Embracing Midlife: Wisdom, Growth, and Reinvention With Chip Conley

Chip Conley: 09:58

We need more hosts. We need more hosts. And so, you know, me coming in and saying, well, I wasn’t using the word friction. I didn’t really understand that word until I was in the tech world. I understand friction means you add something that might actually reduce your growth.

And so you don’t want to do that. But at the same time, if the friction is something that’s going to improve quality in the long run, that could improve growth because it means we have better hosts and better hosts mean a better experience, which means more guests are going out and saying good things about us. So. So that kind of philosophical business question came up a lot because my point of view was. You know, I have to be the Bible thumper when it comes to quality.

And that’s why you want me here. And the good news is, in the long run, I was able to show data. And that’s a big thing in a company like Airbnb that showed persuasively that our growth was being enhanced by the quality of hosts. So improving the quality of hosts was a really important metric for success for the business.

John Corcoran: 11:10

What about you personally? You’re someone who, when you joined Airbnb, up until that point, your entire career had been focused on hospitality and then you joined this company that is basically, you know, many have said is disrupting hospitality. Were there peers, old contemporaries of yours in the hospitality world that were like, Chip, what are you doing here? Why do you like dancing with the devil?

Chip Conley: 11:36

There’s a Gandhi quote, which is something like, first they ignore you, then they ridicule you, then they fight you, fight you and then you win. I used to say that quote in Airbnb a lot when I joined, I was like, first they ignore you. That was true when I joined Airbnb. Yes, I was one of the most well-known boutique hoteliers and everybody thought like, I’ve never heard of Airbnb. What the hell is that? That doesn’t make any sense. Then they ridicule you because actually we started to get on their radar. So I joined in early 2013. By 2014, we were more on the radar. So ridicule started.

Then they fight you. And of course, that was a big part of the thing. And then and then you win. And then at the end when we had our IPO and became the most valuable hospitality company in the world, that was sort of a win. Having said that, I did have some people say, you’re Darth Vader, Darth Vader going to the dark side.

And yet most people in the hospitality industry were very curious about what the hell I was doing. And as one of the first boutique hoteliers, which meant I was a disrupter before I was a boutique hotelier in some ways. I think people were interested to see, like why I had chosen to go on this path. In the end, I mean, I feel very redeemed by the fact that the company did as well as it did. And has done as well as it’s done.

But yeah, some said, like, you know what, what are you doing here? And I guess what I would say to some of those people back then was, listen, I joined the hospitality industry as a young entrepreneur who loved hospitality, loved the idea of taking care of people. And I loved the fact that it was an entrepreneurial business. By the time I’d sold my business, 24 years later, the entrepreneur, the entrepreneurship of the business had turned into private equity firms who were coming in and buying and seeing hospitality as another class of real estate. And I felt like we’d lost some of that entrepreneurship.

Airbnb is, in essence, democratizing hospitality and allowing lots of entrepreneurs around the world in, you know, 194 countries to learn how to become a hospitality entrepreneur. I’m going to support that. I’m going now because of what needs to be, you know, how we regulate and tax this activity, which I from the very start said to the Airbnb founders, dudes, if this continues to be as successful as you are there, you have to be regulated. You have to be taxed because that’s the only way you’ll ever be legitimate. And so that was a hard one for them to hear. But ultimately they saw that it was true. And I wasn’t always right. I was wrong a lot. But you know, that was right there. And, you know, with some of them in the hospitality business, there are a couple.

There were a few people who were like, yeah, they were nasty to me. But I was invited to hospitality conferences all the time, and I received a lot of resumes from people in the hospitality business. They said, I want to get the kind of stock deal you’re getting. So yeah, there was a little bit of envy I think as well.

John Corcoran: 15:02

Yeah. That’s cool. So what I want to know is, you know, at what point in this journey did you, you know, you’d been learning, you’d been mentoring you, giving and receiving at Airbnb. And at some point you decide that I want to take this further. I want you’ve research on aging.

You’d realize that there are probably many of your peers that weren’t having the same experience as you were. You know, you know, maybe they were feeling irrelevant at this point in their career and their trajectory. At what point did you decide, you know, this is kind of calling me to create something that’s going to help others.

Chip Conley: 15:39

Yeah. To create the world’s first midlife wisdom school. You know, I think that’s part of what. Where were the seeds of this? My process in my 50s. My late 40s had been a real struggle for me. I really wanted to sell my company. I, unfortunately figured that out during the Great Recession. So that was not the right timing. And I had to sit in my saddle as CEO of that company for two years of the Great Recession. And, you know.

John Corcoran: 16:05

Just a really tough time. Yeah. Yeah.

Chip Conley: 16:08

Very, very tough time running out of cash, etc.. So long story short, I’d seen midlife as a crisis. And then I went into my 50s and, and enjoyed my first two years after selling my company, had some space in my life, then joined Airbnb at 52. And I now saw midlife as a chrysalis, midlife being that transformational life stage between the caterpillar and the butterfly when you’re in a cocoon and it’s like, oh, wow. You know, on the other side of the cocoon is that butterfly.

And maybe on the other side of me, you know, going through the hard times I went through was like, wow, I feel really great in my 50s. I hadn’t heard of something called The U-curve of Happiness, which shows that 45 to 50 is the low point of adult life satisfaction. And after 50 we get happier and happier with each decade. So as I’m learning about this stuff and making notes about my experience at Airbnb and I, by the time I joined Airbnb, I had written four books, I guess. Yeah.

And so I was, I think, starting to percolate a book in my brain. And so I spent four years full time there, but I didn’t want to spend any more full time there. I loved it, but I wanted to spend my last three and a half years there in a part time role, because my original intent in joining Airbnb was to be part time, and it became full time within weeks just because it was clear they needed me more than I thought. And long story short, as I went from full time to part time, I moved down to Baja part time, which is where I am right now, which is where our first MBA campus is. And I started writing this book, Wisdom at Work: The Making of a Modern elder.

As I was writing that book, I came to this conclusion like, wow, this is interesting. I think there is the opportunity to create a like a center, a retreat center where people come and spend a week learning how to become a modern elder, learning how to be curious and wise, how to reframe and recast their career, how to learn something new, how to navigate transitions in midlife, how to cultivate purpose, how to actually learn, how to cultivate and harvest their wisdom and and maybe reframe their relationship with getting older, and all of that led me to creating me, the Modern Elder Academy, the world’s first midlife wisdom school. Now we have two campuses at this point, a beachfront campus here in Baja, and then a 2600 acre regenerative horse ranch in Santa Fe, New Mexico. So, you know, we have had 6000 people go through our program and graduate there from 60 countries. We have 60 regional chapters around the world.

So it’s a bit of a movement, and I’ve loved it and I’ve been doing it now for seven years. And I think if I have one key lesson in this is that, you know, our best years may be ahead of us. And as it turns out, for me, my 50s were my best year in my career. I’m now 64 and I’ve enjoyed my 60s as well. But the key is to learn how to shift your mindset from a fixed to a growth mindset in ways that allow it to be open to new opportunities.

John Corcoran: 19:37

And that’s easier said than done for someone that’s had that fixed mindset for, say, 30, 40 years. So how do you tap into that? Someone who comes to one of your retreats and, you know, has been the way that they have for a long time?

Chip Conley: 19:51

Well, we have them do a little homework before they come. So that gets them in the right mindset. But we also help them to see the downside of that fixed mindset. First of all, there’s all this research that shows that if you shift your mind, your mindset about aging from a negative to a positive, which is not easy to do, because generally the societal mindset on aging.

John Corcoran: 20:17

Is overwhelmingly. Negative. Yeah. Yeah.

Chip Conley: 20:19

But if you can shift. From negative to positive, you’re what? And do that in a sustained way. You gain seven and a half years of additional longevity, which is more additional longevity than if you actually stop smoking at 50 or start exercising at 50. So helping people to see like, wow, there’s longevity benefit to this. Helping them to ask the question ten years from now, what will I regret if I don’t learn it or do it now?

And what do I regret that I know now that I wish I had done ten years ago, or learned ten years ago. These are the kinds of questions that help people to wake up, to realize, you know what? I am a little stuck. Or I am a little bit bored, or I am a bit bewildered or disillusioned. And I actually, you know, I can’t wait around to learn. As I learned when I came to Baja. I was like, okay, I am in a fixed mindset that I can’t learn Spanish. I’m too old. I’m 56, 57 years old. I can’t learn how to surf.

But when I put it in the frame of like ten years from now, what will I regret if I don’t learn it or do it now? I regret that I didn’t learn Spanish. I’ll regret it. I didn’t learn to surf. Serve. And so I started to learn those things. And so we helped create a method for people to learn how to become a beginner again.

John Corcoran: 21:40

I want to ask about your health journey because, you know, around the I think a couple of years into running the school, you ended up getting diagnosed with cancer, which you continue to battle. And you had this just strange confluence of events. You were publishing your book. You were on the Today Show. You’re going through chemo, all this. This was all happening, I think, about a year ago now or something like that.

Chip Conley: 22:08

So yeah. So I had a book called Learning to Love Midlife 12 Reasons Why Life Gets Better with Age that came out a year ago. And I bought that at that point two years ago. So six years ago I found out I had, you know, early stage prostate cancer. Didn’t worry too much about it.

And then it went to the second stage. Then it went to the third stage. And so in preparation for a year ago when the book was coming out, I had a book coming out and a three month book tour, including being on the Today Show and Good Morning America on back to back days. I had our Santa Fe campus launching during the same time. I was doing a reorg of my company in terms of shifting the leadership team and ultimately elevating our CMO to become CEO.

All of this was happening at the same time as I’m doing 36 radiation sessions, hormone depletion therapy, such that I had virtually no testosterone for two years and two surgeries. Ultimately having my prostate taken out. So yeah, that was a lot.

John Corcoran: 23:17

And yeah.

Chip Conley: 23:18

Thank God I meditate because my meditation practice was the thing that grounded me. Thank God I had a lot of good friends and a great team at MTA. And I had just this belief that, you know what? On the other side of this, I can look back on this and I will. I will feel like my painful life lessons will be the raw material for my future wisdom.

And I, I think for all of us, I am just a role model for what happens at MTA is a lot of people come there, you know, limping in, you know, you know, dealing with a divorce, dealing with a business that went down, dealing with, you know, fears of retirement, dealing with parents passing away empty nest, you know, a health diagnosis. And they’re feeling somehow like they’re stuck in the chrysalis, they’re stuck in the cocoon and they’re never going to get out of it. And I and I just wanted to use my, you know, unfortunate circumstances as a role model for others to realize I’m going to get to the other side of this, and I and I have and yes, I still have cancer inside me. I still have stage three cancer in my lymphs. So, you know, I mean, who knows how long I’ll live?

Likely. Likely. You know, at least ten years, probably. Maybe 20, maybe 30. And what it does is it helps me to, you know, death is a very, you know, exquisite organizing principle for how you live your life. And so I live my life, as Gandhi said, I’m quoting Gandhi twice on this podcast. You know, live your life as if this year may be your last. Learn as if you’re as if you’re going to live forever. And. And that’s what I’ve tried to do.

John Corcoran: 25:14

Yeah, I can’t help but ask. The title of the book is Learning to Love Midlife 12 Reasons Why Life Gets Better With Age. And I read that and you seem like an overwhelmingly positive guy. But after that story you just told about the Today show and all the treatments and all that kind of stuff, is there anything you would have done differently, whether it’s a different title or approached the book any differently, given what you know now?

Chip Conley: 25:41

I mean, I think that the book has a pro-aging message to help people understand. Like, yes, some things get worse as you get older, but there’s a lot of things that get better. So I wouldn’t take anything away from that. I think the word midlife scares people. They hear the word midlife.

They think about the crisis. They don’t know what midlife is. You know, in my opinion, midlife is 35 to 75, so it’s a very long bridge. So I think midlife sometimes as a word can be frightening. You know, I think the book is, you know, became a bestseller. So it clearly, you know.

John Corcoran: 26:15

That word didn’t sink it then.

Chip Conley: 26:18

Yeah. Yeah. So it resonated with people and it got a lot of attention. And I would say one area I wish I’d spent more time in the book is how men versus women deal with midlife? Men’s biggest fear in midlife tends to be being on the path to irrelevance. And for women, it’s being on the path to invisibility. And they’re slightly different issues. They’re involved in that. And so I do address that in the book, but not as much as I could have. So but yeah, I’m, you know, I’m proud of the book I have. I’ll have more books coming out. This is my seventh book. So yeah.

John Corcoran: 26:57

Yeah. How did you come up with the curriculum for the academy? For school? Like, there’s I mean, it’s such a broad topic. There’s so many different things. And do you cycle through different curricula, or do you try to give each group that comes in the same experience?

Chip Conley: 27:13

You know. Each week is different. It’s a workshop, you know, so there’s, you know, over the course of about 120 workshops a year, and maybe out of those 120 workshops, about 40 different titles. So there’s a lot of different choices. Some of them are the same. So we have navigating transitions and cultivating Purpose. Those are two of our most popular workshops and are sort of our baseline.

We have something called owning Wisdom that’s also quite popular, but we have a lot of well known, well known faculty. You know, everybody from Elizabeth Gilbert who wrote Eat, Pray, Love. Dan Buettner, who wrote Blue Zones. You know, we have Arthur Brooks, you know, from Strength to Strength. Blake Mycoskie who started Tom shoes. So we have a lot of different faculty members who come and teach with us. And so we have lots of people who come once a year because they’re not going to repeat themselves. They’re going to like it.

Chip Conley: 28:14

Each workshop has a certain amount of core content for me, but also has a slightly different theme or flavor, but we really worked closely with academics at Stanford, Harvard, Yale, and UC Berkeley to help craft the curriculum. Yeah.

John Corcoran: 28:31

So and what does someone like that who I guess this question could apply to you as well, but someone who’s achieved a lot in their career, what is the the selling point for them to come to an academy like that and teach a group of people about what they’ve learned?

Chip Conley: 28:47

You know, it’s interesting because, yeah, almost nobody’s doing it for the money. Because these are small workshops, usually about.

Chip Conley: 28:55

Two dozen people workshop. I think they’re curious. First of all, our two campuses are exquisite.

John Corcoran: 29:03

Beautiful places. So that helps.

Chip Conley: 29:06

Yeah. Like you’re getting free. Accommodations and great food. We have like, people. It’s been described as MTA has been described as Four Seasons meets the Blue Zones, meets the Esalen Institute, the famous retreat center.

Chip Conley: 29:21

In Big Sur. Yeah. So, you know, it’s a pretty, pretty damn good experience. But I think they’re really really interested in the topic. I mean, this idea of longevity, this idea of curiosity, the idea of how do we help people reframe themselves in midlife and beyond. Is interesting for some of these people in their own lives. And so they come to it knowing that this is a place where they’re going to learn something as well.

John Corcoran: 29:52

And one of the most powerful things I saw, one of the presentations you did was that in the last 100 years, we’ve added 30 years of life expectancy. That is just a monumental shift for the human race in 100 years. Such a short period of time.

Chip Conley: 30:10

You know. When we look at things like, what are the inventions of the 20th century? Rarely does someone talk about longevity as being an invention, but it has been an invention. You know it. To have added three decades in one century means that, you know, retirement all of a sudden became a thing. It means that midlife became a thing because midlife didn’t really exist prior to, you know, the 1930s, 40s and 50s.

And so we’ve really completely changed the modern life cycle of how people live their lives. And we have yet to, I think, as a society, help people understand what does that mean for how you how you’re going to operate, because you’re probably going to operate and live your life into your 60s, 70s, 80s and 90s different than your parents or grandparents did. And therefore, we need schools to help people with that. And also, you know, if you think like you’re going to fuel up the tank of learning and education at age 18 to 22 in college, and then you’re going to drive that tank of gasoline for the rest of your life. You’re going to learn that at age 50, you’re running on fumes. And the world has changed a lot. And so you need to refuel. And so me is a bit like an educational pit stop for someone in the middle of their life.

John Corcoran: 31:34

What if you could wave a magic wand and make any change? You know, whether it’s like, everyone would go through some kind of, you know, midlife academy type of thing? You know what? What kind of changes would help society to prepare for this profound change that we have experienced?

Chip Conley: 31:54

I mean, if I had just one, I could have many, but if I had just one, it would be to culturally shift the norm such that at age 50 or between ages 45 and 50, that we as a society believed that everybody should take a minimum of a three month sabbatical.

John Corcoran: 32:19

Like a gap year, but. A gap year. I’d like to see. I’d like it to be a full year.

Chip Conley: 32:23

Yeah, but I also want to be recognized that, you know, it may not be able to be. So it may be like we have this thing, you know? 529 you’re like, help to like, save it for.

Chip Conley: 32:33

For yeah, for your. Kids. Well, how do we help people to do that for themselves?

John Corcoran: 32:37

Yeah.

Chip Conley: 32:37

How do we build that into a career path such that between 45 and 50, you don’t feel a little embarrassed that in your resume you took a year off?

John Corcoran: 32:46

Yeah.

Chip Conley: 32:47

No. You like it’s expected. I mean, it’s like in Australia, it’s expected when you graduate from college that you’re going to take a gap year and travel around the world.

John Corcoran: 32:57

It’s part of.

Chip Conley: 32:58

Culture. So, you know, or in Israel the culture is you’re going to go into the, the, the military. Everybody does. So I just think that that would be a really helpful thing because it would help people to have the restart button pressed in their life.

John Corcoran: 33:16

Yeah for sure. Chip, this has been fascinating. I want to wrap with a question that I asked Tony that led me to you, which was who out there, you know, do you admire and respect? Do you have any peers or contemporaries that you know you would want to acknowledge and just thank for being there for you throughout your journey, throughout your lifetime, throughout your career?

Chip Conley: 33:37

I mean, Danny Meyer, I will say, is somebody I really admire. He’s maybe the best known hospitality person in the world. He wrote a book called Setting the Table. And he’s a restaurateur, so I’m a hotelier. So we actually had a nice friendship because we sort of come at things from two different directions in the hospitality business.

But he really has more than anybody else in my industry, helped elevate the conversation to help people, to see that hospitality can be offered in any industry. It’s a way of being in the world as opposed to an industry. You know, you just go to Cornell to learn the hotel school. So I have a lot of admiration for how he’s run his business and grown his company.

John Corcoran: 34:25

And where can people go to learn more about you and to learn about attending one of the workshops?

Chip Conley: 34:32

Yeah. ChipConley.com. Or the MEA website is MEAwisdom.com. And I have a daily blog that you can find at either of those sites called Wisdom Well. That’s free and you get a if you sign up for it, it’s you get a free micro dose of wisdom every morning from me by email.

John Corcoran: 34:53

Awesome. Chip, thanks so much. Thank you John.

Outro: 34:58

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