Live Long and Master Aging podcast



Wisdom, curiosity and the modern elder

Chip Conley: Founder, Modern Elder Academy

BY PETER BOWES | JANUARY 8, 2021 | 1430 PT

As we push the boundaries of human longevity and our expectations for lifespan, mid-life is going to be different.  Our healthy, vibrant decades are being extended. The goal of enjoying more fulfilling years, free of diseases and physical decline is becoming a reality. The trajectory of our lives is changing. 

Chip Conley is a veteran executive in the hospitality industry, formerly Head of Global Hospitality and Strategy with Airbnb and a prolific writer.  He’s also the founder of the Modern Elder Academy, a self-styled school for midlife wisdom and the author of Wisdom@Work: The Making of a Modern Elder.

In this conversation with Peter Bowes, Chip shares his vision of older people as wise, curious and indispensable members of society. He recalls the impact of a near-death experience, the way his life went through a transformation in his 50s and the art of lifelong learning.   

Recorded: December 29, 2020 | Read a transcript

Connect with Chip Conley: Personal website | Modern Elder Academy | Wisdom@Work: The Making of a Modern Elder | Facebook | Twitter | Instagram | LinkedIn

Photo credit: Lisa Keating

“My vision of my future is dedicated to curiosity. Curiosity is probably the most important elixir in life, maybe more important than the physical things you do.”

Chip Conley

Topics covered in this interview include:

  • Chip’s life-defining brush with death and experience of going to the “other side” during a medical  emergency. 
  • Doing business as a “hospitality disrupter,” as one of the first boutique hoteliers and later with Airbnb.
  • Creating the Modern Elder Academy (MEA), mid-life wisdom school.
  • What is long-life learning? 
  • The unexpected pleasures of aging.
  • Focussing on “great longevity” and a spiritual diet. 
  • Upgrading the human operating system – moving from reverence to relevance as a “modern elder.” 
  • Launching the MEA – a regenerative community – a 21st century version of a retirement community. 
  • Taking the less traveling path in life.  
  • Having regrets or no regrets in life?  
  • Metabolizing and cultivating wisdom from life’s experiences.
  • Acknowledging and challenging “new year resistances” fears and old habits.  
  • Role models for a living a very long life.  
  • Embracing curiosity as tool to live a long life. 
  • This episode is brought to you by AgeUp, a new product that helps fill in the financial gaps that are often created once you’ve mastered aging and achieved an exceptionally long life. Small monthly payments to AgeUp stack over time to create a secure income stream for your 90s and beyond. Contributions to AgeUp are shielded from market swings, and once payouts begin at age 91 or above, they’re guaranteed to last for life. AgeUp is backed by MassMutual and sold by Haven Life Insurance Agency. You can find out more at


Chip Conley: [00:00:00] You don’t have to be an older person like you and me, Peter, to actually go out and determine how are you going to accelerate your process of becoming wise. I started doing that at age 28, and I think anybody could do that at any point in their life.

Peter Bowes: [00:00:21] Hello and welcome to the Live Long and Master Aging podcast. I’m Peter Bowes. This is where we explore the science and stories behind human longevity. This episode is brought to you by AgeUp, a new financial product that provides guaranteed supplemental income for people who worry about the financial impact of longevity. To find out more, visit Age-Up dot com. That’s Age-Up dot com. Now, the ethos of this podcast, the big idea is focused around lifestyle interventions that help us live longer, healthier lives, extending our healthspan so that we’re more active, more involved, more alive as we grow older. For many of us, that concept is well within reach. But what we may not have thought so much about is how are we going to reposition ourselves or reinvent ourselves midlife to take advantage of those extra years that we’ve perhaps worked so hard to achieve. And by that, I mean society is so well accustomed to generations of people moving from childhood to adulthood through a working life, perhaps parenthood, and then suddenly, sometimes slowly but more often suddenly transitioning into retirement and a different pace of living. What if we’re not ready to accept those social norms? Well, my guest today has thought a lot about that. Chip Conley is the founder of the Modern Elder Academy, which, according to its website, is the world’s first school for midlife wisdom. Chip is a veteran executive in the hospitality industry, formerly head of Global Hospitality and strategy with Airbnb, and he is also a prolific author. Chip, welcome to the Live Long and Master Aging podcast.

Chip Conley: [00:02:00] And such a just an honor to be with you.

Peter Bowes: [00:02:03] And it’s a real honor to talk to you as well. You’ve had a fascinating life and career, and I perhaps understated maybe some of your achievements. You’re also something of a rebel, a disruptor

Chip Conley: [00:02:16] That’s true

Peter Bowes: [00:02:16] in the hospitality business. And before we delve into mid-life wisdom, maybe you could give me a snapshot of your career to date and what brought you to the place that you’re in now in terms of your working life.

Chip Conley: [00:02:26] Sure, at age 26, I decided to start a boutique hotel company based in San Francisco, California, and the boutique hotel movement was just getting off the ground in the mid 1980s. When I did that, it was called Joie de Vivre means joy of Life in French. And over the next 24 years, I was the CEO of that company. It grew into the second largest boutique hotel company in the United States. And we created 52 boutique hotels and then the Great Recession. I decided to sell it. I just was like I was over it. I was in mid-life. I was struggling with the low point of the curve of happiness. For those who know that, we’ll probably talk about it more later. And I needed to do something new, but I really wasn’t sure what I was going to do. And if you ever saw the film with Robert De Niro and Anne Hathaway, The iItern, you know that he says in the film, musicians don’t retire. They quit when there’s no more music left inside of them. I knew I had music inside of me. I just didn’t know where to share it. That’s about the time that the Airbnb founders approached me and said, Chip, we want to democratize hospitality. Will you help us? And then I spent the last eight years helping them for years, full time, for years then as an adviser. And it was during my time at Airbnb that I came to the conclusion that, well, first of all, they started calling me the modern elder, which I wasn’t sure if I liked or not. They said, Chip wou are as curious as you are wise, and that’s what a modern elder is. Well, OK, that sounds good. Better than modern elderly, I guess, but I don’t know. What I started to think about was how as a society have we helped prepare people from adulthood to elder hood because your elder years, meaning you’re sort of to me elder is a relative term. It means you’re older than the people around you, but it doesn’t mean you’re your elderly years, which might be less five or 10 years of your life. Your elders years might be as long as your adult adulthood years. And if that is true, then we are woefully ill prepared to help people to understand this era of their life. That’s what led me to write my book, Wisdom at Work The Making of a Modern Elder and then create the modern elder academy.

Peter Bowes: [00:04:31] Yeah, I think it’s fascinating the way that you frame it and the fact that it’s absolutely right that our elder years, those old years, those, as some people might traditionally see, those declining years,

Chip Conley: [00:04:42] Right.

Peter Bowes: [00:04:42] Are actually not going to be that anymore. They are going to be long years, long summers ahead of hopefully good health and active lifestyles that we need to prepare for in midlife. As you describe just before we as they go more into that, there is one of the lifetime experience that you have gone through that obviously made such a huge health wise that made

Chip Conley: [00:05:04] Hmm.

Peter Bowes: [00:05:04] A huge impact on you and your vision and I suspect your vision of yourself in your later years in your elder life.

Chip Conley: [00:05:12] Well, there’s been a couple, but the one I think maybe you’re talking about, the one at age 47 when I went flatline.

Peter Bowes: [00:05:16] That’s the one.

Chip Conley: [00:05:17] Yeah, in the midst of gosh, it was August 2008. I was going through terrible things in my life. I just just about everything that could go wrong was going wrong and the Great Recession was getting started, etc.. And I had a broken ankle and a bacterial infection in my leg. And I ended up having an allergic reaction to a very strong antibiotic. And I went flatline on stage after a speech. And that was when I really woke up. I was 47 years old and I woke up and said, listen, is this what I want to do? You know, I’ve been doing it at that point for 22 years. And and I just realized I had a curiosity for life that felt like it was being restrained by what I was doing. So to die and go to the other side and then come back and be retrieved based upon the paddles they put on my chest, I was able to get to a place where I said, listen, I’m going to take you every day a lot more seriously and more gravitas and levity. I think think one of the great things about later life is you learn the perfect alchemy of when when there’s gravitas needed and when is levity needed. And in that moment, I wanted both and I, you know, started the process of selling my company.

Peter Bowes: [00:06:33] You say you went to the other side, how aware of that were you?

Chip Conley: [00:06:38] So aware that each time I – I died nine times over the course of 90 minutes and when I say died, what I mean is my heart stopped and it went flatline. In certain cases, it restarted five or seven seconds later. In other cases, they had to actually use, you know, external electric means to just, you know, zap my heart. And so it was interesting. You know, I’m a healthy guy. People who are listening to this, they don’t necessarily know, you know what? I got to the emergency room. They said, ah, you are a marathon runner because they just thought I was, like, having a hard time. My heart rate is too low. And so long story short is the way I knew I went to the other side. It was each time I would wake up from that experience, I would say to the person next to me, this is just what I saw. And so each time I saw the same thing and so there was an element of go, wow, I had what is called a near-death experience NDE that I treasure. I really do treasure the idea that I have a much less fear around death, having experienced a short version of it,

Peter Bowes: [00:07:50] And what did you say? That’s the obvious question, people want to know. 

Chip Conley: [00:07:54] Take this could take the whole section.

Peter Bowes: [00:07:56] Give me the short version.

Chip Conley: [00:07:57] I’ll be brief. Short version is I was an Alpine chalet, a beautiful home. There’s a skylight in the home with the sun streaming in. There is an a wooden floor with heavy scented, beautifully tropically scented oil on the floor. The sunlight is casting a kaleidoscope, beautiful set of colors on the wall. And this oil is just going down these steps very slowly. And I’m an observer in the room. There’s nobody else in the room. There’s birds chirping. It’s just it was sort of a sensuous experience. Visually, I could smell the frangipanis scented tropical oil and the birds were like, you know, like a chorus. So what I took from that was that life moves slowly because the thing I was noticing was how slowly the oil was dripping down the stairs. And I think what I noticed is just like, wow, life can move more slowly than it has been moving for me and it can be more spacious. And so, you know, that was that was it. I mean, it was more it was beauty, the sense of beauty and the sense of stillness.

Peter Bowes: [00:09:17] Well, you’re right, we could probably spend the entire podcast analyzing that experience. And it is a fascinating one.  

Chip Conley: [00:09:21] You could be my therapist. 

Peter Bowes: [00:09:22] Yeah, well, you probably wouldn’t get very far on that, with my advice. But no, it is a fascinating area. But let’s delve into, let’s say, the impact that it had on you in the years following and your attitude towards life. And you were already midlife. You’re 47 years old, which is a young midlife in my mind. But

Chip Conley: [00:09:42] Yes,

Peter Bowes: [00:09:42] It must it must have changed your mindset.

Chip Conley: [00:09:45] It did. I mean, I think what I I came to the conclusion about on was the idea that now I have if I do the math and how much of my adult life I still have ahead of me, I only have twenty nine, twenty nine years of adulthood that I’ve racked up at that point. And if I’m going to live till 98, let’s say I have, 51 years, something like that. Yeah. 51 years ahead of me of adulthood. 51 years ahead of me. 29 year behind me. I’m maybe a little bit more than a third. Through my adult life, I had been thinking that my life was almost over. And, of course, you know, dying will do that to you as well. But I think more than anything, I actually felt the sense of handcuffs. I weirdly, in my backpack and my little briefcase backpack when all this happened was a book by Victor Frankl, Man’s Search for Meaning. And so I came to the conclusion that I was supposed to read that book the next two days in the hospital. And I did. And I’d read it before, but I acquainted myself to the idea of this man was in a concentration camp in World War Two. Well, I realized I was in my own version, you know, taking no gosh. I mean, the last thing I wanna do is to make light of anyone who has had family in the Holocaust. So I’m not making light of it. But I’m just saying I was in my own version of a concentration camp of my mind. I was a prisoner and I was a prisoner in ways that were completely I had so much more choice than I thought I had. So at the end of the day, I think the way it influenced me as it helped me to see I have a lot of life ahead of me. I don’t have to do the thing I’ve always been doing. The identity that has been sort of defining me doesn’t it can actually go away and I can create a new identity. And that identity was for 20, ultimately 24 years, being the founder and CEO of a very well-respected boutique hotel company. And as soon as I was going to sell it, that was I was now the past as the founder, but the former CEO, I was sort of living in the past then, and I didn’t want to live in the past anymore. So I was really I think more than anything, I just came to a conclusion that I could be curious and have a beginner’s mind again.

Peter Bowes: [00:12:12] And I mentioned in the introduction that you in your business life have been something of a disruptor, not always accepting the norm, 

Chip Conley: [00:12:20] That’s right.

Peter Bowes: [00:12:20] Can you just describe to me what that’s what does that mean to you?

Chip Conley: [00:12:23] Well, it’s interesting to be a hospitality disruptor. Because it’s sort of an oxymoron, you think of hospitality as being friendly and, you know, congenial and

Peter Bowes: [00:12:33] Right.

Chip Conley: [00:12:33] Maybe in a service mode. And when you think of disruptor, you think of somebody who’s just stirring, stirring things up and maybe upsetting people. So to be to be a hospitality disruptor and twice now, first as one of the first boutique hotel years and then with Airbnb, I think more than anything, what it’s meant to me is being open to new ways of doing things and accepting that lifestyles are changing and how we deliver our experience in hospitality can change, especially incorporating technology. So, I mean, that’s that’s what it’s been, you know, and the evolution as humans evolve and their desire and needs for travel evolve, so should the hospitality industry. But the hospitality industry has historically been extremely conservative. And it’s it’s a bricks and mortar business generally, which means that it changes very quickly. Very slowly.

Peter Bowes: [00:13:32] And of course, this year of all years has probably

Chip Conley: [00:13:35] Yeah.

Peter Bowes: [00:13:35] Been the worst nightmare for the hospitality business.

Chip Conley: [00:13:38] It has and, you know, I still own well, I sold the company, I still own the real estate of nine hotels. And so that’s a that is a curse. Nobody wants to be owning hotels right now. On the other hand, I own a ton of Airbnb stock and Airbnb made a huge comeback in the second half of 2020, such that when it did its IPO in early December, twenty twenty, it went exceptionally well. So thankfully, my Airbnb profits or wealth is helping to fund my hotels that are going down the drain.

Peter Bowes: [00:14:15] So let’s talk about then your current venture, you could say your current area of disruption, Modern Elder Academy.

Chip Conley: [00:14:20] Sure,

Peter Bowes: [00:14:21] What is it, where is it and who goes there?

Chip Conley: [00:14:24] So the Modern Elder Academy is a it is a midlife wisdom school. What the heck is that? Well, we don’t have a whole lot of schools that help people understand how to cultivate and harvest their wisdom in midlife, nor help them understand what they’ve built mastery around. And so that’s what we do. We we are dedicated to not lifelong learning, but long life learning. And that is based upon the premise that people in midlife and later may have a different way of learning and different interest and passion for what they want to learn. You know, what you want to learn at age 30 is different than age 60. But when it comes to the term lifelong learning, it’s sort of a one size fits all. So long life learning is about creating a life that is deep and meaningful as it is long. So focusing on not just the quantity of life your years, but the quality of your life, your happiness and satisfaction and sense of purpose. And so we created it. Given that there’s nothing like it, we created it for the first six months on a beta basis, trying out different things to different cohorts for one week and two week cohorts at our campus, which is on a beachfront in southern Baja in Mexico. So about one hour north of a well-known place called Cabo San Lucas. And turned out people really, really liked it. The number one thing they wanted was a community or an alumni association, which is a good sign. If people said, you know, the food sucks, you know, the hospitality wasn’t good, your program is terrible, then they wouldn’t really want an alumni program or any kind of community. But in fact, everything else went well, which is meant, hey, how do we keep this going? And so for three years now, we’ve been doing that. We now have a modern elder academy online program as well. And we’re just in the midst of creating our first NCAA regenerative community, which is a it’s sort of a 21st century version of a retirement community. And joining us to talk about that for a minute, because I.

Peter Bowes: [00:16:25] It sounds intriguing to me. I was going to say, I suppose the whole ethos of what you’re doing is it’s not only about gaining new knowledge in terms of education and learning, but it is about learning how to be old and how to enjoy those extra years that I as I said at the beginning, that were clearly we are able to achieve if we live our lives in a certain way.

Chip Conley: [00:16:46] The unexpected pleasures of aging. Yes,

Peter Bowes: [00:16:49] That’s it.

Chip Conley: [00:16:50] It is, that is it’s also how to understand how to build mutual mentorship relationships with people younger than you, because I actually think the future of mentorship is not one way from old to young. It goes in both directions. That’s certainly what I learned at Airbnb. They taught me a lot about dequeue digital intelligence and I taught them a thing or two about EQ emotional intelligence, and we were both better off for it. So what I would say is that the program is is really focused on helping people to understand purpose, wellness and community, which is a premise that came out of Stanford getting Dr. Phil Pizzo, who ran the medical school there and then created the Stanford Distinguished Careers Institute. And what they were able to show is that purpose, wellness and community are really the most important things to people after about age 50. So that’s a big piece of it as well. And then we also have incorporated Becca Levy’s work from Yale, who’s been able to show that if you can help people move from a neutral or a negative perspective on aging to a positive one, you add seven and a half years to their life, which is more life added than if you stop smoking in midlife or if you started exercising in midlife.

Chip Conley: [00:18:02] So we’re really focused on not just the longevity piece, but creating great longevity, you know, good happy years, extra years. But it’s not just focusing on diet and things like that. It’s really focusing on the psycho psychological diet, the spiritual diet. Carl Jung was very famous, the psychologist, in saying you can’t leave the afternoon of your life based upon the rules of the morning. And what he was really talking about was the fact that the operating system that defines our life from adolescence to middleescence, middleescence, being around 50 to 55 is the operating system is your ego, and it works for you in certain ways. It may not work for you in other ways, but around age 50 or so, the operating system starts to shift your soul and the operating system of your soul is very different than the operating system of your ego. We have almost nothing in the way of schools, tools, rites of passage or rituals to help people understand that they are moving from a to a stick shift to a manual driving. And we just need to help them with that.

Peter Bowes: [00:19:11] You mentioned, I suppose, the human operating system, I suppose we we evolve to operate until we have produced children, until we are beyond breeding age, and then we really aren’t evolutionary of much use. And that’s why traditionally I am talking hundreds of years ago, but

Chip Conley: [00:19:29] Yes.

Peter Bowes: [00:19:29] That’s why we died when we were much younger. So you could say we are pushing the boundaries now and therefore we do need, as you say, to kind of upgrade that operating system to deal with our new situation.

Chip Conley: [00:19:40] Well, and recognize that for those who want to go back to an era where it was all about reverence of the elders, you know, young people today don’t listen to grandpa, they listen to Google, Googles where all the information is. 

Peter Bowes: [00:19:53] And so we’re not going to get back to that era. What we are going to get to an era, though, is moving from reverence to relevance. And if we can help people in 50 plus recognize that relevance is about being as curious as you are wise, which is the definition of modern, a modern elder, then you can actually learn how to take that wisdom that you’ve developed over the course of your lifetime and create context for it in a evolving world. And that’s the key. And then you can be relevant and the more relevant you are, because in my case, in my mid 50s, I was helping some company that had an average age of 26 become, you know, the global giant in hospitality and travel, which is Airbnb. My if I was just the wise one and everybody just sat at my feet and I just spouted wisdom that that wouldn’t have worked if that’s how I thought it was going to work. Instead, I had to actually be sometimes the beginner’s mind. I didn’t know a darn thing about technology. And this is a tech company, so I need to be as much an intern as I was a mentor, which is why I say a modern elder is also a mentor and a mentor, an intern at the same time.

Peter Bowes: [00:21:10] Yeah, it’s an interesting concept, a couple of questions ago, I jumped in and interrupted you, you are about to go off on a different tangent in terms of some of the programs

Chip Conley: [00:21:18] Oh,

Peter Bowes: [00:21:18] That you do, which sounded intriguing. So

Chip Conley: [00:21:20] Yeah,

Peter Bowes: [00:21:21] Let’s just return to that thought.

Chip Conley: [00:21:22] Let’s just yeah. Quick, quick thought so one of the things we’ve learned here is people want community deeply and they want to come and have an experience, feel a sense of transformation and then potentially say, OK, how do I how do I keep this going? And so we’ve had a gosh of the almost 800 people who have come down here to Baja, about 40 to 50 of them have now moved down here, you know, within the neighborhoods, so to speak, on the beach here. So that’s a lot. And so what we decided, let’s create a regenerative community. So Sun City. Are you familiar with Sun City? OK, famously, Sun City was the sort of the famous first retirement community in the United States. It was 60 years ago. And so Sun City was to retirement communities in the 20th century, what we hope MEA will be to regenerative communities in the 21st century. So what’s the difference between a retirement community and a regenerative community? Well, instead of having a golf course fairway in the nucleus in the center and a clubhouse, you instead have a regenerative farm, which is a step above sustainability. So it’s a farm that actually regenerates the soil and through, you know, really great new research on how and how to do that. So you’re regenerating soil and creating great produce and eating well as a result of that right there in the center.

Chip Conley: [00:22:46] And instead of having a clubhouse for everybody, starts drinking, you know, alcohol at noon for lunch instead. We actually have a midlife wisdom school MBA that can actually be doing workshops. And then beyond that, we have a series of homes. And but instead of those homes being sort of these ranch homes on the golf course fairway that, you know, everybody sort of separated from each other, this is a little bit more of a village. And so you have that as well. And then for those who see it as a second home, they put their home back into the rental pool and then we create sabbatical sessions, which is what we’re doing right now during covid here at MEA. And all of this together is a new concept. And so we have a 2600 acre ranch outside. Well, I can’t tell you where it is yet, but it’s in the U.S. outside of a well-known town that is very popular, where people a lot of people go later in life sometimes and decide to retire there. And we’re going to be doing our first MEA regenerative community there. And we have another one in town that we’ll probably do as well.

Peter Bowes: [00:23:49] It does sound intriguing, will return to my conversation with Chip in less than a minute. You’re listening to the Live Long and Master aging podcast. This episode is brought to you by AgeUp, a new product that helps fill in the financial gaps that are often created. Once you’ve mastered aging and achieve an exceptionally long life, small monthly payments to AgeUp stack over time to create a secure income stream for your 90s and beyond. Contributions to AgeUp are shielded from market swings, and once payouts begin at age 91 or above, they’re guaranteed to lust for life. AgeUp is backed by MassMutual and sold by Haven Life Insurance Agency. You can find out more at Age-Up dot com. That’s Age-Up dot com. I’m talking to Chip Conley, founder of MEA, the Modern Elder Academy. Chip there’s a quotation on the homepage of your personal website young enough to take up surfing, old enough to know what’s important in life. And it’s a quote from your book, Wisdom@Work The Making of a Modern Elder. I’m curious, at what age were you when you really realized what was important to you?

Chip Conley: [00:25:01] I know the good news is I think I’ve always known that I wanted to take a different path than my parents or what was prescribed for me, and that has helped me to take the path that’s been less traveled. But I would say when I had my flatline experience, my late 40s, that was a real wake up call. I think one of the questions we all need to ask ourselves is if we were to die today, what would we regret? What we we regret in terms of what we didn’t do, what we regret about what we did do. I like to call this the box of unlived life or and sometimes I loved life. What is it that doesn’t feel fully baked in our life? So if I died at 47, I would have died a very successful entrepreneur, someone who had learned a lot of leadership. I had I probably had the wisdom of a 75 year old for leadership. But when it came to my romantic or family life, I felt like, wow, I’m like a 17 year old. So I had a lot of wisdom to be learned there. And and so that that was one of the things I learned. So I think that question, though, is what’s unloved or unloved and how might we regret it if we died? Now, in terms of what hasn’t been given enough attention or investment is an important question for us to ask all the time.

Peter Bowes: [00:26:23] And is the goal to get to a point where we’re comfortable enough to say when we’re dying, that we have no regrets?

Chip Conley: [00:26:30] I don’t think well, I think that’s a function of the person I don’t I don’t think that I don’t want to say that someone shouldn’t have regrets. I personally think I will always have regrets because I think without actually having regret that I haven’t been able to iterate from those regrets. Can I can I say so? What I would say is I ever regret of what happened or didn’t happen then. And then I learned from it. And then you could get to a place of saying, well, then I don’t have a regret anymore because actually served a purpose. And yes, that that language and that thinking is simpatico with my thinking. But to say that I had no regrets is to me rather arrogant suggests I lived my life exactly the way I was supposed to live my life. And I don’t think anybody does that. And if you think think that way, then you probably are still, you know, the president of the United States right now because you have a point of view that you don’t make mistakes.

Peter Bowes: [00:27:29] Yeah, it’s an interesting concept, and I think you’re right, we’re all individual and we all view these things in a different way and maybe I can have regrets. We all have regrets, but then maybe get to a point where you reconcile that regret and it isn’t such

Chip Conley: [00:27:43] That’s right.

Peter Bowes: [00:27:43] It doesn’t weigh on your mind as much when you’re 40 or 50 as it does perhaps when you’re 70 or 80 because you you work it through.

Chip Conley: [00:27:51] That’s right, and just know also that when it comes to the subject of regret, I have a book called Emotional Equations and I studied 18 different emotions, including regret and equations for each one of them and regret. The thing to know about regret is that regret of the thing you didn’t do is twice as bad as the regret of the thing you did but wish you hadn’t done. And that’s well documented in social science research. And it has a lot to do with the fact that if especially if it’s a regret is something you could no longer do again, then that becomes painful because you spend the rest of your life bathing in that that mucky water.

Peter Bowes: [00:28:27] Yeah, and I suppose it comes full circle talking about wisdom and acquired wisdom as we age, and I question that eternal question if only we had that wisdom at the age of 20 or 30, when we’re making some of those lifetime decisions, when we’re weighing whether to do this or whether to do that or whether to take that job or whatever the opportunity is. And I think that encapsulates a lot of what you’re doing that, you know, we do acquire this wisdom and it’s a matter of how we use it and how we use

Chip Conley: [00:28:53] That’s right

Peter Bowes: [00:28:53] And how we use it to benefit ourselves and the people around us as we grow older.

Chip Conley: [00:28:56] You know, one of the things I was lucky to learn about wisdom at a young age was I didn’t really have a language for it exactly, but I started a company at 26. I didn’t know anything about the hospitality or hotel industry. I, you know, bought an old motel and that was in a bad neighborhood for very cheap and had had investors who somehow believed in me. And two years into it, we had an earthquake in San Francisco, 1989, and oh my gosh, we had no guests for like four or five months. And I was lost and had no idea what I was going to do. And I was depressed and I pulled out an old journal or a journal someone had given me. It was untouched. And I instead of creating a journal or writing about, you know, all my emotions, I decided to create what I called my wisdom book. And that’s what I called it. I have the first one, you know, from thirty two years ago. And what I did as a as a practice’s every weekend, I would make a bullet point list of the key things I had learned that that week, because what I believed, as if I could actually focus on what I had learned that week, I could metabolize the wisdom from it.

Chip Conley: [00:30:14] And I have no idea how I ever thought of this. I don’t remember the specific dead. I just remember I pulled it out one day, but something led me to doing this. And so for 32 years now, I have had a practice of cultivating, cultivating and harvesting my wisdom. Every weekend I take 20 to 30 minutes max and it is a way to if I was to take Victor Frankel’s book Man’s Search for Meaning and turn it into an equation, it would be despair, equal suffering, minus meaning. And so meaning and despair are almost inversely proportional to each other. So if you can metabolize or digest a challenging thing, you’re going through and say, here’s the things I’ve learned. You’re actually, in essence, creating meaning and, you know, accelerating wisdom. So, you know, you don’t have to be an older person like you and me, Peter, to actually go out and determine how are you going to accelerate your process of becoming wise. I started doing that at age twenty eight and I think anybody could do that at any point in their life.

Peter Bowes: [00:31:19] I can see where you get all the material from with that devotion

Chip Conley: [00:31:23] Right.

Peter Bowes: [00:31:23] To to the thought process into recording

Chip Conley: [00:31:25] Yeah.

Peter Bowes: [00:31:25] Your thoughts over the years material for your books, which is great. We’re recording this episode on the 30th of December. I’m going to publish it in the first couple of weeks of the New Year, 2021, which is a year that can’t come soon enough for so many

Chip Conley: [00:31:38] Yes.

Peter Bowes: [00:31:38] People, for so many reasons. And it’s also one of those times between Christmas and the New Year, the first couple of weeks of the year when we do, I suppose, do what you’ve been doing for a lifetime, and that is think about our lives and think about the wisdom that we’re acquiring and think about how we’re going to live our lives usually in the next few months. And for some people, those new thoughts might last for a few days before those New Year’s resolutions go out the window. We revert to back to how we were. So I’m curious, at this time of the year for you, does it have any sort of special meaning? Does it have any special impetus for you as you move forward to a new year?

Chip Conley: [00:32:14] Yeah, you know, I mean, being able to do the inventory is always a good thing. The thing I tend to do this time of year is instead of a set of resolutions, I actually make a list of my New Year’s resistance’s. What are the things that are resisting that are actually holding me back. So instead of saying, here’s my resolutions, I’m going to do all these things, I say no here. I already know I’m going to do all these things. But there’s something that’s holding me back and an exercise I recently learned that I am going to do this year for the first time to on this particular exercise. Looking at resistance’s is taking something we’ve done before, which is a repeating question five times, but applying a new question. And the question is what am I in fear about? And so then I have a friend of mine ask that question. So, Chip, what are you in fear about or what do you have fear about? And I would say, well, I fear about let’s see, um, how much work it’s going to be to create a regenerative communities and how much time it’s going to take. And then my friend would say, thank you, Chip, what are you in fear about? And ask the same question. And I can’t answer the same way twice. And we do this five times. And the value in doing a repeating question is sort of like an archaeological dig. It forces you to go deeper and deeper and deeper. And what you’ll find is the things that you’re resisting in your life, the obstacles you’re creating, the ways you’re, you know, old habits are getting in the way, often relate to something you’re resisting and something they’re resisting often has something to do with a fear. And, you know, if I kept going on that same path that I was just on with that first one, about how much time I think there might be an element of I’d come to this fear that, you know, I’m I’m I’m just replaying how I’ve lived my life, which is I’m I go out and I attain and achieve and and then I end up feeling like there’s parts of my life that are not getting the investment in time. And that process might get me to a place of saying, OK, well, based upon that, I now have a resolution that I’m going to make sure I’m allocating 25 percent of my hours, my waking hours each week to the following three things that are sort of box of unloved or unlived life elements in my life that I think really need more time. And to me, that makes a lot more sense than going and just saying, oh, here’s five things I want to do this next year I’m going to go do. And then by the end of January, you’re feeling like, you know, you’re feeling terrible because you’re not doing any of them.

Peter Bowes: [00:34:57] Yeah, it’s an intriguing way of looking at it. This is a podcast about longevity with we’ve mentioned healthspan lifespan already in terms of the rest of your life. What aspirations do you have as it applies to getting very old? Where do you see yourself in those? You could call them the twilight years.

Chip Conley: [00:35:16] Hmm.

Peter Bowes: [00:35:17] And for me, the aspiration is to get to that stage and still be vital and active and as healthy as possible and involved and personally involved with with people and living a life. How do you view

Chip Conley: [00:35:28] Yeah,

Peter Bowes: [00:35:28] That time of your life?

Chip Conley: [00:35:29] Well, I have role models, you know, whether it’s Michelangelo who, you know, above his doorway, had something that said, I think in Latin I am still learning. And he lived till age 87, or Peter Drucker, management theorist who quite famously lived until age 95 and wrote two thirds of his 40 books after age 65. Every two years, he would study a topic that had nothing to do with his career and become one of the world’s leading experts in it. I do that. So that’s part of my way of being, is I study topics that have nothing to do with my my career and then ultimately realized, well, it could maybe I could go in that direction or I could write a book about that or as I did with the Emotions book because I wanted to study emotions. So I would just say that my vision of my future is dedicated to curiosity. I think curiosity is probably the most important elixir in life, maybe more important than the physical things you do, even if it is a it’s a spirit that you embody about not being done. And so I think that’s how I’ll be.

Chip Conley: [00:36:38] And I have no clue. You know, if someone had said to me 10 years ago at age 50, chip at age 60, you will have helped to take a little tech company and turn it into one hundred billion dollar company. And you’re going to be called a modern elder and read a book on that. And you’re going to be living in Mexico and creating a modern elsmore academy I like. Are you kidding me? What are you talking about? So I have no idea what my age 70 will be for me 10 years from now. And that’s the beauty of life, is I don’t have the classic three stage life I have to live that. I think it was so well chronicled in the book, The 100 Year Life by Andrew and and Linda, Andrew Scott and Linda Gratton. And I, you know, I love the fact that there will be surprises. Dan Gilbert has a great the Harvard psychologist has a great TED talk about your future self. And he basically showed from age 20 to age 90, people vastly underestimate how much change is coming in their next ten years.

Peter Bowes: [00:37:45] I think the word curiosity is actually perfect because it just encapsulates the idea of wanting to know what happens next and looking forward. And I think that idea of always looking forward to the next day or the next year because you’re involved in something and you’re curious about it and you’re figuring it out.

Chip Conley: [00:38:02] Mm hmm.

Peter Bowes: [00:38:02] I think I just helps us keep going. But the moment that that stops and that excitement about tomorrow, because you’re curious about the world that you’re living in, I think that is perhaps the beginning of the end for a lot of people.

Chip Conley: [00:38:13] Yes.

Peter Bowes: [00:38:13] And that that constant looking forward certainly keeps me going. And and I’ve noticed that in a lot of people I’ve interviewed for this podcast,

Chip Conley: [00:38:20] Well, I totally agree.

Peter Bowes: [00:38:21] Chip, it’s been really wonderful talking to you all the best with your new venture. I can’t wait to hear more detail, and I’m sure we will in the coming months. All the best to you. Thank you very much indeed.

Chip Conley: [00:38:30] Thanks so much. It’s an honor.

Peter Bowes: [00:38:32] I’ll put some details about the Modern Elder Academy and Chip’s books and website into the show notes for this episode. You’ll find them at the Live Long and Master aging website That’s The LLAMA podcast is a Healthspan Media Production. If you enjoy what we do, you can rate and review us at Apple podcasts. You can follow us in social media @LLAMApodcast and direct message me at @PeterBowes. It’s always good to hear from you. Many thanks for listening.

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