds of questions we help people with. We help people to ask questions that help them to consciously curate their life. And with the respect and the understanding that they may have more life ahead of them than they had planned.
Maryann: Wow, so amazing. I’m so glad you did this.
Chip: When are you coming down?
Maryann: I am going to come down…I’m going to come down first as a journalist and guest, and then as I’m going to do…I’m gonna be a speaker one day…
Chip: You’re gonna be a teacher. Yeah, I love that. Love that.
Maryann: But what I really want to talk to you about is something that’s a little more personal…Because even if we feel that this is a transformative time, the physical changes that occur during midlife can be so challenging. This statement on your website really resonated with me: “Some of our transitions are personal and voluntary, others are external and involuntary. Midlife is filled with more transitions than any other time of life.” Now most women I know would agree with that, because menopause can really give us a kick in the butt.
Chip: Right.
Maryann: And you’ve written about andropause, or male menopause, which hasn’t been talked about much.
Chip: Yeah.
Maryann: What would you like women to know about the physical changes men are undergoing in midlife? And on the flip side, do you have any tips for women on how to communicate to the men in their life all the changes they’re experiencing?
Chip: Oh, my gosh. I have a daily blog called Wisdom Well. And I wrote a Wisdom Well post not long ago about my “manopause,” because I have prostate cancer and I’m on hormone depletion therapy. And when you have hormone depletion therapy, it means you go through accelerated manopause. So I experienced andropause in my 50s, and now in my 62 and experiencing hot flashes, night sweats, brain fog, certain fatigue, challenges with sleep, etc. So I literally wrote a blog post about this—maybe you put it in the show notes or something like that.
Maryann: I’ll link it.
Chip: Because quite frankly, I said like, these are the things that men need to know about the women in their life. Because it’s not easy….Let’s start by saying that menopause is something that’s not talked about enough in society and amongst women. I think it’s really finding its era right now where people are talking about it more, but there needs to be a rite of passage. This is like a really serious thing that is going on in a female’s body and a woman’s body that deserves conversation and reflection on like, what is ending and what’s beginning. So whenever there’s a transition, there are usually three stages. There’s the ending of something, the messy, middle, and the beginning of something new. That’s the frame, and the hero’s journey. Joseph Campbell’s work speaks to this as well. So the ending of something, when it comes to menopause, would be perimenopause and the early stages. And then there’s the messy middle…where no one gives you instructions that tells you [how long it will last]..It’s different for everybody.
Maryann: The uncertainty is what kills you.
Chip: That’s right. And that’s messy. Middle is very much about uncertainty. And then the beginning of something new is like, oh, my gosh, I am on the other side of this. And so if we as a society, or if someone in menopause could come to me and understand how do I understand the frame of these three eras of the transition that would help. And then if men can be more understanding of just what women are going through, andropause is something serious, but it is not. It’s not a rite of passage that like menopause is. So what’s happening and Anthropos generally speaking, some of the things you start to get a gut, you know, that is one of the number one things that men notice, when they’re going through enterprises like there is a there’s a reaction that your gut, your gut starts to get bigger, their libido starts to go down, they start to sometimes lose some hair, it’s actually a time when especially on their legss…And it may start losing some energy. And so andropause is the reason I say it’s not a rite of passage, though, is because it’s not the end of an era. You know, for women, it’s the end of an era, it’s the end of the childbearing era. For a man, it’s not the end of their child creating era. And therefore it’s for that as well as all kinds of other reasons. Because the the symptoms of menopause are not nearly as serious as men and menopause. I wouldn’t, I would, I’d say men, men got it easy. And men don’t even know like most of them don’t even know what anthropods is, let’s be honest. Yeah. So they’re just going through this thing. And but actually, the fact they don’t is actually unfortunate, because for women, at least there’s something that they can pinpoint. And they can talk to their girlfriends about it. But for men, they’re going through some stuff and it’s actually generally not good stuff. But they just feel like they’re like a slump. They’re like, like they’re not working out enough because they’re, you know, or, man, I’m just, you know, I’m getting old and, and frankly, a lot of men go into this downward spiral where they just stopped taking care of themselves. And andropause is the early stage of that for some of these men, and they just feel like you know, just, you know, to heck with it. I’m not going to even try to do this.
Maryann
Do you think if they knew what was going on biologically that they would be more prone to kind of turning it around for themselves?
Chip
I think so i think so because I think it. So what happens so often as we personalize it, we feel like there’s, we’re doing something wrong. And in feeling that you end up losing your sense of confidence and, and some, some men might like, power on but a lot of men just sort of give up.
Maryann
What would your message be to men out there who are listening about how to handle that?
Chip
Number one, do a little bit of research on what andropause is and what are the indicators that you may be going through it? Number two is Yeah, and maybe a time where you need to be, you might start moving out of what you’ve historically done for athletics. For example, I was a runner, and then my, you know, my knees, my ankles, like, okay, so I but I’m now like crazy about how much I walk, and how much I swim. And so you know, you need to up the ante on some of the thing back in the day you can take for granted. Yeah, I didn’t work out this week, and I still look great. But like, that doesn’t happen. That does not happen in your 50s. No. And so you better actually start to look at a new forms of exercise that are going to be helpful.
Maryann
Yeah. And I think it’s so important for us to talk to each other about it. You know, and women are you right? Like it’s becoming less of a taboo. I think menopause is having a moment, there are so many women out there talking about it. And maybe that’ll trickle down to the guys. Right. And maybe we’ll all start talking about this with one another.
Chip
Hopefully, maybe, but the fact that men I mean, women know what menopause is, men don’t even know what Andrew poses. So there’s, there’s like an education piece to it first.
Maryann
Are you addressing that at MEA?
Chip
Yeah, we do. We do.
Maryann
That’s so great. So…I have one more question for you: You said in 2018 that experience still matters because Google doesn’t yet understand nuance, like the human heart and mind. I would like to know what your take on that is now, five years later, with the emergence of chat GBT and all this other sophisticated AI. Are you scared yet, Chip?
Chip: You know, I in terms of the robots and chatbots taking over the world, I’m not going to even address that. I haven’t spent enough time thinking about it. I have listened to a few podcasts on it. But I’m not. And I’m mixed. But when it comes to the idea that wisdom or experience make it my might go away because of the value that might go up because of AI. I’m not worried at all. Because AI doesn’t ai ai as Picasso said long ago, computers are useless. They only give you answers. Chat GBT gives you answers, it doesn’t give you questions. It doesn’t ask the nuanced catalytic question that might open up a new idea in your in your world. Chat, GBT doesn’t have intuition. It doesn’t actually understand ingenuity or creativity. It can actually, overtime, maybe it gets better and better. But it does. It does not have the ability to metabolize experience, which leads to distilled compassion. That is my definition of wisdom. So it is a great organizing principle for the knowledge of the world. And I think what this is really helping us to see is that there’s a difference between knowledge and wisdom. Knowledge is something you accumulate, and chat GBT actually make sense of that knowledge. Wisdom is something you distill, based on life experience. And based upon that you have life lessons, that, you know, can actually be valuable, not just to you, because MBA, we say wisdom is not taught it’s shared. And how you share that wisdom with others allows them to have a better life as well.
Maryann
From your lips to God’s ears.
Chip
Yeah.
Maryann
Thank you, Chip, for all you’re doing. And for Modern Elder Academy and for your books. I can’t wait to read the new book. It’s coming out in January, right?
Chip: That’s right.
Maryann: Can you tell our listeners where they can find you online and learn more about MEA?
Chip: Yes. Modernelderacademy.com is the website for the Academy. Chipconley.com is my website My daily blog can be found at the MEA website, or you can just Google it. And I also put it up on my LinkedIn profile Monday through Friday, so you can also just follow me on LinkedIn.
Maryann
Great, we’ll put all those links in the show notes. Chip, thank you so much.
Chip
Thank you.
Outro: Thank you so much for tuning in to More Beautiful. Please visit Morebeautifulproject.com for show notes and bonus content. And it would mean so much if you could subscribe, rate and review on Apple Podcasts or wherever you’re listening. Together, let’s continue to change the conversation around aging.
