Can changing your mindset increase your lifespan?
To kick off season two of How We Future, Lisa sits down with Chip Conley, entrepreneur, bestselling author, and founder of Modern Elder Academy. Chip has spent decades helping people rethink aging, midlife, and what it really means to live life to the fullest.
In their conversation, Chip and Lisa explore the idea of the “midlife chrysalis” and why the years around 45 to 55 can be a powerful period of transformation rather than decline. Drawing from his own near-death experience, his work in hospitality, and his time at Airbnb, Chip offers a hopeful and grounded reframing of aging.
You’ll hear about:
How wisdom is distilled from experience and why it matters now more than ever
How curiosity and energy can counter ageism at work
What hospitality, community, and belonging have to teach us about the future
From emotional equations to regenerative communities, this episode is a reflection on learning, leadership, and designing a life with intention. If you are navigating change or wondering how to grow older with more joy and agency, Chip offers language, frameworks, and perspective to help you maximize your life.
Links from the episode:
Chip’s podcast, The Midlife Chrysalis
Learning to Love Midlife: 12 Reasons why Life gets better with Age by Chip Conley
Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life by Chip Conley
10 Commandments or Commitments, by Chip Conley
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Lisa Kay Solomon: I’m Lisa Kay Solomon, and this is How We Future, where I talk to some of my favorite changemakers about shaping tomorrow, starting today. I can’t think of a better way to kick off this season of How We Future and my next run around the sun than with my dear friend Chip Conley. Chip has been a huge inspiration to me for years. He has an amazing talent to reframe the way we think about aging, wisdom, and possibility.
From building Joie de Vivre into a hospitality empire in his 20s to founding Modern Elder Academy in his 50s, Chip has spent his career pioneering new answers to the question, what does it mean to future well? In our conversation, we talk about midlife as a chrysalis, not a crisis, why wisdom is becoming more valuable in a world driven by speed and AI, and how joy and energy can be powerful leadership tools at any age.
This episode is full of advice to take into the new year. Let’s get started with Season 2 of How We Future.
I cannot think of a better person to kick off Season 2 of How We Future and this new year than with my friend Chip Conley, who has been a huge inspiration to me for so many years and really embodies everything that this podcast is about, around helping people find more generative and joyful ways to shape their future. Chip, thank you so much for being here with us today.
Chip Conley: Those are two of my favorite words, generative and joyful. I started a boutique hotel company based on the French term Joie de Vivre. Generative is part of what I do today. We even call it our residential communities at MEA, regenerative communities. You and I are on the same page.
Lisa: Well, I love it. You’re an entrepreneur. You’re an innovator. You’re a thought leader. Seven bestselling books. New podcast. We’re going to talk about a lot of them. The things we don’t talk about, we’re going to put in the show notes. Chip, I don’t know if anyone has ever called you a public philosopher. Preparing for this, I realized you’re so much more than all of those things.
You’re both one of the best futurists I know because when you put something on the map, you don’t just put the thing on the map; you reframe how we think about it, and that, to me, is a futurist move. Because you’re so good at naming things and then changing our frames, you literally change our relationship with those things.
Chip: That’s interesting. No one has ever called me a public philosopher. People have called me a philosopher before. I don’t know what the difference between a private philosopher and a public philosopher is. I like public philosopher because it suggests there’s an intent to not just use your philosophy to be one-on-one with people, but to actually influence, maybe societal norms and the lexicon we use.
Thank you. It’s interesting. When it comes to futurists, I was just talking to someone this morning, a young person who wants to be a futurist when they grow up. He’s 25 years old. I said, “Isn’t it interesting that all of the best-known or most of the best-known futurists in the world are 50 and up, and most of them are even older?” Futurism is a form of crystallized intelligence, being able to synthesize and connect the dots, which is something we get better at as we get older.
Lisa: We do. It’s really been my life’s mission since we met decades ago, when I was at Global Business Network, and you were one of our remarkable people. We were trying to use practices of futures to help leaders imagine a multiplicity of futures. For me, the last 15 years has been trying to shrink that gap between the futurists that are up there and thinking and all of us, our ability to think imaginatively about the kind of worlds we want to be in, and also to learn the skills of anticipation and, as you were saying, of sensemaking, about taking in a wider swath of perspective and trying to understand what they mean in order to pose a new question of what could be.
From that way, I feel like, again, you have done that again and again, right? Not just asking why, but why not? I wanted to start with your most recent chapter in the spirit of reframing around reframing midlife. In preparing for this, I realized I should really start with huge gratitude, Chip, not only for all that I’ve learned from you over the years, but in re-picking up your book, Learning to Love Midlife, and going deep on Modern Elder Academy and what you’re offering, and we’ll talk about it, I realized that this podcast, How We Future, is my midlife chrysalis.
Chip: [laughs] I love that. I love the term. Let’s explain the term for a moment. I’ll make it personal. I started a boutique hotel company when I was 26, ran it till I was 50, but in my late 40s really struggled, and friends of mine were saying, “You’re going through your midlife crisis.” I was like, “Ah, I don’t believe in midlife crisis,” but I knew I felt really awful. My life was falling apart in a variety of ways.
Then I had an NDE. I died and went to the other side 9 times over 90 minutes due to an allergic reaction to an antibiotic. It woke me up. It woke me up to trying to understand this stage of life that is the Rodney Dangerfield of life stages, which is it don’t get no respect, this midlife life stage. I came to see my 50s. I loved them. I was like, “Wow, what is this about? Why would I not like my late 40s, and I love my 50s?”
Then I found out about something called the U-curve of happiness, which in fact shows exactly that, that the low point in life satisfaction as an adult is typically around 45 to 50, and then we get happier with every single decade after that until we die. For me, that helped me to see maybe there’s a purpose for midlife, especially 45 to 50. Maybe the purpose of that stage of midlife is to liquify as a caterpillar does in a chrysalis before you can reform yourself as the butterfly.
That’s how the midlife chrysalis term came about. That’s the name of my podcast as well. I think it’s really apt because I’ve seen now we’ve had over 8,000 people go through our programs at either our Santa Fe, New Mexico campus or our Baja campus on the beach in Mexico. 8,000 people is a lot of people over the course of 8 years. I see over and over again that there’s a rough stage around midlife that’s early-ish midlife in a world in which more of us are living till 90 and 100.
How do you help people to get through that period of time to realize that on the other side of that rough patch, coming through the chrysalis, is the butterfly? That’s how I’ve experienced it the last 15 years. I’m 65 now.
Lisa: It’s incredible. It just gave me a language to talk about what felt like regenerative growth, this kind of unleashing of not only creativity, but of all of the strengths and assets that I had built up over the years. I love the way you talk about it as holistic wisdom. It’s like this thing that connected all the things I’ve done and allowing to bring it to the world in a totally new way. I’ve literally had people say to me who have not even listened to the podcast, “Lisa, you just seem so much lighter. You’re radiating.” I was like, “I know. It’s incredible.”
Chip: You’ve let go of all the Fs, I would say the F-U-C-Ks. That’s one of the 12 reasons why life gets better with age. The subtitle of my book, Learning to Love Midlife, is 12 Reasons Why Life Gets Better with Age. That’s really the main point of the book. Becca Levy at Yale has shown that when we can shift our mindset on aging from a negative to a positive, we gain 7.5 years of additional longevity, which is a shocking stat, but it’s been in place for 20 years now, that statistic.
How do we help people to see the upside of getting older? What’s the unexpected pleasure of aging? There are 12 of them that I was able to research with academics. 1 of the 12 is that sense of freedom that comes from saying, “I have no more fucks left to give.” Excuse my French. For women, it’s particularly resonant because, for a lot of women, they grew up trying to live up to some standard and people-please and do a lot of things to satisfy the patriarchy or the world in which they had to fight for growing in their career, for example.
To get to a place where it doesn’t mean when you have no more F’s left to give that you don’t care about things, it’s just you’re more discerning what you do care about, and you don’t sweat the small stuff, and you start to learn how to edit your life in a way that focuses on what will let you flourish. That’s part of the reason you feel better after age 50, Lisa.
Lisa: I’m so grateful and focused in a way that perhaps I didn’t have the judgment to have or the connection between my internal values and the choices that I make. I know you talk a little bit about that in a healthy way. Maybe it is because it’s like, “Oh, wait, we don’t have infinite time on this earth, right? I feel that my time is getting-- not that it’s running out, but I just want to be, as you said, a bit more discerning with that.” That’s an evolutionary trait that we can utilize to our advantage, versus feeling fearful about it.
Chip: Yes. I think Laura Carstensen at Stanford has a theory called the socio-emotional selectivity theory. What it shows is that the shorter amount of time you think you have left in your life, due to cancer, AIDS back in the day, due to being older, the less time you think you have, the less you focus on the future or the past, and the more you focus on the present moment.
In focusing on the present moment, we learn how to actually be happier. Actually, there’s something to be said for death. Death is a remarkable organizing principle for life, which is why the Never Die movement with Bryan Johnson and all of his minions is sort of a silly movement, because knowing that you have a finite time on this earth gives you a sense, like a catalyst, of how you’re going to use that time and what matters. The what matters piece is what you’re talking about, is you get really clear about “How do you focus on what matters, and who matters?”
Lisa: Oh, it’s so empowering in that way. I know throughout the book, you also talk about your 10 Commandments, these commitments that you have made by having a better understanding of how to reframe midlife. One of them, you talk about focusing on the eulogy values versus resume values, which I think is such a big one.
Chip: That’s my favorite of the 10. Let me just give a framing for this. I grew up with 10 Commandments, and 8 of the 10 are about thou shalt not. I always felt like they’re a little bit harsh, and they don’t change. I was like, “These are the 10 Commandments, and they’ve been in place for 2,000 years.” I have created 10 Commitments, and mine can evolve, and they do evolve. What I mean by 10 Commitments is these are the ways in which I commit my life.
One of them, the one that you just mentioned, is to learn how to live your life based upon your eulogy as opposed to your resume or your LinkedIn profile. I got to say that the first half of my life, I lived my life based upon my resume, my LinkedIn profile, and my ego. From that point, when I had my NDE, near-death experience, I really started to see, like, “Wow, I’m seeing an operating system shift in my life from my ego to my soul.”
In that shift, I got much more curious about my impact in the world, not my return on investment, but my ripples of impact, a different form of ROI, and it really helped. It helped me to recognize that the impact we have on others, it’s not about the legacy of having my name on a university building; it’s more about knowing that you’ve had an influence. This is why I love the movie It’s a Wonderful Life, which is just such a testament to one person’s impact on others when Clarence the Angel comes down to the bridge where Jimmy Stewart is and shows Jimmy Stewart what his Bedford Falls town would be like if he had never existed.
It’s that kind of, I wish we had technology. There’s lots of technologists in the world. I wish some technologists could come up with a means of helping us see the impact we’ve had on others because that’s what really makes life worthwhile.
Lisa: I love that framing. I try to live by that, actually, most days. Even when I welcome my students to a class, or when I pick something up and I just take a moment, and I say, “Thank you. “ In fact, just this morning, I had a super early medical appointment, like 7:00, 10:00, obnoxious early. Just to make it even trickier, they said no caffeine. I was like, “What? Okay, fine.”
The very first thing I did when I got there was I just looked at the technician, and I said, “Thank you so much. Thank you so much for being here. Thank you so much for enabling me to get this important test.” She looked at me, and she goes, “I really appreciate you saying that. Nobody pauses to say that.” I love how you’re describing impact, both at the larger level in terms of how we live our life, but also in the many moments that we can make.
I really love, Chip, that your roots are deep in hospitality. That has always been a pull for me. I don’t know if you know this. My grandfather was in the restaurant business, and so I grew up obsessed with hospitality. I went to Cornell and was always longingly I was a hotelier. I took as many classes there as possible, and I think it’s because you could get that feedback loop quicker of, “You make this choice, and as a result of this choice, this happens.” Now, I would call that design more broadly. I just love the immediacy and intimacy of those moments.
Chip: When I was a kid, they did ask me, I had to draw a picture of myself at maybe age 8, and then say, what careers do I want to be in? One of the careers I said, along with being a sports reporter on TV and a movie star, was being a hotel man. That’s what I called it, a hotel man.
Lisa: I’m seeing the cape now. It’s hotel man.
Chip: Hotel man. I will say that as I got into my adolescence and then high school and college, hotels were not my thing. I was very interested in commercial real estate, and hotels are commercial real estate, so there was a connection there. It wasn’t until I graduated from Stanford Business School at the very ripe old age of 23, I was very young, and I went to work for a real estate developer in San Francisco, and San Francisco was full of hotels.
I was like, “Wow, hotels are a form of real estate. They’re a lot more creative, more interesting.” What I realized was, serving people gives me joy. I thankfully started to study hotels at about age 25 and realized that there’s a whole new movement called the boutique hotel movement. The future of hotels was boutique hotels. I then decided to create a boutique hotel company, call it Joie de Vivre, and over the course of the next 2 dozen years, created 52 boutique hotels around California.
I loved it. I loved the fact that it’s a noble profession because if you do your job well, you make people happy, and you keep people safe. There’s something about that that feels just deeply rewarding for me. I’m also a bit of a social alchemist, which means I’m a mixologist of people. I think being a hotelier and a restaurateur and a bar-owner and a spa-owner, these are industries that often you’re mixing people together, less so in a spa, but to some degree you do.
Finding something that was very natural for me, thank God, I found it. Today, even though I’m no longer running boutique hotels, I am at a stage in my life where I’m very clearly using those skills and the social alchemy skills at the Modern Elder Academy, which we’ll talk about.
Lisa: Yes, definitely. It’s worth saying, and we’ll put a link to this, of course, that the 52 hotels, they were not the same cookie-cutter hotel. Each one had its own creative expression and personality.
Chip: Own name, own identity, yes. No one of them was the same. We were like a branding agency too because we were good at both design and creation and construction and usually renovation of hotels into-- We would take Best Westerns and Holiday Inns and Sheridans and turn them into boutique hotels, and then we would create these really unique services and amenities there as well.
The fact that each hotel had its own personality, its own language on its Do Not Disturb sign on the back of the door that you’d put on the front of the door, each one had its own flavor, that’s what made it different. Yes, I loved it until I hated it. In my late 40s, I hated it. It was partly because of the Great Recession, but it was partly because I had found a new passion, which was writing and speaking, and I really wanted to do more of that. During the Great Recession, I felt handcuffed to my desk and running out of cash.
Lisa: Again, such a courageous choice to say, “Look, I’ve built this thing, and it’s no longer working for me. Let me try something else.” Your book, Peak, which really talked about what creates great cultures and what really helps people do their best, is just a classic, and I think should be taught for anyone that is in the business of service, so yet another gift that you’ve given so many of us.
Maybe we’ll jump a little bit to Modern Elder Academy and talk about that because it is another form of hospitality. The thing I would say, going back to those unique experiences and now the unique experiences that you’re offering for more than 8,000, congratulations, is that once you’ve had an experience like that, that Peak experience, you’re a different person. You don’t go back.
I think that is so powerful. My very first job working in innovation, I’ll never forget this, was in the early ‘90s. It was a picture is worth a thousand words, but an experience is worth a thousand pictures. That’s what we did. We did experience design because the sort of pack for the punch when you really design something magical, and by the way, incidentally, gosh, you’re revealing so much about me. When I was eight, people said, “What did you want to be?” I said I wanted to be president of Walt Disney World because--
Chip: I wanted to be at Walt Disney. That’s so interesting.
Lisa: It was magic, right? That was my first real immersive experience. I think when you experience magic, and you know what it can be to feel like when you’re in that, that’s the gift you’re giving those 8,000 people and all of the people that stayed at Joie de Vivre. You want to stay there. You come out changed. You come out with a different sense of wanting to recreate that and feel who you were when you were in that environment.
Chip: Really, there’s an in-between stage here that led me to MEA, to Modern Elder Academy. After I sold Joie de Vivre, I had two years of just having space in my life to be curious about what I was interested in. That was interesting. We could come back to that if you want. I learned a lot about a few different things. I was asked 13 years ago at age 52 by the founders of Airbnb to come in and be their modern elder, someone who was as curious as they are wise.
That’s what they said. I joined them and spent seven and a half years there. That was really the future of hospitality. The first thing that Brian Chesky, the founder and CEO, said to me when he was trying to pitch me on the idea of coming in full-time was, he said, “Chip, how would you like to democratize hospitality?” When he first told me about the business idea, I was like, “Oh, that’s a terrible idea.” I was like, “No one’s going to do that.” Of course, I was sort of in this very linear hotelier mind, and then I joined.
Well, I didn’t join. I did some research and spent a lot of time with Brian, and then decided to join when most people had never heard of Airbnb at that time. What I’m proud of is to be able to see the future; that idea is William Gibson: the future is here now, it’s just not evenly distributed. For me, that helped me to see in my 50s how to be relevant and how to find a pro-aging perspective, not an anti-aging perspective, in terms of how to actually make the most of our years after age 50 so that, ultimately, toward the end of my time at Airbnb, I decided to start the Modern Elder Academy.
The reason I did that was because there’s no such thing as a midlife wisdom school. The difference between knowledge and wisdom is the following. Knowledge is something you accumulate. It’s like a plus sign, but wisdom is something you distill. It’s like a division sign. It’s like the square root of something. It’s the essence of something at its core, and the more complicated the world we live in, the more wisdom is important.
In a world in which knowledge is now a commodity due to AI, wisdom maybe has a scarcity value. I wanted to create a school that helped people, mostly 45 to 65, but we’ve had people as young as 25 and as old as 92 come to learn how to distill their wisdom. I define wisdom as metabolized experience, mindfully shared for the common good. MEA launched initially down in Mexico because I had a home on the beach.
I was like, “Oh, I like it down here. Let me start a campus here.” Sort of crazy. During COVID, when, of course, everything had to close, I said, “Well, we have to have a campus in the US.” We bought a former billionaire’s ranch estate, 2,600 acres, a regenerative horse ranch, and turned it into our second campus, which is quite expansive. That’s how MEA got started.
The reason people come to MEA is often because they’re in the midst of some kind of transition, career change, retirement, empty nest, a cancer diagnosis, divorce, moving locations, parents passing away. We specialize in something called TQ, transitional intelligence. Speaking of futurism for a minute, we live in a world in which the pace of change is happening faster and faster, yet very few of us have ever gone through any kind of school to help you understand the three stages of the transition: the ending, the messy middle, and the beginning.
That’s the number one reason people come. The number one reason people come back and why we have 56 regional chapters around the world is because of the fact that people have a deep sense of community. When you get to know people from the inside out, and you all are going through some kind of transition, your cohort stays together and has Zoom calls every month.
You also have regional chapters where you get to know other people who have a common ethos, a common point of view. What I believe, last thought on this, is the idea that mid-lifers are supposed to be like when you’re a teenager or in college, you’re supposed to refuel your car up, and then by the time you get into your 50s, you’re driving on fumes. We need a midlife pit stop that helps people to reimagine and re-engage with how they want to live their life and how they want to curate it.
Because if you’re 54 and you’re going to live until 90, 54 is exactly halfway between 18 and 90, which most people don’t think about. It’s like, “Oh, wow, I have as much adulthood ahead of me as I have behind me.”
Lisa: Again, I’ll just point back to the public philosopher sharing this for the public good. We are all going to hit our 50s if we’re lucky. That is actually not uncertain. In all the uncertainty around us, the fact that we’re going to get older and we’re going to go through life stages isn’t actually not uncertain. That is a given. Your recognition that there isn’t support for this critical life moment, where there could be, and it could be joyful, and it could be regenerative, and it could also build relationships, which are harder to do as you get older as well, in a hugely meaningful moment when you need a boost, it is so powerful to me.
Again, when you see it, you can’t unsee it. When you question, “Why do we think that all of our training around transitions only happens during the adolescence part of our life when we’re filled with counselors and teachers and support, but we have nothing later when we’re feeling more alone, more isolated, more woulda, shoulda, coulda, what do we do with all that?”
You’re giving this beautiful place for people to come and work through it and grow as a human, grow their connections, their friendships, and then be able to give back. I just can’t say enough about it. You didn’t know this, but I’m like one of your greatest unpaid advertisers and promoters.
Chip: Well, we’re going to give you one of our campuses, Lisa.
Chip: Oh, that’s happening.
Lisa: In the Peak model, the book you mentioned earlier, Peak: How Great Companies Get Their Mojo from Maslow, there’s these three pyramids. One is the employee pyramid and their hierarchy of needs. The second is the customer pyramid. The third is the investor pyramid. When it comes to the customer pyramid, the transformational nature of a customer experience is not having your expectations met. That’s the base of the pyramid. Nor your desires met. That’s the middle of the pyramid.
What’s at the top of the pyramid is having your unrecognized needs met. When a company or a service provider provides you something that is beyond expectations and desires, but is a mind reader to understand what you really needed, boy, are you loyal to a company or a service provider like that. What we’re providing with MEA is something that a lot of people don’t know they need.
They just know that they have a disquiet. I sometimes say it’s successful people quietly falling apart in midlife. What we provide is something that people needed. One of the number one things they say on their Guest Satisfactions or Student Satisfaction Forms afterwards is, “I didn’t know how much I needed that.” That’s what I love reading because when you find a service or a product you’re providing that is not obvious, there’s a lot of risk in it.
We’re pioneers. I was a pioneer as a boutique hotelier, I was a pioneer with Airbnb, and I’m pioneers with MEA. Sometimes being a pioneer, you’re like you stand up on your surfboard before the wave has arrived. I started something called Costanoa. It was seven years before the word “glamping” ever existed. It was before the wave was there. It did okay, but it did not do that well.
We had to sell it for a fraction of what we built it for. It was a failure in many ways, but it was a noble experiment, too, because I learned a lot from it. It was an example of when you want to time standing up for the wave, which I was doing this morning. I was literally here in Baja surfing this morning. You want to be able to time your standing up on the board with when the wave is there.
That’s why they’re so valuable, because if a futurist can tell you this is on the horizon and then give you a sense of “What’s the foreshadowing influences that are going to make it more likely to happen, such that you can stand up on the board at the right time?” A futurist can be the difference between you succeeding and failing.
Lisa: I completely agree. As you’re describing that, it reminded me. I teach a class at Stanford called View from the Future, where every week we bring in a guest who’s on the edge of their field to share some of those signals that you’re talking about and let the students not only percolate on what’s happening across different industries, but how they can learn to spot the signals.
Our first guest last year was Mike Maples Jr. from Floodgate, a very famous investor, and he talks about people that live in the future, the folks that are willing to see a trend but also put themselves there or build relationships with people there. The fact, for example, that you went to work with Brian Chesky at a moment where it was like, “What, I’m going to pay money to stay on a stranger’s couch? No, it’s a hard pass.”
You, because, Chip, of who you are, are so curious. You’re so willing to be like, “Wait, what is happening here?” It’s at the beginning of the sharing economy. We were just learning about how to think about new markets related to oversupply in areas that might be able to be monetized, thanks to this thing called the interweb technology. You were not a technologist, but you were an expert in hospitality. The fact that you, A, even took the call and then kept coming in, and like, “Sure, I’ll get a job” when you probably hadn’t had a job.
Chip: I had not reported to anybody since I was 26 years old. I was 52. I was not only having a job and being full-time in an industry, tech, that I didn’t understand, but also, I was mentoring my boss because Brian was the CEO, and I reported to Brian as the head of Global Hospitality and Strategy, while also mentoring him as a leader. Boy, did it take some humility and some patience. Frankly, Brian was a great student. I learned as much from him as he did from me.
Lisa: I’ve heard that. I know a couple of people that worked at Airbnb early on, and just said one of the most energetic learners ever. I think the other part that I’m trying to make, as I try to do my part of democratizing access to futures thinking, because I don’t think the future should be left to just a few futurists, I think we all need to learn these skills, but this idea of really futures as a form of learning.
My mother was a chief learning officer. I grew up really early on getting books of Margaret Wheatley. I’m 12, and Peter Senge. She was a big Deming person, so she talked about quality management and reducing variance. I was like, “Can I just talk about what happened today in the lunchroom?” That’s my weird upbringing.
Chip: Not surprised you’re an academic and a writer. You’re a thinker. Guess what? The acorn didn’t fall far from the tree.
Lisa: That’s right. That’s right. In this time of voracious change, the person that learns the fastest has the best chance of riding the wave, going back to your surfboard analogy, because we have to prioritize the learning over the certainty. Bob Johansen has this great quote. He used to be the president of the Institute for the Future, where he says the future will reward clarity, but will punish certainty.
What I see in what you’re doing is the clarity of your values, the clarity of purpose, the clarity of intent, and being open, like, “Not all of it succeeds,” but what do you do with that? How do you channel that for your next go?
Chip: Yes. I like living laboratories. I love to both learn while leading, and then I like to write about it. That’s very unusual. Sometimes, if you’re a CEO and they write a book, it’s their story, and it’s an inspiring story, but it’s their story. What’s weird about me is that I like leading and I like learning, and I like to create frameworks, like the Peak framework, and then I like teaching.
All of that together, it means being at MEA has been very helpful. The other thing that we’re doing at MEA that’s really interesting is this idea of regenerative communities. Yoga and meditation have become very mainstream, but 40, 50 years ago, they were not. 40 to 50 years ago, intentional communities were like yoga and meditation, but they didn’t really go to the mainstream.
You have communes, you have kibbutzes in Israel. Co-living has become a thing, but it hadn’t really taken off. Because we have this community of people who want to live together and be together, we built a regenerative community around a regenerative farm here in Baja, 26 homes, but now we’re doing these Golden Girls homes. This is Chip at his weirdest again.
It was like, we have all these four, five, and six-bedroom homes, and we have smaller and smaller families. The population is aging. We have a housing stock that is not being used, and 74% of the people single in the US, 65 and older, are women, and 65% of the single people over the age of 50 are women. You have a lot of women who are living alone or would like to live with other women.
In fact, talked about it in college and talked about it in their 40s. Now that’s what we’re doing. I’m literally buying, in Santa Fe, right next to our campus, homes that are obsolescent, four, five, and six-bedroom homes. With our MEA community, which is 69% women, we’re creating a new form of housing that’s scalable. Often, there’s a Golden Girls home, it’s like, “Oh, we’ll live together when we get older, and it’s just a one-off.”
We’re doing it with a community where you have a distributed community, like a village, where there’s 6 or 8 or 12 homes all near each other, right near the campus, so you get all the benefits of the campus while at the same time getting the benefits of being part of the community and choosing your home based upon, “Do you want to be pet-friendly? Do you want to be intergenerational? Is this a writer’s home where writers want to live together?” It’s really interesting.
Lisa: Again, I’ll just call back the futurist orientation of taking a look about where people are and sort of stating the Wayne Gretzky, where is the puck going, right? People want to be together, right? The research suggests that when we are in relationships, it is a resilient and life-giving thing that we can all do, right? How do we create spaces and places that nourish that in a way that’s filled with joy?
Oh, I love it. Is it too early to buy a share? I’m in. I’m down. I do want to say thank you so much for sharing some of your experiences working with Brian Chesky. We are going to put in the show notes one of the best interviews I have heard about your experience that you had with Lenny Rachitsky. That was so beautiful talking about all the really detailed things that you learned around managing someone that had tremendous energy, the founder energy, how to show up for a meeting. I’m actually going to make my students listen to it, so full stop. I just thought that was so extraordinary, that whole conversation and exchange.
Chip: Lenny is amazing. I love that guy.
Lisa: Incredible what he’s built. Just tremendous. I’ve learned so much from the conversations that he has and the way that he does it. The one thing I just want to really maybe spend a minute on from that conversation that I got was the exchange you had around energy and this notion that there is some ageism that still exists within corporations, and we can get very focused on how people see us based on that.
You had this just incredible way of talking about not only the wisdom and the experience that you can bring, but your energy and what that was like. For someone that has been labeled energetic my whole life and not always in the best way, that really spoke to me. I just wonder if you could share a little bit about that.
Chip: Yes. When I was writing my book, Wisdom at Work: The Making of a Modern Elder, about my Airbnb experience, one of the people who read an early version of it was an executive recruiter. She said, “Chip, this book is going to really help a lot of people, especially in their 50s. Because what you’re helping to show here is that ageism does exist, but the question is, what do you do about it personally? We can do some societal things about it, but let’s skip to the personal side because that’s what’s within your control.”
She said, “If you can tell people that if they can show up with curiosity and a passionate engagement for life, for whatever they’re doing, and especially if it’s a job interview, for what the company’s doing, if you show up with curiosity and a passionate engagement, people won’t notice your wrinkles; they’ll notice your energy. People are naturally drawn to energy, positive energy, but also just learning energy.”
She said, “That’s what will help you get a job. That’s what’s going to help you build relationships. Part of that energy needs to be curiosity because if the energy is just sort of, ‘I know it all,’ that’s not going to work.” Yes, showing up, and it’s also showing up against type because when someone thinks you’re over 50, they think you are closed-minded, fixed mindset, not very energetic, not interested in learning something new.
When you’re exactly the opposite of that, especially for young people, what it says to them is “This is not my parent.” [laughter] That’s actually a pretty important thing. I learned that very much. So many people would bring their parents to the Airbnb headquarters, and I’d meet them, and I’d realize their parents are younger than me. It was really helpful for me to show up in a way that surprised people.
Lisa: I love that. It’s so powerful as an invitation for people to express it. The opening frame for the How We Future podcast and Substack was a post I wrote about the importance of hope, hype, and gratitude as renewable resources, this idea that in this time that feels so hard and difficult, that it is a resilient strategy to be hopeful. In fact, we have to be in order to help advance and get out of a place that feels difficult, this idea of hype not being about toxic positivity or being a vapid cheerleader, but being engaged, being energetic, being excited, that that is a uniquely human force that we should hone as opposed to siphon off because it’s not accepted.
The other is gratitude, which is that there’s always opportunities to be grateful and that that can give you energy. When I was listening to you talk about the importance of not being afraid of being energetic, that that is actually a positive force. I was really taken with that, particularly because I know you’re spending a lot of time with our fellow midlife folks, but I’m very privileged to work with young folks in their 20s.
I will say that, particularly coming out of COVID, my colleague talked about experiencing students as having a crisis of enthusiasm. There was energy, but there was energy around outrage; there wasn’t energy around joy that felt socially acceptable. That was just not the currency of the moment. We almost had to reteach them that it’s okay to feel excited about something. I’m paying a lot of attention to that, to creating conditions to make it okay to experience positive joy.
Chip: Yes. Love that. Love that.
Lisa: Well, I know we’re getting to the end, but there’s just one more big topic I want to cover with you, which is your just tremendous book. I love this so much on Emotional Equations. Chip, I think this is a game-changer. I know you wrote this over a decade ago, but I’ve returned to those equations again and again. Again, I’ll call for just even the metaphor of using equations to talk about emotions.
It’s unexpected, but has so much truth to it; it has so much weight to it. You even talk, you open up about the metaphor of gravity, that gravity is a pull, but we have this emotional weight and this idea that when we understand our emotions, and we put them in the form of an equation, now we can play with the variables a little bit, so it’s an empowering move. I wonder if you could just talk a little bit about how you came up with that concept.
Chip: The origin story on that was after my flatline experience, which happened after I gave a speech in St. Louis, weirdly enough, I had Viktor Frankl’s book, Man’s Search for Meaning, in my day pack. As I’m flying home after they did all the tests on me to figure out what was wrong, I was reading Frankl’s book again. Frankl was a Jewish psychologist in Vienna and ended up in a concentration camp.
He had a theory, which was called logotherapy, which is meaning is the fuel of life. Then he was able to test that theory in the worst of circumstances. What came out of that, reading the book again, this time with a whole new pair of glasses because I had just died, was this idea of despair equals suffering minus meaning. It was that equation, the idea that maybe suffering, if you have a little bit of Buddhist tendencies, the first noble truth of Buddhism is, suffering is ever-present.
It means suffering is part of life. Suffering is a constant, but despair and meaning are inversely proportional. What that means is the more meaning you have, the less despair you may have. That’s at a time when I was really struggling in my late 40s. That was my daily reminder, like a mantra, of “Despair equals suffering minus meaning. Where’s the meaning in this?”
As I got further into it, I started talking to social scientists and started creating other equations, like disappointment equals expectations minus reality. Anxiety equals uncertainty times powerlessness. They’re not all negative emotions, but two-thirds of them are. The focus was like, “Okay, if you can understand the recipe of an emotion, then you can understand how to work with that emotion a little bit more effectively.”
That’s really how the book came about. Yes, it became a New York Times bestseller. What was beautiful about that, Lisa, was I wrote that book as the first book I wrote after having written three books prior to selling Joie de Vivre, my boutique hotel company. I had wanted to become a writer and a speaker even more seriously. The first book I wrote after I left was my first New York Times bestseller.
It’s not my favorite book. I’ll be honest, it’s not. It’s the book that, in many ways, helped propel me forward in terms of people saying, “Okay, who is this Chip Conley guy?”
Lisa: It’s a book I return to again and again. It helps me make meaning. Particularly, that last one that you talked about is why I started How We Future, because I just realized that there was so much anxiety that didn’t have a place to go, so this idea that anxiety equals uncertainty times powerlessness. In a world that’s moving as fast as it is, we don’t necessarily have control over the uncertainty, but the powerlessness we could really examine.
Not only can we decrease our feeling of powerlessness, on the inverse side, how do we increase our feeling of power? I don’t know about you, but I didn’t take a class on power. It’s motivating me to want to create one. I’ve had a great pleasure of working with folks, Jeff Pfeffer, who’s written about power, Eric Liu, who talks about power. I’m a huge fan.
Chip: Dacher Keltner from UC Berkeley writes about it as well, yes.
Lisa: It’s one of these things like, “Oh, it’s uncomfortable. We should shy away.” So much of, I think, the work that you do in this beautiful way is helping people find agency in their own life, which is a form of power. That is more important than ever because, again, if we look at these variables, if uncertainty promises to continue to go up, I don’t think the world is getting more simple on its own.
What can we do to support each other to build the skills, the mindsets, the way of being in the world that’s going to help us live our best lives and pass it on to our generations? Yes, well, maybe I’ll end here, Chip, with two things. One is returning to this idea of hope, hype, and gratitude, all of which I have for you. In fact, I’ve developed a new thing, I’m starting to dress for my guests.
You can’t see, but my T-shirt says, “Rebellions are built on hope.” I know your first book was all about being a rebel, but I just really want to share tremendous gratitude for you, for all that you’re doing, continuing to push the boundaries, continuing to be hopeful, and continuing to lift up energy as you do it. Thank you so much for being a part of this.
Chip: Well, I feel like I’m dancing with you because you are doing all the same things, the positivity that you have, again, with a grounded positivity. That’s really the key. There are people walking on air, but most of us can’t do that, and most of us can’t do that for very long. I just want to say thank you to you.
Lisa: Aw, it’s wonderful to have you.
Thank you, Chip, for being our first guest of Season 2. As we start off 2026, I invite you to notice where you can bring a little more curiosity, generosity, and joy into the room. If this episode resonated, please share with others and leave a review for How We Future. It really helps these conversations reach more people. I’m Lisa Kay Solomon. Thanks for listening, and I hope you have a great start to the new year.