Midlife And Beyond: Surfing The Liminal With Chip Conley

11 Oct , 2021 podcasts

Midlife And Beyond: Surfing The Liminal With Chip Conley

Midlife Crisis


Life is full of transitions, and the midlife crisis is simply a part of that. Chip Conley is the Founder of Modern Elder Academy. He is also a New York Times bestselling author whose manifesto on ageism, Wisdom@Work: The Making of a Modern Elder, is inspired by his experience of being both a mentor and an intern in his 50s. Entering the middle of his life, Chip realized the value of continuous learning and decided to share this wisdom with others. Today, he joins host Katherine Twells to discuss the “middlesence” and the importance of looking forward to what comes after retirement—the mindset of retiring to something versus retiring from life. They also discuss the intergenerational dance and the value of diversity in wisdom in solving the problems we face today. Tune in for an insightful discussion on age and overcoming the midlife crisis!

Listen to the podcast here:

Midlife And Beyond: Surfing The Liminal With Chip Conley

The Making Of A Modern Elder

In this episode, I am speaking with the incredible Chip Conley, who will be sharing the wisdom he has so beautifully earned by living a life of both adventure and re-invention. There is still so much more of his story yet to be written. Chip is the iconic boutique hotelier who helped Airbnb’s founders turn their fast-growing tech startup into a global hospitality brand. He’s a New York Times bestselling author whose manifesto on age-ism, Wisdom @ Work: The Making of a Modern Elder, is inspired by his experience of being both a mentor and an intern in his 50s.

After selling the company, he started as a rebel entrepreneur at age 26. Chip wasn’t sure what was next. He could have retired at age 52, but the young founders of Airbnb came calling. He served as Airbnb’s Head of Global Hospitality and Strategy for four years while also being CEO Brian Chesky’s mentor and continues as a strategic advisor to the company’s leadership.

While writing Wisdom @ Work, Chip was inspired to build the world’s first midlife wisdom school, The Modern Elder Academy, a three-acre oceanfront campus in Baja California, Mexico. Chip believes that curiosity is truly the elixir of life. He started learning Spanish and surfing at age 58. He is a true creator and a model for others to reframe how we think about our life phases and the power of intergenerational collaboration. There’s so much here to expand our perspectives. Please enjoy the conversation with the very wise and passionate Chip Conley.

Chip, thank you so much for taking the time to talk with me. I’m so grateful.

I’m honored to be here with you.

We got a chance to connect. It’s so fun when you feel this wonderful kindred spirit and someone like you, who has done so many extraordinary things and not done, which we’ll talk about. I’m excited to share more about you with our readers.

Thank you. I’m coming to you from Santa Fe, New Mexico. That’s where I am right now. It’s a gorgeous time of the year to be here.

The Chip Conley Origin Story

We’re going to be talking about the Modern Elder Academy in Baja, in Santa Fe. I’m like, “You know how to choose the geography.” It’s well played. Let’s start at the very beginning with your origin story. There’s the story behind the story, the real Chip Conley from the early years. What could you share about your origin story and then, more specifically, how it shaped you?

I grew up in Southern California. I was called the curious white boy in junior high school because I went to a predominantly non-white school. It’s an inner-city public school. Snoop Dog went to my high school ten years after me. I was culturally curious from a young age because I was not in the dominant paradigm as a white guy. I went to Stanford. It was very competitive to get in there. I played water polo there.

Midlife Crisis

Midlife Crisis: As a society, we are very fixated on accumulating knowledge. What we really need is wisdom.


I knew that I wanted to be an entrepreneur when I grew up. I went to Stanford Business School. A couple of years out of Stanford Business School, I started a boutique hotel company. This is the mid-1980s. No one had ever heard of them. Ian Schrager and Bill Kimpton were the two first people. I was the next. I called my company, Joie De Vivre, which means the joy of life in French.

Over the next 24 years, I ran that company as CEO. It became the second-largest boutique hotel in the US. I’ve created 52 boutique hotels. I sold it in 2010. The brand is now owned by Hyatt. A couple of years later, I was asked by the three founders of Airbnb when they had a tiny little tech startup to come to help them steer their rocket ship and democratize hospitality.

For years now, I’ve been helping them for years full-time and then the rest as an advisor. That leads me to where I am now. At Airbnb, they used to call me “The Modern Elder.” I wasn’t sure I liked that at first, but they said, “Chip, you’re as curious as you are wise.” I liked that. I ended up creating something called The Modern Elder Academy while I was writing a book called Wisdom @ Work: The Making of a Modern Elder.

It’s an extraordinary journey. Let me ask you this. We all have our paths. When I grew up, my mental model was I’m going to college and then I’d get a job. I go work for a company. Maybe this was my wiring. I never thought about doing my own thing. Now, much more so with the internet, people can do things, but back in the ‘80s, when we were coming out of school, it wasn’t necessarily. What do you think it was about your DNA, about you that said, “I want to be an entrepreneur?” What was that?

I felt it before I even went up to Northern California for college. Definitely, being in the Bay Area, you’ll get an entrepreneurial bug biting you. I liked the freedom and the creativity of it. When I was a kid, I had my own little restaurant in my parent’s dining room. It lasted less than four days. I had a neighborhood newspaper that I created and delivered to everybody’s homes. There’s a part of me that wanted to try new things and be a bit of a pioneer. That’s still is true now.

You’re a creator.

I am a creator. I’m also someone who’s called a social alchemist. It’s someone who’s a mixologist of people. I love that. I’ve been good at that since high school. I was the rush and social chairman of my fraternity in college. I’ve done that my whole life is to create a community in a variety of different forms. It’s not surprising that I would become a boutique hotelier, a restauranteur, and then ultimately Airbnb and now creating these cohorts in this community around the world of modern elders.

It’s not a matter of if I’m coming to Modern Elder Academy, it’s when. It’s the timing of all that because I’m so excited about that.

The door is wide open for you.

I cannot wait. There was a famous graduation speech by Steve Jobs. One of the things that he had said is you can only connect the dots looking backward. He talks about how he took calligraphy and how that fed into the creation of the Macintosh and all the different designs. As I listened to your story and you look back at you as that social alchemist and the four-day restaurant as a kid. You look back and you’re like, “The dots connect so beautifully.” It’s the essence of who you are.

Wisdom is not taught, it’s shared. Click To Tweet

The dots would sometimes even be connected moving forward. Within a few hours of joining Airbnb and being in their headquarters, I said to myself, “Same seed, different soil.” The same seed was me, hospitality and travel, but the different soil was a tech company. I could foresee moving forward, how do we take this little tech startup and turn it into a hospitality brand? I would say what’s been consistent throughout my career has been being a bit of a rebel and trying things and sometimes failing, but willing to have that noble experiment. I don’t call it a failure. I call it a noble experiment as a way of helping me cultivate and harvest my wisdom.

Here I am running a midlife wisdom school. It’s not surprising to me that along the way, there have been these little breadcrumbs that have helped me to find the path that I’m on. I think the hardest part for lots of us is safety, security, the worry of not succeeding, etc. These are the things that tend to hold us up. We’re in a part of our life where we don’t have the time to invest in being an entrepreneur. I get it. I think there are more and more entrepreneurs. The people who are in companies like Coca-Cola were saying, “What could we do in this company to try a new venture that if you were an entrepreneur, you might try it, but you can try it within an organization.”

I see it all the time. It’s like being on the trapeze, but the net is there if you fall. There are also a lot of resources and amazing people. I think companies are becoming more and more creative in their ability to let people incubate new ideas and bring them forward. That’s how companies are going to innovate truly is knowing ideas are going to come from everywhere. I agree. There’s room for everybody, all those curiosity seekers, whether you’re in a structure or outside of a structure.

The Challenges And A Mystical Experience

Before we dig into the wisdom school, I want to stay on your journey a little bit because everything shapes us in profound ways. Our journey has things that sometimes it’s fun and exciting. Other times, it’s hard. If you don’t mind me getting a little bit more personal, I know you’ve had some significant challenges with your health. When those things come up, talk about existential crisis, purpose and meaning. Can you share how those plot twists change things for you?

I’ll give you two plot twists. One in which I died. That plot twist was when I was 47 years old. It was the summer of 2008. I had a broken ankle, a septic leg and I was on crutches. It turns out that I needed to be on antibiotics. The first set of antibiotics didn’t work that much or not enough. They put me in a stronger one. I ended up having an allergic reaction to that, which happened while I was on stage at the end of a speech. Fortunately, I was sitting down at the time, signing books. I basically went flat line, lost any heartbeat nine different times over 90 minutes. That was 22 years into me running Joie De Vivre, the company I started.

I already knew in my heart that I needed to move on. What’s true for so many of us, we feel stuck because we feel like whether it’s safety or security or there’s an element of my identity. My identity is defined by this. I started a company when I was 26. It became very successful. This is my identity to the world. If I were to give it up, that’d be hard. This is the great recession. My company wasn’t worth anywhere near what it was two years earlier. This is stupid to do this now, but the divine intervention of that flat line experience helped me to have the chutzpah and the courage to say, “I’ve got to move on from this.” That was one experience.

The second experience was a few years ago. It was the day after my book came out, the day before my TED Talk and six weeks before the Modern Elder Academy was opening to the public. I found out I had intermediate-stage prostate cancer. This time, I wasn’t ready to throw in the towel. I’m starting something that I feel passionately about, but what it did is I trimmed my sails, so to speak. I curbed how fast we were going to grow for the next year to see how this was going to play out. It’s played out fine. I have my prostate taken out.

It’s a few years later. For a few years, I held out and had dormant cancer, but now it may be time to have it out finally, which we don’t need to get into that. I’m in a place where it’s like, “This is a time in my life where it’s time to shed things.” I do think that one of the things that are fascinating is if you’re going to live life, especially the midlife in people’s lives used to be 45 to 65, according to sociologists. Now it’s 35 to 75. This is midlife, a very long era, 40 years long. It’s a midlife marathon.

If you’re carrying baggage with you or a prostate that’s not working so well or identities or mindsets or habits that aren’t serving you anymore, people in your life who were fine twenty years ago, they’re not right for you now. Learning how to do what we call at MEA, the Great Midlife Edit is an important skill to build in midlife and beyond. Otherwise, you’re carrying all that baggage with you and you get worn out.

You certainly do. These are wise words. We are going to be talking about wisdom. Chip, for some people it’s like, “I got fired and that’s how I got pushed out of a job.” You had to die several times over. I’m curious on a side road and we’ll come back into this beautiful thing you’re creating. I have to ask this as you had that experience. Did you have a mystical experience?

Midlife Crisis

Wisdom@Work: The Making of a Modern Elder

I did. Mystical in the sense that I observed. I went flat line nine times and 3 or 4 of the times, the same nurse was with me and she was holding my hand. Each time I came back, and it said, “This is what I saw.” She says, “That’s what you said last time.” I saw the same thing over and over again, which was being in a mountain chalet with light coming through a skylight in the roof. It’s a beautiful blue sky. You can hear the birds chirping outside.

We’re on the second floor of this chalet, but no one’s there. It’s me on the second floor of the chalet. I’m halfway up in the air observing. What I see is the light coming in and creating a kaleidoscope of colors on the wall. The thing that was most noticeable was there was a very beautiful dark wood floor. There was this thick viscous oil frangipani-scented. It was tropically-scented. It was moving across the floor. It didn’t make sense based on location but I like the tropics, so that was part of it.

It was moving across the floor very slowly, going toward the staircase to the first floor. I was on the second floor. It was moving so slowly. What I took from this having this over and over again, was number one, is the beauty of life to seeing the colors, the sensuality, the smell. I was putting my hand into the oil to touch it. The beauty and the aesthetics of life often get lost when you’re so in your head. Secondly, slowing down because this was like all in slow motion. I think in many ways, I felt safe because if I’m dying, I’m dying a slow death. I didn’t feel like it was all speeding up. That was one of the messages I took from it. I was like, “How do I slow down a little bit?”

First of all, thank you for sharing that. It’s quite beautiful. I know whenever I’ve talked to other people who’ve had such experiences, whether it’s color or scents or light, there’s so much beauty. It’s an important reminder to us about beauty because so often we don’t see it or we choose not to or maybe we focus on the not so beautiful.

We do that a lot these days, don’t we?

Wisdom Journal

Especially right now, there’s a need for all of us to turn up the light a little bit brighter for that. Let’s talk more about how you’re doing that. Before we get into Modern Elder Academy, when I first learned about you, I was watching some of your videos and talks. As we at Coca-Cola started working with Wisdom Labs and launched the Compassion Lab at Coca-Cola, one of the first sessions I did was your session on editing and talking to people about that. I remember years ago learning about the wisdom journal that you keep. It’s a treasure that has been for your whole journey. Can you talk about that?

At age 28, I took a traditional journal that you might get to be given by a friend to write in and it had nothing in it. I wrote on the cover, “My Wisdom Journal.” I originally wrote My Dream Journal. I crossed out dreams to My Wisdom Journal. At age 28, I created a practice that I still do now, which is, every weekend, I try to metabolize in my mind and my heart what I learned that week. Not in the form of like, “Here’s how it felt,” but more like bullet points. If it was a normal journal, you’d have a lot more emotional expression. In this case, it was more like, “I want to understand. I want to try to digest some of my key lessons of the week.”

It was a weird thing to do. The reason I did it was because quite frankly, it was two years into having this hotel company and I was a bit overwhelmed. I’m feeling a little bit lost and I didn’t have a mentor who could help me. I tried to mentor myself by trying to make sense of what I’d learned. In essence, try to accelerate my wisdom and that’s exactly what it did. Nine wisdom books later, I don’t do it every weekend.

At this point, I do it about once a month, but for the longest time, for many years, I did it virtually every weekend. As a society, we are very fixated on accumulating knowledge, but you accumulate. All of that knowledge is in your little iPhone, but the truth is there is no knowledge. What we need is wisdom and wisdom is not all in your iPhone, it’s based upon your personal experience. Maybe what you’ve learned from others who have gone through a difficult time.

One of the things we say at MEA, the Modern Elder Academy, is that wisdom is not taught, it’s shared. The question is, how do you create the crucible for that wisdom to be shared? In the case of my Wisdom book, it was me sharing with myself. There have been times when I’ve gone back to my Wisdom books when I’m going through a similar time, and I was like, “What did I learn a few years ago when this happened?” I’ll go back and I’ll look at my notes.

If you’re going to live to 90, at 54 you have as many adult years ahead of you as you have behind you. Click To Tweet

It’s in my heart and my intuition. It’s probably in my mind, but sometimes going back and looking at what are the things I was learning back then helps me to say, “I have some pattern recognition. I recognize the pattern here.” Pattern recognition is a form of wisdom. When you can recognize a human pattern in yourself or others, you have unlocked your capacity to experience wisdom.

I think this is such a brilliant practice. That whole idea of metabolizing, to use your word, I’ll get this wrong, but there was some quote about the amount of knowledge we get in a day. Like Shakespeare, it was his entire life. There was some stat about the data coming in. There’s the neuroscience of how much our brain can hold. I can think about times I’ll be in a conversation with someone. I’ll be like, “I don’t know. I read somewhere from something.” I’ll pull something out of my mental computer that I accumulated from all this input. I don’t even know where I read this.

Your distinction about wisdom is so powerful because we can pare back all kinds of things we’ve read or studies or statistics, but wisdom is like letting it simmer, alchemize and reveal. Wisdom is revealing and you mentioned the patterns of something that maybe you didn’t see until you allowed it to go through, the oil dripping down the stairs in a very slow, beautiful way that reveals something. Like gratitude practices, it focuses your energy and your mind on this ability to learn and grow from this side.

Modern Elder Academy

I love that practice. Thank you for sharing it with everyone. Hopefully, some people out there we’ll give it a shot and see how it affects them. Let’s talk about the Modern Elder Academy and the birth of that. Maybe some of the transformations you’ve seen because speaking from someone who’s in midlife, now that you’ve expanded many years, I don’t have to reveal too much about my age. I am maybe approaching modern eldership. Share a little bit about the journey on that.

The sprouts started during my time at Airbnb. I joined the company at age 52. The average age in the company was 26. I was an elder. It’s a relative term. I was an elder, but one of the things I started to get curious about while I was there, full-time, was, “Why don’t we have better intergenerational collaboration? Why don’t we connect across generations better, both in the workplace and outside of the workplace?”

When I finished my full-time work, I went down to Baja, where I had a home on the beach, and I said, “I’m going to write my fifth book.” The fifth book was called Wisdom @ Work: The Making of a Modern Elder. While I was writing that book, I had this Baja a-ha. I had an epiphany on a run on the beach. I said, “Why is it that we have no midlife wisdom schools? Why don’t we have a place where people can in a group do what I was doing in my wisdom book, which is to try to make sense of what they’ve learned along the way and share that wisdom with others?” As well as how to repurpose themselves and even reframe their idea of aging.

We have a very toxic relationship with aging in American culture and mostly global culture now. It’s almost true everywhere. The culture is basically, “If you can survive your midlife crisis, on the other side of that, you have this disease into decrepitude and you die.” The truth is if you’re 54 years old and you’re going to live until 90 and the chances are moderately good that if you get to 54, you’re going to live to 90. That’s the average age of the people who come to MEA is 54.

Demographics are quite different there in terms of longevity. If you’re going to live to 90 and you’re 54, you have as many adult years ahead of you, 36 as you have behind you, 54 minus 36 is 18, 54 plus 36 is 90. At age 54, I’m only halfway through my adult life. That math equation freaks people out because it says, “I need to go learn a new language. I have another career in me. I don’t want to spend the rest of my life golfing. I don’t want to spend the rest of my life crocheting,” or watching TV. The average retiree in the United States watches 47 hours of TV a week.

Retirement, which you think would add life, does the opposite. The average person who retires increases the year of their mortality by two years. Part of the reason that we lose some of our health in retirement is, number one, we have less of a sense of purpose. Number two, we have less of a sense of wellness. The discipline of knowing you’re going to the office creates a regimen and that structure allows you to say, “I go to the gym 3 or 4 days a week. I go swim,” or whatever it is.

The community piece is we lose our sense of community often because so much of our sense of connection socially revolves around work. Purpose, wellness and community come from a doctor named Dr. Phil Pizzo from the Stanford Medical Center. Long story short is that’s what we do. We focus on helping people with their purpose, wellness and community.

Midlife Crisis: When you have a growth mindset, you focus on improving yourself, not proving yourself. You focus on success as defined not by winning, but by learning.


I have to tell you, Chip, certainly, being in that camp, it’s such a noble and needed thing. It’s so needed. I have to imagine it will have a huge impact on the trajectory of people who come to that stage without knowing where to go and can be reframed in the community. I think about this whole pandemic time. The pulling apart of people and community certainly has affected our mental health and wellbeing in a significant way. Being able to come back together, heal, explore and create is such a powerful thing. You learn to surf at that point.

I’m not very good yet. There’s a woman named Carol Dweck from Stanford. She’s a psychologist. We love her work. She talks about fixed and growth mindsets. When you have a fixed mindset, you tend to be focusing on improving yourself. You define success as winning. When you have a growth mindset, you focus on improving yourself, not proving yourself.

Success is defined not by winning but by learning. Getting to a place in midlife or later, where you can have a point of view that you want to learn something new and you don’t mind looking a little silly learning something new, it’s a pretty important trait to learn in life. If you have a fixed mindset, you only will play the games that you can win.

The Growth And Happiness Mindset On Age

Over time, your sandbox gets smaller and smaller because there are certain things you don’t do as well as you get older, but there are other things you might do better. Just like curiosity has been seen as the elixir of life, curious people live longer. Openness to new experiences is also considered an elixir in life. People who tend to have an openness to new experiences live longer.

The last thought is the study that came out of Yale from Becca Levy has gotten a lot of attention, which shows that if you can shift your mindset from neutral or negative about aging to positive, you add 7.4 years to your life, all of the things being equal. That’s more longevity added than if you quit smoking in mid-life or started exercising. From a public health perspective, helping people to feel better about their aging and helping society be less ageist would be exceptional for helping people to not live longer lives but also live happier lives too.

The research is so powerful and it’s so much about our frame. If we talk about your Wisdom book and cultivating, focusing on wisdom, where your focus is where your energy starts to go and what we’ve learned about neuroplasticity and certainly at Coke, growth mindset has been a big part of our internal cultural voices. How do we continue to be in a learning culture?

Did you do it right or wrong and achievement all the time? It’s such a powerful frame to shift into this level of open possibility. I think we’ll keep learning more and more. It’s open happiness. I get excited about what we’re going to keep learning about what type of lives we can lead. As a matter of fact, isn’t there a research that when they measure happiness, people are happier as they get older?

It’s called the U-curve of happiness. It’s a fascinating series of studies that have been done across all cultures that show that you bottom out on your adult happiness around age 47, which is when I had my flatline experience. With each passing decade after that, you get happier and happier. Happier in the 50s than in the 40s, 60s happier than 50s, 70s happier than 60s. It is a fascinating thing. There are a lot of reasons for it. Some of it is you get comfortable in your skin when it starts to sag.

You would never know that was the case based on the cultural voices we hear.

The cultural voices say it gets worse. Let’s say your mileage may vary here. The bottom line is not everybody has this experience, but what’s fascinating is how much you can control that perspective, mindset around aging and what health results that lead to.

If you can shift your mindset about aging from neutral or negative to positive, you add 7.4 years to your life. Click To Tweet

You have that group of friends. You’ve been traveling on the journey together for a long time. You all go out and everyone starts talking about their ailments. It’s like, “No. We’re not going into a whole dinner about what’s going wrong.”

I call that organ recitals. “No organ recitals here. We don’t need to hear about all your organs.”


Diversity In Wisdom And Wisdom In Diversity: The Intergenerational Dance

Here’s a question as we’re talking about knowledge and wisdom. You are probably the master based on your experience, having worked with Airbnb and being in the 54 to 25 ratio. It was interesting. Several years ago, when the Millennial conversations were so big, we started this group called Millennial Voices. Like, “Let’s hear from this younger generation and make sure we understand.”

We’ve gone through reorgs. All of a sudden, “We’re losing all this tribal knowledge. People have been around the company for 20, 30 years and knew our legacy and our history.” There’s this beautiful value of merging fresh thinking, knowledge, energy with wisdom and experience. Talk a little bit about that intergenerational dance and what opportunities are there?

I like to think of it as a generational potluck. In a potluck, everybody brings to the table what they do best. We all get to feast as a result. There’s some truth to that in terms of how do we solve vexing societal problems or within a company or even a team, how do you solve things differently? Let’s give a little bit of background again. I do like to go back to science because otherwise, it’s just my opinion.

Some of the science shows the following. Number one is the younger you are, the more focused your brain is. Your brain tends to gets focused, which is quite good in some ways. That’s not true. If you’re like six years old, you’re totally unfocused, but in your adult brain, being younger means, you’re more focused. You’re brilliant at technology typically. Not always, but generally, that’s true. You’re a digital native as opposed to a digital immigrant like me.

One of the challenges with focus is you don’t see peripheral vision. You don’t see around corners. You don’t think systemically or holistically because you’re so focused on the thing right in front of you. I saw this over and over again at Airbnb where I was on teams. I was like, “The team had a vexing problem they were trying to solve, but they didn’t realize the thing they’re trying to solve. There was a deeper problem that’s leading to that problem.”

If we can solve that deeper problem, it would solve not this problem but a bunch of other problems as well. That’s called systemic and holistic thinking. It’s something you get better at with age. Maybe it’s because of wisdom, seeing pattern recognition, your brain is less focused and you can move from left brain to right brain much more adeptly as you get older. That’s something that gets better.

Another thing that gets better is emotional moderation and intelligence. IQ does not improve with age, but it’s supposed to stay relatively static but EQ can improve with age. Why is this important? It makes for a better person to work with if you’ve got someone who’s mostly moderate. Where there’s some interesting research on this what the research that Google did with their Project Aristotle, where they studied the most effective teams in Google in the world and then tried to figure out what were the common variables. The number one common variable was psychological safety.

Psychological safety on a team means that everybody feels like their voice can be heard. They don’t feel too vulnerable if they’re a non-dominant voice. If you’re a woman in a group of six men, you feel like you have as much of an opportunity to speak. Psychological safety is improved when you have age diversity on a team. It’s partly because of the emotional moderation of the older person. It’s partly because that diversity adds additional flavors so that the group thinks that sometimes can happen is not allowed to happen as much as it would otherwise because that diversity allows the varied voice in the group.

Midlife Crisis

Midlife Crisis: Think of it as a generational potluck. Everybody brings to the table what they do best, and we all get to feast as a result.


It doesn’t have to be demographics. It can be a different way of introvert versus extrovert. That diversity sometimes helps you to see things that you wouldn’t have seen on your own or if you’re surrounded by people who are like you. Age diversity is as important as any other demographic, but most companies haven’t figured that out yet.

I would say in many companies, people start to feel when they cross that line of 50 that it’s time to let the new people run the show. I think what you’re saying is there have been so much deep and emotional conversations in 2020 about diversity and our evolving consciousness about what we all are bringing into this. Diversity of experiences, frame, age and gender, and all of those things are powerful. I think these studies that Google did prove that out. This is the equation for your highest level of success. We need to be listening to how powerful that is as we come together.

It’s inevitable as we’re living longer. People are going to be staying in the workplace longer. The retirement age, which was going down and down around the year 2000, grew again. People are staying in the workplace longer. It’s a fascinating statistic that came out from the Federal Reserve that showed the following. There were 11.7 million new jobs created between the years 2000 and 2020. Those 11.7 million new jobs, went to people 60 and older.

Let me think abstractly. Basically, the whole growth in the labor force between 2000 and 2020 was people 60 and older. Just so everybody doesn’t like, “What the hell are you talking about, Chip?” No, it doesn’t mean that only older people got the jobs. No. It means that the number of people who are 60 and older in the workforce increase that much partly because Baby Boomers are a big generation and people are staying in their jobs longer. Why is that relevant? I was like, “This shows that the workforce is getting older.” The solution here is not to say, “Let’s put everybody out to pasture at age 62,” but it’s more to say, “How can we tap into that 63-year-old who does not want to leave here until they’re 75?”

This is going to age me because half the people reading won’t probably understand where I’m getting this term. The way we live our lives, you see it in people. It’s amazing.

In Silicon Valley, 30 is the new 50. What does that mean? It basically means that physically we’re getting better with age, but power is often moving to younger people, as was true in Airbnb. Airbnb now, a lot of people don’t know this, is the most valuable hospitality brand in the world. The valuation on the stock market of Airbnb is worth Marriott, Hilton, Hyatt, Four Seasons and Intercontinental combined. That’s nuts, but that’s true. This is not like a little blip. Airbnb has been a public company now. It’s enough time for people to say, “Okay.” That’s a company that gets started by some 26 and 24-year-olds who had no background at all in travel.

When I’m talking to my fifteen-year-olds and talking about YouTube and I’m like, “You can’t. You need to go do this and get off that computer. There’s no career in there.” They’re like, “Mom, this YouTuber who’s nineteen is making $150,000.” I’m like, “How do I start a channel? Can you educate me on this?” We had to work our way up the ladder and the old model is amazing empowerment.

You were alluding to it. The three-stage model of life was based upon you learn until you’re 20 or 25. You earn until you’re 65 and then you retire until you die. That model, if you are a Baby Boomer or a Gen X-er, you grew up with that and it’s familiar. If you’re a Millennial or Gen Z, you have no idea what we’re talking about because they’re like, “What are you talking about?” I have to have that linear model. I might take a gap year at age 38 or I might go back to get a PhD at age 47 or I might choose to start a company in my mid-50s.

The idea is that there’s some linear path and I hate to say this Coca-Cola because Coca-Cola is one of those great companies that has had a lot of loyalty in their workforce. People sometimes stay with the company for a long time. It’s perfectly fine. In fact, when loyalty is a scarcer commodity, which I think is true in the workplace now, those who provide loyalty, those employees who offer loyalty have something that’s more valuable because scarcity creates value. I’m not suggesting people shouldn’t be loyal, but what I am suggesting is that the old model of like, “You have to be loyal.” You don’t have a choice. It is retiring.

The Forward Motion: Middlesence And The Retiring To…

Everything is being newly created as the landscape changes and the values change and each generation puts its fingerprint on it. It’s going to be fascinating to watch it. It’s great because there are so many new possibilities. One of the other things I wanted to ask you about before I’ll start to wrap it up is to be very mindful of your time, but I love something you said.

People spend all the time talking about retiring from, but what are they retiring to? Click To Tweet

I was watching one of your interviews. You talked about the difference between leaving something and going to something. I love that distinction because I can think of many conversations I’ve been in where someone’s like, “I’m done. I got to get out of here,” versus the excitement of, “I want to go to this.” Can you talk about that for a moment?

Sometimes I talked about it in the context of retiring or leaving a job. There’s a freedom of being able to say, “I’m done and I’m going to move on.” What often people do is they get so fixated on the “I’m done. I’m going to move on,” instead of focusing on where they were that they haven’t figured out where they’re going. This is particularly toxic in retirement because people know, “I want to get that freedom. I want to have that space,” but they’ve spent all the time talking about retiring from, but what are they retiring to?

What is it that is going to be the thing that’s going to make them passionate, give them a sense of purpose, etc.? When we are left in-between spaces where we feel somewhat lost, it’s what’s called liminality. A lot of people come to Modern Elder Academy is exactly that place, “I’m confused. I’m going to transition. I don’t know how to get to the other side.”

Unfortunately, it’s also a period of time when a lot of other things happen, too much drinking, death by despair or someone feels really lost in that period. Being able to make sure that you’re not retiring from something or leaving some job, but there’s something that you’re moving toward helps to create an organizing principle around how you’re spending your time.

To be in a mode of creator, there’s a forward motion. I think what you articulated is all too common. We talked earlier about sometimes we say too long, safety, security, but we get into groups. We’re creatures of habit. “This is the way I roll.” You start to feel that cognitive dissonance. You know change. You feel that pull. The change is there and there’s all this energy with, “I’m done,” versus the power of creating your next chapter, which I think that’s why Modern Elder is filling in such a wonderful service to take people by the hand and guide them through that process.

What’s so funny is that adolescents are very familiar with now. You have adolescents in the household. Adolescence as a word didn’t exist in 1903 until 1904, a word that got created. Prior to that point, if you hit adolescence, you were an adult, and that’s why you had got married and had kids. You worked in the coal mines or the mining factory or whatever. A psychologist came up with the word adolescence and said, “Adolescence is an in-between period between childhood and adulthood.”

You go through a lot of hormonal, emotional and identity changes during that time. There’s a new word is about twenty years old called middlescence. It’s an in-between stage between adulthood and elderhood. You’re elderly when you’re in the last 5 or 10 years of your life. At age 52, I joined Airbnb. I was absolutely an elder there. You can be an elder, relatively speaking, at many ages. The in-between period of middlescence is also a period like adolescence, where it’s a little awkward. You’re going through hormonal changes, menopause and andropause.

You’re going through identity and physical changes a lot. When adolescence was discovered in 1904, all of a sudden, the government put an enormous amount of money into public junior and senior high schools. Where are the prep schools for elderhood, for people in middlescence? Where are people 45 to 60 years old going to learn what it means to be at the stage in their life? That’s why we’re the world’s first midlife wisdom school.

I am excited to experience it. I’ve said this, but it bears repeating. I’m so happy you created it in the world and there’s so much transformation that’ll come from it. If people reading want to find out more about this and certainly the folks that are reading are going to be of all ages. I hope our younger readers are also taking from this conversation the power of wisdom and tapping into older mentors. Let’s say you’re at a place you want to go. There’s a website. Where would people go to get information about Modern Elder Academy?

We’ve had people as young as 30 and as old as 88 come to our workshops in Baja. You can go to ModernElderAcademy.com and you’ll learn about our three kinds of programs. Our Workshops In Baja and soon in Santa Fe, New Mexico. Our Sabbatical Sessions, which you come for an extended stay. You have a lighter amount of programming. A lot of people are digital nomads. They stay and live on the beach in Baja with us and are doing that. Our MEA Online Program, which is the most accessible program. It’s the most affordable. You do it from your home. It’s an eight-week program. You’re in a small cohort of eight people and you learn about transitions.

Midlife Crisis

Midlife Crisis: Making sure that you’re not just retiring from something or leaving some job, but there’s something that you’re moving towards, helps create an organizing principle around how you’re spending your time.


Thank you for sharing that. As we wrap things up, two last things I’d love you to share. One is, first of all, you’re an amazing writer, author. I think you said you didn’t count your first one, but like nine books that you’ve written from so many different angles and beautifully done. You’re a voracious reader, too, from watching Wisdom Well blog. There was one where you shared some of your favorite books. Other than the ones you’ve written, any favorites you would share with people?

I love Viktor Frankl’s Man’s Search for Meaning. It’s a famous book about what it was like as a psychologist to live through being a prisoner in a concentration camp in World War II. It sounds terrible. It is hard to read at times, but it’s absolutely an opportunity to connect with the fuel of meaning. There’s a new book that came out from the UK called Re-educated.

A woman named Lucy Kellaway, who was a financial journalist, decided to go back to teach in public junior high schools or high schools. It’s a beautiful book about how do you make a transition in your life. For those who are interested in the bigger study of what’s it going to be like if all of us on average are living to 100 years. There’s also a great UK book called The 100-Year Life. I’m a big fan of that one.

This conversation has been chock-full of wisdom from start to finish. It’s certainly not been lacking. In your incredible journey, all these experiences that you’ve had and all the wisdom books that you’ve written, is there one other piece of advice you would leave everyone with?

My last piece of advice would come from Jimi Hendrix, the famous musician, who said, “Knowledge speaks and wisdom listens.” A person who is wise is able to listen inside of themselves well, but you know when someone’s wise and they’re listening to you and you can feel their attention. There’s also listening for the field or what’s happening in the room or almost energetically. A person who’s wise is able to listen on all three of those levels inside, one-on-one and to the field at the same time. That is a talent, but it’s a talent that can be built. It’s one of the talents, the skills we teach at the Modern Elder Academy.

That is wonderful, Chip. That’s a practice. When you think about how we’re cultivating wisdom over time, being able to learn how to be present as we get more comfortable in our sagging skin or as we learn, there’s more to us than our egos and in our resumes. We start to tap into that space inside of what we are here for, how beautiful to move into that space of deep listening and creative power. That’s a brilliant way to end it.

Ending on a musical note, I didn’t bring enough song lyrics into the middle of this, but I always love beginning and ending with music. I want to thank you for being with me and for sharing so much with everyone who is reading this. I want to thank you for what you’re doing in the world and for being bold, an alchemist, a creator, and creating ripple effects for everyone that you touch. Thank you so much.

Thanks so much.

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About Chip Conley

Chip Conley is the iconic boutique hotelier who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand, He is a New York Times bestselling author whose manifesto on ageism, Wisdom@Work: The Making of a Modern Elder, is inspired by his experience of being both a mentor and an intern in his 50s. After selling the company he started as a rebel entrepreneur at age 26, Joie de Vivre Hospitality, Chip wasn’t sure what was next. He could have retired at age 52. But the young founders of Airbnb came calling. He served as Airbnb’s Head of Global Hospitality & Strategy for four years — while also being CEO Brian Chesky’s mentor — and continues today as a Strategic Advisor to the company’s leadership.

While writing Wisdom@Work, Chip was inspired to build the world’s first “midlife wisdom school,” the Modern Elder Academy, with a 3-acre oceanfront campus in Baja California, Mexico.

He believes curiosity is the elixir of life and started learning Spanish and surfing at age 58.

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