The Time of Our Lives

The Time of Our Lives

An Interview With Chip Conley

"Meet Your Maker" by Ryan Dean Sprague /

The new path is not toward retirement, but renewal. What does being a modern elder mean to you?

The Modern Elder Academy is where people learn to embrace their age, their gifts, their wisdom.

MEA’s workshop cohorts offer a powerful sense of connection—a “collective effervescence”—that’s growing into a new kind of worldwide web, led by a man who has lived some hugely successful corporate mantras for happiness and inclusion:

Joie de Vivre’s “Create joy!”
Airbnb’s “Belong Anywhere!”
MEA’s “Minting elders who are curious, wise, playful, audacious, and generous.”

This new path is not toward retirement, but renewal.

Having spent a week at your Modern Elder Academy in Baja, it struck me that a big step to becoming a modern elder happens when we stop resisting who we are and come out and embrace it. That’s when the fun begins. And that got me thinking about two of my best friends from high school and college who are gay. They were in considerable discomfort for years because they were closeted. But there was a point when they came out—and then a point where I got jealous because they were having more fun than I was. I’m wondering how this analogy works for you? Coming out—and coming out as a modern elder.

Good question. I think there’s something to your analogy in the sense that there’s a taboo, obviously, in society around being gay. There’s also a taboo around being middle-aged or being in midlife. No one’s ever brought this up to me before, but it may be part of the reason I’m so attracted to midlife. It’s something that has a besmirched reputation that limits life or is painful for a lot of people—but it’s the best time of my life.

I began coming out in 1983, when I was 22. It was the summer between my first and second year of Stanford Business School, and I was in New York. I was a hyper-achievement-oriented person. I was an All-American water polo player. I was in a fraternity. I had a girlfriend. I was the youngest person in my Stanford Business School class. And the best way to describe what happened the first time I walked into a gay bar was that my life went from black and white to Technicolor. I was like Dorothy in The Wizard of Oz when her house landed on the Wicked Witch. The world suddenly got bright and new. What that moment meant more than anything was the realization that I wasn’t alone.

The idea of coming out with a scarlet letter G wasn’t advisable from my father’s perspective. But I think what it did is that it allowed me to really sink into the depth of who I was. Some of it had nothing to do with my sexuality. Some of it had to do with my curiosity about spirituality. Some of it had to do with my fascination with the mystics. What was interesting, and I think is sort of weirdly ironic, is that my coming out process was also a coming out spiritually. I grew up in a conservative Episcopalian family that was basically non-religious, and I got really curious about spirituality right around the same time I came out. I think it had a lot to do with trying to understand the mystery of life, including the mystery of why someone is gay or not. Modern science still hasn’t figured that out.

And you felt a lot more joy?

Yes. In many ways. I broke out of my straightjacket that had defined me. <laughs> Midlife can be like that in a way, too. By midlife we tend to have figuratively piled on so many sweaters and coats that we’re weighed down by our uniforms. We need some space to disrobe—to re-embrace ourselves. I realized I wasn’t alone in that either.

Let’s come back to that. Your big success early was a hotel company called Joie de Vivre that grew to 50 boutique hotels. But you started with one hotel that rented by the hour in the Tenderloin. That first hotel sounds like another besmirched reputation.

That’s true. My first hotel was called The Phoenix, and it did rent by the hour when I bought it—and it was failing. But I thought The Phoenix could rise from its own ashes as a rock ‘n’ roll hotel. I’m a Scorpio, and scorpions are very phoenix-like. And the phoenix is the official bird of San Francisco because the city came back to life from the 1906 earthquake and fire. I was 26 when I resurrected that hotel and launched Joie de Vivre. My experience coming out made the company name and the idea of embracing a joyous life visceral for me. It was our mission to create joy, first for our employees and then for our customers. That mission just kept growing.

You were on the board of the Esalen Institute for 10 years. What got you there?

The first time I went to Esalen was with my girlfriend in college, and we tried to sneak into the baths. But we couldn’t. The second time was right after I’d come out. I was really curious about the Human Potential movement, about Abraham Maslow and all the great thinkers who had been there. I ended up going back over and over again. I learned to meditate there. I learned to love massage. Then I started teaching workshops once a year. And then I joined the board and became one of the biggest donors. The bookstore at Esalen is named after me.

While we were in Baja, you spoke about the Great Recession. You lost a bunch of your friends to suicide. You sold your hotels.

The Great Recession was punishing for all kinds of people. All five of those friends were men between ages 42 and 52. So they were in early midlife or midlife. Three of the five were entrepreneurs, and their businesses went belly up. Their sense of self-esteem was so attached to their business cards that the Great Recession revealed their lives as a house of business cards. It all crumbled.

I went through my own Dark Night of the Soul. So many things at once. A long-term relationship ending, not by my choice. An African-American foster son going to prison as an adult, wrongfully—I got him exonerated. My company was running out of money, and I didn’t even want to run my company anymore. I also had some health stuff going on, and then I had an allergic reaction to an antibiotic and flatlined several times. That flatline experience turned out to be my wake-up call.

Looking back, I was 47 years old when I hit bottom. I had never heard of the U-shaped curve of happiness, which shows, as you know from the workshop, that the low point of life-happiness globally on average is 47 years old. That period of my life—from, say, 45 to 49—was definitely my darkest time. But it helped set the table for my curiosity about the period of life that we call midlife. That time has a bad brand attached to it—as if it has to be a crisis. I went into my fifties, and it was the best decade of my life.

You went to work with Airbnb and became the elder mentor of a group of twenty-somethings. Airbnb’s motto—”Belong Anywhere”—sounds like part of your story. Did that come from you?

No. “Belong Anywhere” wasn’t my idea. But it came out of a process that we used at Joie de Vivre and now at MEA. The process involves repeating the same question five times where you can’t give the same answer twice. The question was, “What business are we in?” and the series of answers got us to realize that we weren’t in the home-sharing business, we were in the “Belong Anywhere” business. That was our core, our soul, our essence as a business. That process led us to reorganizing the company around that two-word mantra, “Belong Anywhere.” It’s another way of saying you’re not alone.

Then you left Airbnb and built a magnificent beach house in Pescadero, Baja, that gave birth to the Modern Elder Academy. How did that happen?

I’d come down here to southern Baja with a couple friends a dozen years ago. I was here for a week, and with each day I appreciated it more and more. There are some places you go that immediately give you a hit, but then it wears off. The experience here was something that built with each passing day. I think it was the magical nature of the nature here—as well as the culture I loved. And so, after coming down here a few times, I decided to buy a home and completely redo it.

Then I began writing the book, Wisdom at Work: The Making of a Modern Elder, based upon my Airbnb experience. And while I was writing the book, I was going for runs on the beach. That’s when I had a Baja “Aha!” My epiphany was to realize that we don’t have midlife wisdom schools. We don’t have what Mary Catherine Bateson calls a “midlife atrium,” a space for some light and some clarity. And it suddenly struck me that I could create something like that: a physical space that has a curriculum that helps people to reframe their relationship with aging and to cultivate their wisdom. My hotel experience, Airbnb, Esalen, mentoring—it all clicked together into what I dreamed of doing next. And I started MEA with my two co-founders, Christine Sperber and Jeff Hamaoui. And we started adding guest rooms and meeting rooms and a yoga platform to my beach house. I had to buy myself a new house down the beach.

One of my friends is an Olympic gold medalist from Germany, and his coach would assess other athletes and say, “This guy has stopped learning. You can beat him.” So my friend’s program for winning the gold medal was based on continuous learning. MEA is also based on continuous learning. What’s the difference?

MEA’s curriculum has multiple parts to it, but one key piece is the idea of moving from a fixed mindset to a growth mindset. A fixed mindset is focused on proving yourself, and you define success as winning. So an Olympic gold medalist would be continuously learning their craft to win.

A growth mindset is not about proving yourself. It’s about improving yourself. And it’s not about winning. It’s about learning. And when you take a growth mindset to your life, and especially to aging, it opens you up to becoming a beginner again, to being curious again, to really wanting to learn again.

Many successful people in midlife have been on the treadmill for so long and they’ve been running so fast that they feel that whatever they do, they have to do well. That makes it really hard to start something new. Either you are not patient enough to learn it. Or you’re so self-critical that you get upset at yourself and quit. One of the things we love about MEA is that we create an environment where people learn how to be open to new experiences again. They learn to enjoy being beginners again. Openness to new experiences correlates with living a long, happy, healthy life, and I think MEA is the ultimate taproot for helping people to find that curiosity that opens them up to new experiences. That’s one big reason we offer surfing lessons at the end of the week. We call this kind of midlife education “long-life learning,” how to live a life that’s as deep and meaningful as it is long. We have more than 3,000 alums from 42 countries and 26 regional chapters around the world. We appeal to a diverse demographic partly because we offer financial aid, which is unusual for retreat centers.

One of the first things I noticed at MEA were the hot tubs and the wine.

<laughs> Yes. Some retreat centers are great, but very Spartan, and there’s a time and a place for that. If you’re doing a Zen meditation retreat, there probably should not be any wine around. But we want to celebrate, we want to be playful, we want to have fun. There’s some great learning to be done, but we don’t want a person to feel like this is work. We want this to feel like a wellness vacation, and we really want to deepen connections, where almost every conversation is from what we call the third vault, a heart connection. So, if you do drink alcohol, you are probably going to want a margarita while you’re down here—but we also have some alcohol-free weeks, too. And most people do end up in the hot tubs.

There are five adjectives that define the brand of MEA: curious, wise, playful, audacious, and generous. That is what we try to create with the environment that is MEA. But those five adjectives also define the way we think a modern elder can be. Part of our job at MEA is to mint modern elders who are curious, wise, playful, audacious, and generous.

I was intrigued by MEA’s twist on name tags. Instead of being issued a name tag, we each chose tags that revealed something personal about ourselves. One of four tags I chose read, “I secretly believe in magical thinking and am embarrassed by that.” Another tag I wrote for myself read, “I feel like I don’t belong even when I do.” Then we had an exercise that involved reading one another’s tags. It was a little unnerving, but everyone did it, and it created a deep bond in the group within the first 24 hours.

That first exercise is part of all of our workshops. Each person, no matter what the particular curriculum happens to be, is on a hero’s journey—a journey that the entire group also goes on together. And one goal of the journey is to get to know people from the inside out. So, instead of sending every participant an email that says, “Here’s a list of all the people who are coming to your workshop and their LinkedIn profiles,” and then providing everyone a name tag on arrival, we do the opposite. We don’t even want you to know each other’s last names—not at first. We don’t necessarily want you to know each other’s careers. And if you want to use a different name, you’re welcome to use a different name. As I said before, one of the beauties of MEA is the disrobing of identities. One goal is to let you try on a new identity and mindset for a few days and regain a sense of who you are without all of your habits.

One fundamental issue in America—especially as people get older—is loneliness. Just the ability to meet that many new people and potentially make new friends is remarkable. I live out in the sticks in Oregon, and I think that made my group especially good fun.

That is not something that we lead with, but that’s certainly a part of MEA. A recent study found that two-thirds of Americans are in search of deeper, closer friends. The key words are “in search of.” It’s not just that they’re open to closer friends; they’re actively in search of closer friends—for very good reasons. An 85-year longitudinal study of adult development from Harvard found that having strong social relations and “emotional insurance” at 50 is the best predictor of happy and healthy living at age 80. The number one variable for having a good, long life is your relationship with community. And so we certainly help provide that—even to people who don’t know they need it.

You also have a very active MEA alumni network. My group, my cohort, had its first post-workshop Zoom, and almost everyone showed up. And there’s an ongoing group chat on WhatsApp.

Most of our graduates feel a sense of community with their cohort—the people they were in a workshop with—but also with a broader collection of people in the MEA community. I think one of the reasons it works is because we have a common curriculum and MEA workbook, so there’s a common ethos across all of our alumni. The week that you were there, Steve, the focus was on wisdom, but there’s a core curriculum across all the workshops such that when you get two MEA alums together, there’s a common language. There’s even an MEA regenerative community of 26 alums living around a regenerative farm, and we’ll be opening two larger campuses in Santa Fe, New Mexico, in the next couple years, as well as more regenerative communities. It feels like MEA is creating a global movement of inspired and empowered midlifers who are learning from each other as they grow into modern elderhood.

Join Us in Santa Fe When S+H Goes to MEA…

In 2024, MEA will be opening a new campus outside Santa Fe, New Mexico, at a spectacular 2,600-acre regenerative horse ranch. MEA chose Santa Fe for their U.S. headquarters because of the long history of being a place for personal growth and connection, the history of indigenous eldership, and the opportunity to use nature as a teacher.

Santa Fe is also home to lots of S+H subscribers, so we’ve decided to create a gathering called “Spirituality+Health in Midlife & Beyond” from March 24–31, 2024. The group will be facilitated by Chip Conley and Steve Kiesling, who created this interview. But we expect everyone to be teachers. We’ll be gathering to learn, to share, to experiment with regenerativity, and to have a very fine time in a beautiful new place. We’ll also practice interviews—including interviewing yourself on your own heroic journey. If you would like to stay updated on the upcoming details of this event, please go to

Not yet part of the Spirituality+Health community? Celebrate 25 years of S+H by subscribing here.

Meet Your Maker Elder credit Pavlov Visuals

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