The 'Great Midlife Edit': Master your middle years | Chip Conley | Big Think Edge

Welcome to Big Think Live. I'm Peter Hopkins, president and co-founder of Big Think. Today's topic is "The Great Midlife Edit: How to Master Your Middle Years." Our guest today is the entrepreneur and sage Chip Conley. He is a hotelier, New York Times bestselling author, social alchemist, disrupter, student, and modern elder. Chip is the hospitality maverick who helped Airbnb founders turn their fast-growing startup into the largest global hospitality brand.

In his most recent book, "Wisdom at Work: The Making of a Modern Elder," Chip shares his unexpected journey at midlife, from CEO to intern, learning about tech at Airbnb's height of global hospitality and strategy, while also mentoring its CEO, Brian Chesky. Chip is also the founder of the Modern Elder Academy, which we'll be talking about a bit later, where a new roadmap for midlife is offered at a beautiful oceanfront campus in Baja California Sur, Mexico, from which Chip joins us, in fact. He also finally serves on the board of Encore and the advisory board for the Stanford Center for Longevity.

Chip, welcome to Big Think Live.

Chip: Peter, I just found out you were down here in Baja just as the pandemic was kicking in. I wish you'd stayed!

Peter: Me too! Me too! Definitely better than doing quarantine in Manhattan, at least during it, anyway.

If you're new to Big Think Live, today's webinar will last about 45 minutes. We'll start with a discussion with Chip, followed by audience Q&A. So, whatever platform you are joining us on—YouTube, Facebook, or Big Think Edge—please ask your questions in the comment section, and we will get to them toward the end of the hour. You can start asking those questions right away, and they'll be fed to me for the Q&A period. So with that, let's get started.

Chip, you know, I think as a sort of precursor to the conversation, I'd love you to orient the audience to your career trajectory because, as recently as a few years ago, you were describing yourself as an intern, but you know, at one point in your life, you were a CEO. So help paint a picture of the path you took.

Chip: Sure, so, in my mid-20s, around 25, I started a boutique hotel company called Joie de Vivre, which means “joy of life” in French, based in San Francisco. I was really in the early stages of the boutique hotel movement in the United States. Ian Schrager and Bill Kimpton had started their hotel companies just before I did, and for 24 years, I was the CEO of that company I founded. We created 52 boutique hotels and became the second-largest boutique hotel brand in the United States, with only hotels in California, though we chose to be just on the Left Coast.

I then realized I didn't want to do it anymore. It was the Great Recession, and I just needed to get out. I sold the companies, Joie de Vivre is now part of Hyatt, but I did keep some of the hotel real estate. So, I still owned some hotels, but just the real estate side. Then I didn't know what was next. There’s a famous movie, "The Intern," with Anne Hathaway. Did you see that, Peter? Maybe not—it's a Robert De Niro film, and basically, Robert De Niro, a 70-year-old intern, joins the young 34-year-old CEO of a tech company. He says, “Musicians don’t retire; they quit when there’s no more music left inside of them.” So I know I had music still inside of me in my early 50s; I just didn’t know who to share it with.

That’s when Brian Chesky, co-founder and CEO of Airbnb, approached me. He said, “I want you to be my mentor. I'd like to have you be my mentor. I want you to be the head of global hospitality and strategy and help us democratize hospitality.” At the time, the company was a small tech startup, and I joined. But within the first week, I realized I was as much an intern as I was a mentor because I had never worked in a tech company before.

Ultimately, we decided I was a mentor-mentor and an intern at the same time. Bryan and I basically mutually mentored each other. I taught him a little bit about emotional intelligence and leadership strategy, and he taught me a lot about digital intelligence. I spent four years there full-time; I had a huge involvement in steering the rocket ship with them, and then for over three years now—almost three and a half years—I’ve been a strategic advisor to Brian and the founders.

That led me to coming to Baja, and we’ll talk about that later in terms of the Modern Elder Academy, also known as MEA.

Peter: How would you characterize this leap? You know, because you were a successful entrepreneur and had made a mark. I loved your hotels and was a patron, so when I heard about it, it dawned on me; you were going to be the Sheryl Sandberg of Airbnb. But that’s not the way you seemed to want to characterize it. Why not embrace that sort of “You’re the adult in the room” motif?

Chip: Oh, they’re all adults, let’s start with that. Yes, yes, they’re Millennials, but they’re all adults, and they’re brilliant; there’s a lot of brilliance there. So what I learned quickly was it was like wisdom and genius. Brian hired me for my knowledge, and about three weeks into it, he said, “You’re in charge of strategy for the company now.” I said, “Brian, I’ve never been in a tech company,” and he said, “You’ll be in charge of strategy for a tech company.”

He says, “Yeah, I like the fact that we hired you for your knowledge, but what we really got from you was your wisdom. You have a pattern recognition of being able to see things before the rest of us can.” So, what I had to do, Peter, was I really had to right-size my ego. I’m not saying that Sheryl didn’t have to right-size her ego, but she didn’t come in with the same circumstances I did.

I was CEO of my own company for 24 years; I really didn’t answer to anyone. Now, all of a sudden, I am mentoring someone 21 years younger than me who’s also my boss. In fact, 40% of the United States has a boss younger than them today. If you’re 55 years old, 70% of us at 55 have a boss younger than them. So, I had to get used to the idea that part of my job was to no longer be the sage on the stage but to be the guide on the side. That really meant that my role was to help be in the background supporting Brian and his co-founders to be as successful and effective as they can be.

I’ll never forget the first time I did my first performance review with Brian. He sat down, and it was a very good performance review. The number one negative thing he said is, “You’re reluctant.” There was a reason I was reluctant; I didn’t want to work 70 hours a week. I was supposed to be doing a 15-hour-a-week thing, but one of the things he gave me in the review—it was clear he didn’t have a lot of experience giving reviews, but he was really smart; he was a fast learner.

At the end of the review, he says to me, “So, Chip, what do you think of what I said?” And I said, “Well, Brian, do you want me to answer as your mentor, who’s helping you be a great leader, or as your director, who had just told us something?” So my relationship was a little schizophrenic at times, but you know that.

I didn’t want to be Sheryl Sandberg—she became CEO of Facebook. I didn’t want to be CRO, truly; I wanted a 15-hour-a-week job. It turned out to be 70 hours a week, and I oversaw about seven different parts of the business. But I did that as part of a collaborative team, and that was really it. I’m not saying that to be humble; I’m just saying that because that’s how we tried to operate.

I would say one of the effects I had there was to create a really strong collaborative team. So, I was one of those team members of about eight or ten or twelve. Yes, I was the only one who was mentoring Brian, and I was in charge of strategy for the company and the only person who had a hospitality and travel background, so I had an outsized role among the ten of us. But, the truth was also I was learning as much as I was teaching.

Peter: Well, on that point, you know, I was always intrigued looking from the outside that situation; it seemed like a very interesting move at the time when it was announced. It made a lot of sense, and sort of intuitively, somebody with your experience who really knew what it takes at the margins to take care of the customer and create a hospitality experience that is memorable and brings you back. You know, particularly in the context of, you know, not having control of the product the way you do.

Tell us, give us a little insight into, sort of on a substantive level, what were you bringing? What did you help inform? And then what did they teach you that helped you sort of rethink hospitality, perhaps, or see it in a new light?

Chip: I remember in the first week, Brian and I were talking to Joe Gebbia, who was the head of product. He told me, “Chip, we have a product.” I was like, “Well, we had a product; I’m in charge of all the hosts around the world, and all the homes.” He said, “That’s not the product. The products are software applications.” This was early 2013, and I lived in Silicon Valley my whole life, but I was not a tech person, so I didn’t really understand the lingo and I didn't understand digital marketing strategy.

But what I did understand was a bunch of other things, and I think probably the predominant learning I brought to the table was psychology. One of the things I really taught the company was we need to help create the incentives for hosts to do a great job, and it can’t just be a mercenary thing. We have to adjust both their extrinsic and their intrinsic motivations.

One of the books I’ve written is called "Peak: How Great Companies Get Their Mojo from Maslow," so I’ve been always fascinated by positive psychology. We set up the systems in place because the challenge we had here was the people providing the service were not people who were our employees, nor did they ever have any hospitality training, nor could we actually force them to have hospitality training, because that would make them employees, and we didn’t want to make them employees. A lot of them are doing it part-time, and they’re all over the world—in 192 countries.

So what we did is we created a set of both extrinsic and intrinsic motivational factors for our host community. One other example of that was amplifying our best hosts and calling them "Super Hosts," and having a set of standards that they are held accountable to, which were the standards that guests appreciated.

We had a way for them to communicate with each other, and we created forums for them to learn from each other. So the hosts were teaching each other, and we vastly improved the peer-to-peer platform. When I joined Airbnb, our Net Promoter Score (NPS) was a good bit below the hotel industry, but by the time I left and moved into a strategic advisor role, our NPS for our guest satisfaction was 50% higher than the hotel industry.

This shows that using psychology, along with good algorithms—in essence, combining algorithms and people wisdom, the psychology of understanding motivations—built into a product platform with a certain amount of gamification can actually create better results.

Peter: It sounds so different than, you know, rarely do I hear positive psychology cited as a motivating framework for any sort of digital technology.

Chip: Well, you know, it was that book "Peak" that I wrote that the three founders had read, and they said, “We want to become a peak company. We like what we read.”

I’m very proud of what Bryan has done in the past few months during a tumultuous period for the travel industry. I think part of the reason he did some really positive things for the people he had to lay off was because he created core values in the culture that were based upon psychology and many of the things that we laid in place together.

Peter: Let’s get into that a little bit because obviously Airbnb, now having become the largest hospitality brand in the world, is also emblematic of the crisis that has befallen it. It has become synonymous with a mighty tech giant that’s been hobbled a little bit. What has that experience summoned in your counseling to Brian and the leadership team, and how does it factor into the larger principles of "Wisdom at Work"? Is this consistent with your thinking there, or is this in some ways an outlier that says maybe some things are beyond wisdom?

Chip: You know, it was the wisdom that... Wisdom is often about pattern recognition. Knowledge is sort of an addition equation; you add knowledge. Wisdom is almost a distillation—it’s a division equation. It takes all that knowledge and distills it down to what’s truly important.

In some ways, my role in the company has been that. I believe that the first half of our life is about accumulating, and this second half is about distilling. So part of my role when I joined Airbnb in early 2013 was to take 30 different strategic initiatives that the company had and distill them down to four. I’d say, “These are the four we’re going to bet on in the next three years.”

As the next two years progressed, we got some new ones. Now, one of the things I had to sort of counsel Brian on—and he was doing it on his own without me—was to say, “We’re in way too many different directions right now. We need to get back to what’s essential.”

What’s essential is that we’re in the business of helping people belong anywhere.

One of the exercises we did when I joined Airbnb, my first month there, we had 12 of us in dyads and we asked the following question: “What business are you in?” So I would ask you, Brian, and Brian would answer. He might say, “We’re in the home-sharing business.” I’d then ask again, “What business are we in?” This time, he couldn’t answer the same way twice.

You do that five times, and you ultimately get to the distillation or the wisdom of what’s your differentiator, what's the essence of your business that makes you different? For us, we’ve learned that we were in the “belong anywhere” business. So I think right now we’re going back to those roots: What does it mean to belong anywhere? How do we actually create the opportunity for people to experience belonging anywhere in their own backyard?

What’s for sure and has been proven is that 60% of everybody’s business today is domestically in their own country, whereas normally it was 45%. It’s often in people’s backyards, so it’s about being a global company but focusing on local because people are focusing on staying near to home.

Peter: In terms of what you took away from the Airbnb experience, how would you distill it from your perspective? What did you take away, and how does that fit into this larger second half editing that you talked about?

Chip: I take away a few things. In the context of companies, I took away the fact that ageism does exist. I didn’t experience it necessarily, but I started to see it in the tech world—not at Airbnb so much, but in other companies in the area.

I think that the future of learning and development will be very much benefited by something like Big Think so that people can actually do their own learning. A lot of it’s going to be mutual mentorship. How do we mentor each other? How do we create mentorship matches such that if I know a lot about how to run a meeting but I don’t know much about, you know, what’s in my iPhone, the company can match me with somebody with whom I can share what I know, and he or she can share what they know? So that was a great learning. I think mutual mentorship is a huge undervalued learning and development tool for the future, especially because it’s very inexpensive—as in free.

The other thing that really relates to this idea that what does it mean to be in a world where we’re going to tend to live longer than our parents on average—maybe ten years longer than our parents. Power in a big digital society is moving ten years younger, as evidenced by tech giants and the average age of CEOs there. The world is changing faster, so if we’re going to live ten years longer, and power’s moving ten years younger, we now have a relevancy gap that’s 20 years long in the middle of people’s lives. And then having a world that’s changing faster just makes people even more bewildered.

I decided to write this book, "Wisdom at Work: The Making of a Modern Elder," while I was writing that book down here in Baja, where I have a home on the beach. I had this epiphany: Why is it that no, there’s no such thing as a midlife wisdom school? A place where people go to actually repurpose themselves and set themselves up for the next era of their life. Because people are working longer and longer.

So I decided to create a beta program for the Modern Elder Academy, also known as MEA, in the first half of 2018, and it was a smashing success. We decided to open to the public in November of 2018 and have now had 750 people from 24 countries go through the program. I’ve had net promoter scores of 94—like off-the-charts scores—and it has been a really transformative experience for all kinds of people. I thought it was just going to be people 45 to 65, but we’ve had people as young as 30 and as old as 88. The average age is 54, and the predominant reason people come is simply because they want to navigate their midlife transitions and shift their mindset about aging.

Because if you’re 54 years old and a woman in the United States and you’re going to live till age 90—which is not unheard of—in fact, if you’re 54 now, the chances you’ll live till 90 are probably about 40%. You’re likely aging. You’re going to live to about 87. So the large chance you’re going to look like 90 and you’re 54—guess what? Jane, who’s 54—you are only halfway through your adult life if you start counting at age 18. Do the math; that’s how it works. So 54 is midlife for adulthood, and it may be mid-career because you might work till you’re 75 or 80.

We do not have schools to help people in midlife reimagine how they’re going to repurpose themselves in new ways, and that’s what we do. It’s really necessary, and of course in the pandemic, we were closed but we reopened in October, and we’re actually developing a digital program as well.

You know, it’s funny, as I was preparing for the interview and getting acquainted with the book, this idea that we’ve arrived at a stage where we just don’t have the cultural equipment, so to speak, to psychologically update ourselves to the circumstances we’re in. To take the skills we do have and repackage them for, you know, not only the moment but for the future, and what came into my mind is sort of the image of people who are not doing this well, you know—finding themselves frustrated or deadlocked in life.

Perhaps you can describe to the audience what are the symptoms? What does this look like and feel like, and how can they know if maybe this is at the root of some of the issues and uncertainties they’re feeling?

Chip: Take a look at the video that led to “OK Boomer,” you know, sort of an older white guy who’s sort of stodgy, basically looking like his purpose in life was to tell younger people how the world works. That doesn’t work in today’s five-generation workplace.

Generally, people who are stuck in midlife—in their 40s, 50s, or 60s—let’s focus—that’s sort of the core of midlife.

There’s a need to be Carol Dweck, the Stanford psychologist, who has popularized the concept of mindset. You could have a fixture of growth mindset in various parts of your life. A fixed mindset generally means you are proving yourself, and the idea of winning is success, as defined by winning, so you tend to focus on the things you do well.

If you have a fixed mindset in adulthood, it means that over time, the sandbox you play in actually shrinks because if you only like to play games that you win, because that’s defined success for you and you’re trying to prove yourself because you think you have a finite amount of skill, you don’t actually try new things. The opposite of that is a growth mindset, and if you have a growth mindset, you’re not focused on proving yourself; you’re focused on improving yourself, and success is defined not by winning but by learning.

One of the qualities that we really try to help people understand is that a modern elder is not just wise; they’re curious. To be curious and wise and to know what’s the perfect alchemy of when you want to offer one versus the other is part of what it means to be a modern elder.

What we really play up is the idea of having an openness to new experiences. Now, that is something that when we tend to think of older people, we often think of people losing that capability, and it is the number one dysfunction for people 55 years and older in terms of a personality trait—the fact that they lose an openness to new experiences. But when you look at the people who are most flourishing at 55 and older, they are the counter of that; they tend to actually be at the standard deviation extreme of their openness to try new things.

So down here at MEA, it means that we help people to try yoga for the first time, or to meditate, or maybe to surf, because we go surfing, or try their hand at poetry or improv or how to actually stack stones. It feels like you’re mentoring the stone because the process of stacking stones is very much like having the presence of mentoring someone younger. So it is a very experiential program built on the premise of baking bread.

Oh my God, I thought when my team said we’re going to have, at each cohort, they learn how to bake bread, it’s like Morgan’s like, “That’s a terrible idea; I don’t want to bake bread.” It’s like, “Okay, Chip, where’s your growth mindset?” Unready!

What we realized along the way—part of what we have to help people do is to let go of what’s no longer serving them, and that brings me to the Great Midlife Edit. One of the biggest challenges people have in midlife is they’ve been accumulating—they’ve been accumulating all this stuff: friendships, boyfriends, girlfriends, husbands, wives, children, roles in work, and responsibilities outside of work.

So you get to age 45 to 50, and you hit this new curve of happiness, which has been proven by social scientists when people don’t have a crisis. Exactly, but what they have is a bottoming out, and what Brené Brown would call an unraveling.

What happens at that point is that people are really well suited to ask the question, “What no longer serves me, and how can I get rid of it?” But we have no social context or any kind of programming that helps people to actually go through that. So that’s actually what we do in our first 24 hours; we help people with their Great Midlife Edit, which is the first step of four steps that we take them through: evolve, learn, collaborate, counsel.

But if you actually aren’t willing to evolve, and we’re going to edit some things out of your life, it’s really hard to give attention to something new. If I had to give advice to someone who wasn’t coming to MEA about this, it would be to make a list of, you know, what are the things in your life that serve you that are actually want to have more of, maybe learn more about. What are the things that just you need to start letting go of, and how do you edit some of those out of your life?

These are sometimes very difficult questions; they're not meant for a 10-minute moment when you’re waiting in line somewhere—though we aren’t in lines anymore, are we, Peter? They're meant for a deeper dive.

But some people can read more about it in my book.

I’m curious how you came upon positive psychology and why it’s been, you know, as a sort of bedrock concept for, you know, it sort of informs a lot of what I’m hearing. How did you arrive on that, and what was the process like—sort of the introspective process of developing this whole program, presumably from your own experiences as well as your research?

Chip: The program has been crafted by a handful of professors from Berkeley and Stanford and UCLA and elsewhere, so it’s been a group effort for sure. But positive psychology has been a part of it—a moderate part of it—for me. I only took one psychology class in college. I went to Stanford, and that one class I took, I remember Maslow. I remember Abraham Maslow, the guy who focused on best practices in human behavior, as opposed to worst practices.

In fact, that made sense! Why don’t we study the people who are flourishing and learn from them and try to do something about it as opposed to study the neurotics and the psychopaths and the homicidal maniacs? I mean, you can’t have too many of those among our more popular topics.

But what I will say is that the process that I went through during the dot-com bust and 9/11 downturn, I had to come face to face with my own existential crisis as the CEO of a company that at that point had been running for about 15 years, and what I came away with was a local Borders bookstore— which no longer exists—and I was in the business section of the bookstore for about 10 minutes. I realized how depressed I was and that my big problems were bigger than just business, so I went to the self-help section of the bookstore.

That’s where I got reacquainted with Abraham Maslow’s books. Maslow was a mid-20th-century psychologist who focused on his hierarchy of needs and the idea that people have some basic needs. Once those needs are partially met, you get to the top of the pyramid and have self-actualization.

What a lot of people don’t know about later in life is that he talked about self-transcendence. So I took that context, Maslow’s concepts of the hierarchy of needs, and I applied it to our company. We tripled in size in a very difficult time, and that’s what led me to writing the book "Peak." That’s what led Tony Hsieh to approach me, and he said Zappos wants to do this. He wrote the foreword to a later edition of the book, and that’s when the founders of Airbnb asked me to join them.

I found that psychology is the most neglected fact—in fact, in some businesses, they’re all human. You know, among our spreadsheets and org charts, at the end of the day, so much of it comes down to the psychology of humans. It’s surprising how little psychology is used on a conscious level at the C-level of most companies.

I like to think of myself as someone once described in an article: “Chip is the crossing guard at the tragic intersection of psychology and business,” and I’ll take that. I’m the crossing guard with my orange vest saying, “Stop! Slow down!”

But it’s served me well. My five books have really woven psychology and business together and entrepreneurship into this, and so I’m a big advocate for us hiring more people into the workplace, as long as those psychologists have a practical perspective on psychology.

Peter: Now before we shift to audience questions, I want to hit a couple more themes from your book. I think you have a lot of interesting concepts that almost are delightful nuggets unto themselves. You make a distinction between lifelong learning and lifelong life learning. Elaborate on that a little.

Chip: It’s a very new idea. I’m working on a white paper, an academic paper with a Canadian professor on this now called “The Emergence of Lifelong Learning: How Midlife Evolved from a Crisis to a Calling.”

The premise is this: Lifelong learning is great. I mean, Big Think is a lifelong learning platform, and I think you lose the 60 years of history. Lifelong learning came about because there’s a premise that you don’t stop learning when you leave college or graduate school.

What you’re going to learn for a lifetime—and learning and curiosity is an elixir for life. What lifelong learning is missing at times is that if I’m doing a job transition at age 30, it’s going to be different than at age 55. Similarly, my sense of what my role is in a company is going to be different at those ages.

Lifelong learning suggests that there’s a lens in which some of the learning needs to happen within—this lens of if you’re in midlife, you’re probably starting to ask questions about, you know, not just retirement but your mortality. You start asking questions about contentment as opposed to happiness.

People who are younger in life are focused on happiness; later in life, we’re focused on contentment. You’re also focused on things like middle essence. Middle essence is the bookend of adolescence. Adolescence happens; you go through physical, emotional, and hormonal changes. Middle essence is when menopause happens for women and andropause happens for men, and you’re going through physical, emotional, and hormonal changes.

I didn’t know about this stuff! Nobody had taught me what it means to be a mentor and an intern at the same time. Nobody had taught me that liminality—which means being in transition—is fine in adulthood.

So part of what we help people to see is that if you’re going to live a life that’s a lot longer than our parents or than you even imagine, and you’re at midlife—mid-adult life at age 54, with 36 years ahead of you, as that woman I mentioned earlier. You better learn how to live a life that’s as deep as it is long.

Lifelong learning is generally about the acquisition of knowledge. Lifelong learning is the distillation of wisdom.

I can go into much more detail about that, and anyone who wants to read about it can read my book or come down to MEA.

But it’s really interesting, and I think the idea of midlife wisdom schools are going to pop up especially given that we live in a higher education world; colleges and universities were in a lot of trouble before the pandemic.

Clayton Christensen, the disruptive innovation theorist, said years ago that by the year 2030, half of the colleges and universities in the United States will be gone. Wouldn’t it be interesting if we repackaged and rethought these beautiful campuses and turned them into places where people in midlife came back, did a sabbatical, did a gap year, and actually repackaged and repurposed themselves?

Why is learning exclusively something that the young do, and why isn’t wisdom something we cultivate and harvest over a lifetime?

Peter: That sounds like an incredible idea! I detect the seeds of a possible venture there, Chip!

Chip: I, you know, we are talking to a bunch of universities, and they’re in a state of trauma, to be honest with you. Because they were having this problem pre-pandemic, and now post-pandemic, if you’re a private university that has really charged a lot of money for something that people now feel like they’re doing online, how do you charge that premium? How do you start finding new customers?

Peter: It’s like a sort of reimagined MBA for, you know, anytime in life.

Chip: Yeah, can we thank everyone at MEA?

Peter: Yes!

Chip: Modern Elder Academy!

Peter: Talk to me about the idea of a midlife calling.

Chip: So the thing that’s interesting is that as Carl Jung, the psychologist, studied this, but also James Hillman and a few other people—the first half of your life, the primary operating system is your ego. In fact, the ego is almost the bookends of the ego are adolescence and middle essence. It’s not to say the ego didn’t exist pre-adolescence; it does, but it really comes into full ferociousness around adolescence.

Then around middle essence, you’re maybe late 40s, early 50s, you start to shift out of that. Most people don’t have any language for this. You shift into this primary operating system being your soul and you go a little deeper.

What happens is this weird thing happens where you start to actually listen to things you didn’t have time for because, frankly, your 30s and 40s are the rush hour of life. It’s the time when you have just the pile-up of way too many things happening at once.

It is in that period of time—starting often in your early 50s—where the curve of happiness starts to go up. People start to get in touch with the things that matter to them and the things they’ve always wanted to do but haven’t done yet.

Whether that is going back and from being a lawyer to going into being a schoolteacher or starting in a non-profit, or it means going out and traveling around the world for a year, becoming a digital nomad—which we think of as just a millennial thing—but I have a bunch of boomer friends who are digital nomads right now and are going around the world. They’re stuck in certain places right now, but they’re going to reopen and start traveling again.

So the calling is the idea that there’s a call, you know, to have a calling. There’s something calling you, and that doesn’t suggest it has to be a religious calling, although that’s the history of the word. It actually can come from something that’s just inside your intuition that says this is what I’m supposed to be doing now.

You know, midlife is the period of time when we basically throw off all of the uniforms that have been thrust upon us by other people, and we end up back in our bathing suit or birthday suit at a time in our life when we say, “Okay, I am going to focus on what matters to me.”

I’m curious how much we hold onto our age and the cycle of life that we’re in and how much agency we have to, you know, pursue calling, you know, earlier in life if that is sort of where we’re drawn?

Chip: Listen, I’ve had many colleagues early in life, so it doesn’t mean you can’t have a calling if you have it early in life—you absolutely can! It doesn’t mean that instead of feeling stuck in midlife or narrowing the opportunities, you have a smaller sandbox.

We start opening up possibilities that people aren’t used to doing in their 50s, 60s, and 70s. So, I absolutely think agency is a fundamental part of this that makes it work. The problem is, to go back to Carl Jung again, is often it is our shadows or our unconsciousness that actually lead us to our darkness. It’s the things that we’re asking about—the things that we’re not focusing on that are the blind spots.

So yes, if you’re the person who actually doesn’t realize that they have aged themselves and they are pouring Botox in their face to try to look younger because they’re worried about their job, that person is absolutely creating havoc for the rest of their life.

Because you can only do that for so long without looking stupid.

Peter: Do you describe that person as ageist?

Chip: Oh, I will. You know, ageism for a second—ageism, I mean, are you suggesting that ages are— you see somebody who’s trying to defy growing older as ageist themselves as if they are somehow part of the problem?

Chip: Well, when someone believes the following myth—that their best years are behind them— it may be true. Just when you’ve gotten comfortable in your skin, it’s started to sag. So it may be true that certain parts of our life get worse with time—physical health does.

Memory is not as good; you’re not as quick. But what a lot of people don’t know about is crystallized intelligence and the fact that your brain actually gets better with time up until your early to mid-60s in terms of being able to think holistically, synthetically, and connect the dots.

This is part of the reason why Brian liked me as the head of strategy in the company, because he could see that my mind thought holistically. Your heart and your soul get better with age.

What I see as ageism is when someone is assuming that life is purely all about having a midlife crisis and on the other side of that, you know, disease and decrepitude and a serious decline to death when, in fact, for those who don’t know, the curve of happiness shows that people get happier in their 50s than in their 40s, happier in their 60s than their 50s, and happier in their 70s than their 60s, with women happier in their 80s than their 70s.

So it is a U-curve that goes down from your early 20s to 45 to 50 and then goes back up. That’s life satisfaction, so I’m not going to point someone out and say, you know. “You’re an ageist.” Instead, I’m going to serve a book that doesn’t say, “Hey, how could we shift your mindset on that?”

That’s really the point here: We live in an era where we have a longevity revolution, and yet we don’t have a revolution in terms of our mindset around the thinking of age.

Peter: So that would be aging aspirational again. I mean, that’s the part of your work that is so resonant with me: the constant reminder that the institutions and the culture are not in step with the lifestyle and the biotechnology that’s keeping us alive so long.

We just have to rewrite some of these scripts or face real detriment. I think a lot of us feel it, particularly in the pandemic. I think now is, you know, more than any time, it is the right time to embrace some of these growth-oriented ways of being.

The idea that older people themselves can perpetuate this by thinking that it’s not possible and actually be contributing to the problem—I think is really insightful because that there—you know, I only think of ageism as going in one direction, from young to the old, not being sort of self-inflicted ageism.

Chip: Can it? You know, it’s actually a lot of studies have shown that sometimes the most ageist people are the oldest. But let’s also recognize that ageism can happen in the opposite direction too. If you’re in an old line company, financial services firm, manufacturing company, healthcare company, often the ageism is against younger people.

I happen to be in a tech company, so the ageism was potentially in the opposite direction. But ageism can happen in both directions.

Peter: Well, with that, we’re going to segue into audience questions. The first of which is: Chip, how old are you, and how do you feel about your age?

Chip: I will be curious—I am 59 and a half, so I’m turning 60 on Halloween! I am. Yeah, my 50s have been my favorite decade, hands down! No doubt about it; my favorite decade.

Peter: And why is that? Why has it been a great decade for you?

Chip: It’s been a great decade partly because I stopped caring so much about what other people thought about me. That was a huge, huge way, so that was in terms of that great midlife edit.

What no longer serves me is caring so much about what other people think of me. It didn’t mean I couldn’t be a caring and nice person; it just meant that it's compelling, you know?

Peter: Another question from the audience: How do you help midlife people move out of the desire of being forever young? I think this sort of goes back to the ageism, the fetishization of youthfulness. How do people break out of that?

Chip: You know, I think the most important piece of that is who you’re surrounding yourself with. It doesn’t mean you shouldn’t surround yourself with young people. I spend a ton of time with young people, and I was twice the average age of people in the company and had so many friends there.

What it means is who are the people you surround yourself with that are similar age to you, and what’s their point of view around aging? If you’re surrounded by people who are freaked out about it or having lots of cosmetic surgery or are lying about their age on Match.com or whatever they’re doing, or they’re narrowing their prospects of how they’re living their life because they’re living a fixed mindset, then you’re hanging out with the wrong people.

This is why I would say look at—and the last thing I would just say beyond just looking at books like my book or others—we have 400 books in our MEA library here. They’re all based upon how do you help people understand the unexpected pleasures of aging and what are some of the positives that come from it?

So there are lots of books out there on the subject, but I would just say stop seeing your body, your face, and your physical condition as the exclusive definition of how ripe you are in your life. Because if you do that, you’ll be a rotten banana pretty quickly! But if your heart and your soul and your intuition and your EQ—your emotional intelligence—grow with age, and your brain in terms of that connection, the dots and your ability to get out of your own way and your own ego, those are all things that get better with age.

Peter: Moving on to our next question. One viewer wants some book recommendations. Speaking of your library, what are a few books, Chip, or people that shaped your perspective on being a modern elder? What’s your essential reading list?

Chip: Sure! I’ll just throw out a few. “The Hundred-Year Life” by Andrew Scott and Lynda Gratton from London School of Business is a great book about a whole different perspective. They’ve been able to show that the average child being born today is going to live to a hundred. How does that change your society?

So, it’s a great book, but it’s particularly great for those of us in midlife, realizing that somehow our game of life, remember the book “The Game of Life” you used to play as a kid? It had one linear direction in it. Well, that doesn’t make any sense anymore!

So, it’s a great book. Mark Friedman has written a bunch of books on this subject. His most recent one is called “How to Live Forever.” It is not a book about how to become a robot. It’s truly about intergenerational collaboration and how to provide generativity and give back. That’s a great book!

There’s a book that’s coming out next month that I think will be very successful—I got the free reader copy. It’s going to be called “Transitions.” I don’t remember it, so I’m going to give you a different one instead.

I would say William Bridges’ book called “Transitions” is one of the best books ever written about how to go through transitions, and he has a book that’s called “The Way of Transition.” It’s also quite good!

Let’s come up with some women! I love anything that Margaret Mead and Gregory Bateson’s daughter has written. Her name is Mary Catherine Bateson, and she wrote a book called “Composing a Life.” It’s really very beautiful about how do you curate and compose a life and how do you do that, especially in midlife and later.

She has a great metaphor in that book about the midlife atrium. She says most of us have a tendency to think if we’ve got extra years, it means we have extra years at the end of our life. But the truth is that how many years of disease or decrepitude we have hasn’t changed much. So, we mean what we have—we have longer midlife.

The midlife atrium is when in midlife you actually have more years during the period of time when you have your physical health is usually pretty good, your mental health is good, and you still can make a big difference in your life.

So, how thoughtful! Architect and create the blueprint for your midlife.

Peter: Hm, that’s interesting! Again, another example of sort of the mist mapping and mischaracterization, you know, where we have this, you know, basically inflating idea of what old age is and, you know, everything that’s associated with it and what’s not possible versus, you know, a more authentic growth-driven re-considering, and I love that!

Moving on because we just have a couple of minutes left, and I want to make sure we get to as many of these as we can. One viewer wants you to summarize the skills that you think people need to be focused on in midlife and beyond. Are there specific skills that they need to train to be better at this and to harness, you know, these and other wisdom?

Chip: I would highly recommend people read Arthur Brooks’ article from the Atlantic last June, called “Your Professional Decline is Coming Much Sooner Than You Expect.”

While it’s a pretty depressing article for the first two-thirds of it because it talks about how our decline in a digital society is happening faster, the last third of the article is really interesting. It says the following: that we get better with aging at being less selfish, more synthetic in our thinking, better teachers, mentors, better coaches, better professors, better at being able to lead teams—we’re better collaborators!

One of the things that’s interesting is Google proved with their project Aristotle that the number one variable for successful teams at Google was psychological safety. One of the things that didn’t get nearly as much attention was that one of the elements of psychological safety is to have age diversity on teams, and generally speaking, when you have older people on teams, if it’s a very younger company, the older people on teams are really good at helping to foster collaboration.

So what that means is there are a lot of ways you can actually use instead of becoming a soft skill software developer in your 50s, you can become a soft skills developer in your 50s. Because you actually spend a lifetime developing those soft skills, and now is the time to leverage them.

Because frankly—I mean, one of the things I’ve said before is this: We see, you know, these young, digital brilliant people creating companies that make them billionaires in their 20s or 30s, but we expect these young digital leaders to somehow miraculously embody the emotional intelligence and leadership skills that those of us who are older have had decades to learn. So why not partner with them?

Peter: An opportunity as an employer, former CEO, and obviously, you know, top executive at Airbnb. How would you advise somebody in, you know, who’s in their middle-to-later life to present that set of skills? How do you go in and say, “Well, you know, I don’t know; I can’t code at all, but I can certainly, you know, anti-social developers better, you know, deliver product.”

How do you present that without coming across as presumptuous, I guess?

Chip: Let me say first of all, some software out there—the recruiting software is ageist in its algorithm, so that is one challenge people have. But if you can get to the place through your core contacts, or even your soft contacts, such that you can get an interview, here’s what you need to do: show up with curiosity and passionate engagement.

Because one of the best executive recruiters in the world told me this: “The best thing I can advise people who are say 45 or 50 years old and older is show up curious and passionately engaged.”

Because if you do that, what people will notice is not your wrinkles; they’ll notice your energy. And when they see your energy and sort of your sense of joy—let’s go back to your joy of life, your spirit, your zest, your sense of being someone who is in a constant state of evolution—then what you end up with is people not asking your age—not caring about it—because what they actually get is your energy.

Now that sounds sort of whoo! I don’t mean energy like, you know, okay? They see that you are energetic and passionate and curious. Generally speaking, in many cases, those are the qualities that a lot of people don’t think an older person has.

Now we just have time for one or two more. There’s one that I have to ask; it’s a bit of a flyer, but I am curious. This person wants to know: What are your thoughts on there being an upper age limit on the presidency? Should there be a point where we have a “best buy” or “sell by” date, basically? We have 35 to whatever right now; there’s no upper limit.

Chip: I think it’s the American people who decide that. I will say that Peter Drucker wrote two-thirds of the 40 books he wrote after the age of 65. He lived until age 95. Every two years, he would study a subject and become one of the Rosalie experts on it, and it had nothing to do with being a management theorist.

So I don’t think there should be an upper limit because I think that people have various skill sets, and their ability to be effective at whatever age. I do think that we need to be careful of people who are either fixed in their thinking and older, because that doesn’t do anybody any good, or potentially narcissistic and they’re older. Because if you haven’t actually outgrown your narcissism by your 70s, you probably never will be anything more than that.

Peter: Well, with that, Chip, I’m going to thank you. It was such a pleasure having you on Big Think Live.

Chip: Thank you, Peter! I appreciate what you guys do! It’s my second time, almost ten years later, so I appreciate coming back.

Peter: It’s so good to have you back! I have followed you for many years, and it is always a delight to see what you are up to because you are a true big thinker! So, thank you!

I want to thank the audience for joining us today. I want to also let you know that our next Big Think Live will be this coming Thursday at 1:00 p.m. with authors and spouses Michael Chabon and Ayelet Waldman.

Chip: Oh, I love them! I had dinner with them a few years ago!

Peter: Just, I mean, your rolodex, Chip! I feel like we’d save so much time and effort, but they will be discussing their latest book, “Fight of the Century: Writers Reflect on 100 Years of Landmark ACLU Cases,” and Maria Konnikova will be moderating, and she has a new book coming out as well called “The Biggest Bluff.”

So anyway, everyone, please join us if you can, and stay safe. Thanks again!

Chip: Bye!

Peter: Yeah, thank you, Chip! It was a pleasure!