526: Learning to Love Midlife with Chip Conley

Listen On

Chip Conley

Do you ever find yourself thinking that your best years have passed you by? It’s a common reflection that many people have as they get older. However, this mindset can lead many people to lose sight of the positive aspects of life and to experience joy and fulfillment.

I’m very excited to share this conversation with Chip Conley. Chip is a bestselling author, entrepreneur, Co-Founder, and CEO of The Modern Elder Academy. His new book, Learning to Love Midlife, helps people understand the upside of aging instead of only focusing on the negatives. In this episode, Chip shares the 12 reasons why life gets richer, deeper, and infinitely more fulfilling as we age.

Chip unpacks those reasons one by one, and you’ll see how they’re not just ideas but practical, actionable paths. You’ll learn how to navigate midlife transitions, find and refine your purpose with each passing year, and see aging not as a decline but as a profound opportunity to create the life you want and make the years that lie ahead your best ones yet.


  • How our brains get surprisingly better with age
  • Mindset is everything when it comes to aging gracefully
  • Expectations minus reality = Disappointment
  • How coming to terms with our mortality pushes us to be present
  • Wisdom isn’t a given with age
  • Purpose is something you do, and something you live
  • The purpose of life is to find your gift. The work of life is to develop it




“Our painful life lessons are the raw material for our future wisdom.”

“Money will make you rich, but time will make you wealthy.” - Chip Conley



Organifi makes the highest quality nutritional products, which are made from whole food ingredients (not synthetic vitamins) that I enjoy nearly every day, and have for many years. Visit Organifi.com/Hal, and use the code HAL at checkout to get 20% off of your entire order. I hope you find something there that you love! :^)


Rise by CURED Nutrition is a natural supplement made from CBD, Lions Mane and Ginseng (among others) that helps boost energy, performance and cognitive function. There’s no caffeine, no jitters and most importantly, no crash. Visit CuredNutrition.com/Hal and receive 20% off of your entire order. They have tons of other products as well, hopefully you’ll find something that works for you. :^)





Reviews for the podcast on iTunes are greatly appreciated and will allow us to get the word out about the show and grow as a community. We read every single review and believe each one goes a long way in helping us make the show even better! If you received value from this episode, please take a moment and rate and review the podcast by clicking here.


Copyright © 2024 Miracle Morning, LP and International Literary Properties LLC

Hal Elrod: Hello, friends, welcome to the Achieve Your Goals podcast. This is your host, Hal Elrod. And if we were playing the word association game and the word you were given or that I gave you was midlife, what word would come to your mind next? If it was crisis, you’d be in the majority. And that is a problem that my guest today, Chip Conley, is on a mission to solve. A New York Times bestselling author, Conley’s seventh book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, is about rebranding midlife to help people understand the upside of this often misunderstood life stage. And he was asked to give his third, not first, not second, but third Ted Talk on the main stage in 2023 on what he calls the midlife chrysalis as opposed to crisis.

Now, after disrupting the hospitality industry twice, most notably as Airbnb’s head of global hospitality and strategy, leading a worldwide revolution in travel, Conley co-founded MEA, Modern Elder Academy, in January of 2018, in Baja California, Mexico, inspired by his experience of intergenerational mentoring as a modern elder at Airbnb, where his guidance was instrumental to the company’s extraordinary transformation from fast-growing startup to world’s most valuable hospitality brand. MEA, again, Modern Elder Academy is the world’s first midlife wisdom school, and has a campus opening on a 2600-acre regenerative horse ranch in Santa Fe, New Mexico in early 2024. Dedicated to reframing the concept of aging, MEA, Modern Elder Academy, supports students to navigate midlife with a renewed sense of purpose and hospitality. And today, that’s what we are talking about with Chip Conley, learning how to love midlife, reframing this stage of your life to be the best stage of your life.

Before we dive in, I want to take just a couple of minutes to thank our two health-related sponsors because health is my highest priority right there with family. Because without my health, I’m not here for my family. I learned that the hard way. First and foremost is CURED Nutrition. CURED Nutrition makes high-quality CBD, CBN, and THC products that are based in nature and is miracle hemp plant that will help you improve virtually every area of your life, from pain to, for me, it’s sleep. I love CURED Nutrition sleep products, their Nighttime Oil and their Night Caps. I take those when I travel. I take them at home. I take it literally every single night to help me get a good night’s sleep. If you want to improve your sleep or any other area of your physical health, head over to CuredNutrition.com/Hal. Again, that’s CURED Nutrition, C-U-R-E-D, CuredNutrition.com/Hal, and use the discount code HAL for 20% off your entire order. And again, sleep for me is crucial. I’m sure it is for you too. And so, their Night Caps and their Nighttime Oil, same product, just two different forms, I highly recommend.

Last but not least, my favorite nutrition brand because they cover the full spectrum of how to wake up with focus using their Focus supplement, their Protein Powder, which I take after my workouts, their Red Juice I take before my workouts. Their Green Juice is their most popular flagship product to give you all the nutrients that you need in one scoop that you mix in water or juice, you name it, head over to Organifi.com/Hal. That is O-R-G-A-N-I-F-I, Organifi.com/Hal, and use that same discount code HAL for 20% off your entire order.

And you can shop by area of life you want to focus on. So, if you want weight loss, click Weight Loss and you’ll see all the supplements that Organifi offers related to helping you curb your appetite, lose weight, improve your sleep, improve your focus, improve your overall health in the fastest, most effective way possible. Again, that’s Organifi.com/Hal and use that discount code HAL for 20% off.

All right, without further ado, I’m so excited for you to meet my friend Chip Conley talking about learning to love midlife. Here we go.


Hal Elrod: Chip Conley, it is good to see you, my friend.

Chip Conley: Hal, I feel really lucky to be here with you, truly. I love your last name.

Hal Elrod: The Rod, Elrod?

Chip Conley: Elrod. There used to be an Elroy in The Jetsons. And so, it’s way, way earlier than your time, but when I see Elrod, I think Elroy.

Hal Elrod: I used to have a friend that called me Elrod Hubbard, just some sort of play on the L. Ron, yeah. No, I appreciate it. Well, I’ll tell you, I’ve been watching. I watched your TODAY Show appearance, which was recent. Congrats on that, by the way. Very exciting. Hoda is, like, your biggest fan. She was fangirling. And I love Chip and I love his work and every– I mean, she was just going off. That was cool. And then I also watched three of your TED Talks today. And I want to say these aren’t TEDx Talks. These are the big stage, right? These are TED Talks. And I was thinking, I didn’t go down the rabbit hole to see, but I’m like, “Who has not one, not two, but three TED Talks?” So, yeah, I think that you have a lot of value to add.

And actually, I want to start with something that you said in the TED Talk or one of the TED Talks, and millions of views on these TED Talks, so you’ve inspired a lot of people. And you said that, you actually asked the question, “Can we make aging aspirational?” And I wanted to hear what you thought because I know a lot of people, it’s like, “Oh, I’m getting older. My best years are behind me.” The word midlife, I love how you say it. If you’re playing the word association game, crisis comes right after midlife, right? So, talk about this. What does it mean to make aging aspirational?

Chip Conley: Well, here’s the thing. First of all, how old are you, Hal?

Hal Elrod: I am 44. So, I know, I’m in your target market.

Chip Conley: So, for those, I mean, I hope everybody’s seeing Hal. Hal has the best skin, like, where did that skin come from, my friend? It’s amazing. Well, you know what? We all age differently. And I’m 63. But the way we talk about aging is, as if it’s not growing, interestingly. When you’re talking to a 15-year-old and saying to a 15-year-old, “Oh my, how you’ve grown,” you would never say that to a 50-year-old because they think we’re talking about their waistline.

But we’re growing in our lives. In all kinds of ways, they’re not visible. We’re growing culturally and intellectually and spiritually and emotionally and relationally and mentally. And there are many parts of our lives in which things get better as we get older. When it comes to our physical body, that’s less the case. Just as you got comfortable in your own skin, it started to sag.

But the reality is that, even our body can get better with age, certain parts of our body can. Our brain can, for one. Now, short-term memory gets worse with age. But our crystallized intelligence, our ability to trust our intuition, our ability to think systemically and holistically and go from left brain to right brain more quickly, we’re more adept at that left brain/right brain tango or four-wheel drive of the brain as we get older up until our early 70s.

So, what I wanted to do with this book is I wanted to help people to see that there are a lot of anti-aging messages and products in the world. There aren’t a whole lot of pro-aging messages. And I wanted to point out that there are 12 reasons why life gets better with age, based upon not just social science but the over 4,000 people that I’ve interviewed who are all MEA alums, which we’ll talk about, the world’s first midlife wisdom school. So, that’s why I did it. And one last thought is Becca Levy at Yale has shown that when people shift their mindset on aging from a negative to a positive, they gain seven and a half years of additional life, which is remarkable.

Hal Elrod: Wow. Yeah.

Chip Conley: It’s more like additional life if you stop smoking or start exercising. So, having people think about aging as not just a negative thing, but as having some upside as well, unexpected pleasures of aging, was part of my intent with this book.

Hal Elrod: I love it. So, yeah, the book is Learning to Love Midlife. And I’m actually writing, you probably don’t know this, but I’m writing a book called The Miracle Morning for Seniors right now. And so, I’m excited. I’m at the early, right? I think you call midlife, it’s the 40s, 50s and 60s, right? I’m 44, so I’m on the early, early side of that. And I want to actually go back a little bit because for you, I know that you started this work, or part of what inspired this work is that you had friends in their midlife, 40s and 50s, that committed suicide and took their own life. Can you talk a little bit about that experience? What that was like for you? And how that led to this work and to this book?

Chip Conley: Yeah. In my late 40s, during the Great Recession, I lost five male friends to suicide, ages 42 to 52. And I was really going through a difficult time myself. At the time, I had no idea that there was this thing called the U-Curve of Happiness, which got popularized a few years later, which shows that basically, from our early 20s to around 45 to 50, there’s a long, slow decline in life satisfaction. Hal, I hope you don’t mind, you’re at 44, 47.2 is the low point. Your mileage may vary. But these are just averages.

But there’s a lot of reasons why that there’s this long, slow decline in life satisfaction. And so, I got curious about midlife because I was like, well, I’m not enjoying my late 40s either. What’s going on here? I got to the other side of it. I had an NDE, a near-death experience, where I had an allergic reaction to an antibiotic and I died multiple times over 90 minutes. And so, long story short, I got to the other side, sold my company at the bottom of the Great Recession, and had some space in my life.

And then I went through my 50s, and my 50s were spectacular. I was the modern elder to the founders of Airbnb more than 11 years ago when they asked me to come in and help their little tech startup. They wanted me to help sort of guide the rocket ship. And it was a beautiful experience. They called me a modern elder because I was twice the age of the average person there, but also because they said a modern elder, someone who’s as curious as they are wise. I was like, “Ooh, interesting. The alchemy of curiosity and wisdom.” And I loved my 50s.

So, in my late 50s, I decided to create the Modern Elder Academy (MEA). And I started really getting curious about midlife because there’s not a lot of research that’s been done on midlife. And lo and behold, I ended up deciding to write this book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, because I wanted to help people to see that there’s a bridge from the rough part of midlife which does exist, and we can talk maybe about why that exists, to the other side of midlife, where people, according to the U-Curve of Happiness, get happier in their 50s than their 40s, 60s than 50s, and 70s than 60s. So, if you could get over this bridge over troubled water, you can get to the place where actually life gets better with age.

Hal Elrod: Yeah. My mom is, I think, 67, 68. But yeah, she’s just having the time of her life. She’s bright, I mean, she says she’s the happiest she’s ever been. She’s energetic. She goes, she dances, she does karaoke. So, you mentioned you alluded to some of the reasons, like what are the reasons that that period of 47.5, that decade in there, is so difficult for people?

Chip Conley: So, what’s going on often for people in their mid to late 40s, and it can happen earlier than that and later than that as well, is you’re coming face to face with disappointment equals expectations minus reality. So, let me say that again. Disappointment equals expectations minus reality. So, if you have expectations of one level and then reality is below that, the difference between the two is disappointment.

And for a lot of people, it’s around 45 or so, they look at all their hopes and dreams that they had in their 20s. And they can start to say, like, “I’m not going to run for office. I’m not going to be mayor of San Francisco, like I thought I might be,” or “I’m not going to climb Mount Everest.” It doesn’t mean you still don’t have the opportunity to, but you can start to see the window closing. And if these are things that really matter to you, then that can be disappointing.

Brené Brown is a friend of mine, the famous sociologist who says, “It’s a midlife unraveling.” And what she means by that is that you’ve– when I first heard her say it, I said, like, “Brené, no one wants a midlife unraveling. That sounds terrible. It’s like you’re losing your mind.” And she said, “Look in the dictionary under the word ravel and you’ll see that something that’s raveled is so tightly wound, you can’t get undone.” And that’s a lot of the way people feel in their mid-40s is they have the spinning plates phenomenon. They’ve got so much going on, so many obligations they’ve been accumulating. They have children, they have all of this, and then they also have the sense like they’re not meeting their expectations. And we need to unravel that.

And by unraveling it, it means you start to get clear on what’s important to you. And maybe you start to say, like, “It’s time to edit.” At MEA, we call it the Great Midlife Edit. Because the first half of our life is about accumulating and the second half of our life is about editing. But nobody told us in midlife, that’s part of our job is to figure out, okay, what do you let go of? What else is going on around that time? You start to get realistic about your body. Your body is this rental vehicle that you were issued at birth. And by the time you get to your mid-40s, there’s a lot of mileage on that rental vehicle. And for a lot of people, that can be frustrating.

And finally, there’s a lot of death that starts to become more apparent to you in your late 40s, whether it’s family members passing away or your own potential health diagnosis that’s an issue. And so, you start to notice mortality as something that’s on your mind. So, those are all the things that are not going well. But then, frankly, on the other side of that, there are these 12 reasons why life gets better with age that actually start to help you feel better.

Hal Elrod: So, can we unpack some of those? What are some of the themes in the book, Learning to Love Midlife?

Chip Conley: Well, there are five different categories. There are the body, the physical side, then there’s the emotional side, the mental side, the vocational side, and the spiritual side. So, I’ll maybe take one example from each of those five different categories knowing that there are 12 reasons overall, but I’m only going to focus on five right now. The first one is an interesting one. We have really bad longevity literacy. The average person who comes to MEA, this midlife wisdom school, is 54, and the average age, I think, they’re going to live to is 90. But they’ve never done the math to realize that 54 is exactly halfway between 18 when you became an adult and 90 when you may die. So, you have half of your adult life still ahead of you. That’s right. And we sort of think like at 54, oh, I’m going out to pasture.

So, one of the positives and it’s starting to become more clear is that in a world in which people are living longer and a growing number of people are living to 100 that when you start to realize that you have that much life still ahead of you, you can start to actually ask the question, 10 years from now, what will I regret if I don’t learn it or do it now? And so, it gives you a sense of seize the day of, like, okay, one of the things that gets better with age is if you start to realize you have a lot more time ahead of you, you start to actually get maybe a little bit more focused on not the future but on the moment. What can I do now?

One of the great things about aging is you start to realize, “Okay, I’m going to seize the moment.” And so, mortality is, in essence, death is a great organizing principle for life. Okay, let’s go to the second one. Under emotions, our emotional intelligence grows with age. Our IQ does not, but our EQ does. Pretty conclusively, our emotional moderation improves with age, and we learn how to take things less. Personally, we care less about what other people think about us as we get into later in life. So, there are a lot of things around our emotions that improve, and learning how to put the distance between stimulus and response, actually, whether it’s through mindfulness activities or just through not taking things so seriously, has another benefit. And all of the things I’m going to talk about here are what I’ve seen in the 4,000 people who’ve come through MEA, but also, what social science has proven and what our faculty has shown.

Thirdly, let’s go to the next category, which is the mental category and wisdom. Now, wisdom does not always grow with age. I know some 30-year-olds who are wiser than some 70-year-olds, and that’s because they’ve learned how to metabolize their life experiences. I’d like to say that our painful life lessons are the raw material for our future wisdom. So, having said that, one of the things that people start to realize is, oh my gosh, I have the pattern recognition to say I’ve seen this movie before. Meaning I have the intuition to say I know the right answer here because I’ve been on the planet long enough to understand that my intuition is telling me something, giving me some indications of the right decision here. I’m 63 today, and I would say I make much better decisions at 63 than I did at 33. And that’s primarily because I’ve built some wisdom along the way. And I can actually even talk about wisdom practice after I go through these five and if you want to go to those, but I’ll come back to that.

Fourth category of what gets better with age, on the vocational side, is we start learning how to curate some time affluence into our lives because if we can actually get off the treadmill, often it’s around midlife that we start to see successism in our life. Now, what is successism? Successism is when someone else’s definition of success has been imposed upon you, and you realize that maybe your definition of success is different than that. Now, hopefully, you figured that out in your teens or your 20s, but for a lot of people, they don’t figure that out until their 40s. And they realize, “I have been running up this mountain, but it’s not my mountain. I don’t love this mountain. This is my parents’ mountain. This is my community’s mountain. This is not my mountain.” Or like, my valley, it doesn’t even have to be a mountain.

And so, you can start to look at your life and say, like, “How do I spend my time differently, so I have some time affluence?” Money will make you rich, but time will make you wealthy. And again, as you get into midlife and beyond, you start to value time more because you have less of them.

Hal Elrod: Less of it, sure.

Chip Conley: In the future, and therefore, you want more of it in this moment. So, time affluence becomes a thing. And then finally, the fifth category, spiritually, lots of evidence that spiritual curiosity, spiritual intelligence improves as we get older. What I like to say is, I like to quote Richard Rohr here, who’s on our faculty, famous Christian mystic, as well as Carl Jung, who both said basically the same thing, “In the first half of our life, our primary operating system is our ego.” For all kinds of good reasons, it’s what individuates us. It’s what propels us forward. It’s what gives us a sense of who we are.

But it’s around midlife that actually, the primary operating system in our life shifts from the ego to the soul. But nobody gave us operating instructions or gave us a warning this was coming. And I see it all the time in people in their 40s, 50s, 60s who start being more curious about the meaning of life and things beyond themselves. And so, one of the reliefs is, like, oh my God, I no longer have to live in the ghetto of my ego. My ego is here and it will always be here. But it’s now servicing the soul as opposed to the opposite, the soul servicing the ego. And so, I could go on to the other seven, but I’ve given you five of the 12 reasons that life gets better with age. And because those exist, that’s part of the reason why we get happier after age 50. Life begins at 50.

Hal Elrod: Yeah, something I realized recently that kind of a different way of framing what you’re talking about, for me, it hit me recently. And I don’t think I went through a midlife crisis, but maybe I’ve had glimpses of one coming, I don’t know. But I realize that when you’re younger, the younger you are, the more life exists as pure possibility. And the older you are, kind of the less that it does right now. And what happens is, I think, you have now possibility with every passing year is replaced with hindsight. And that’s where regrets are born. You’re looking back, you’re like, “Oh, I wish I would have done that differently. I should have made a different decision.” Whereas when you’re 20, even if you’re like, “Oh, I should have done that differently, but who cares? I’m only 20, I’ve got my whole life ahead of me,” right?

So, I guess, I want to ask you, I’m not sure how to frame this question. I’m 44, but let’s say someone listening 50, 60, whatever, and they’re like, “I’ve got some regrets.” My life, like you said, the disappointment, expectation doesn’t meet my reality. I’m not where I want to be. I’m not sure what the future holds. I don’t have a sense of purpose. So, I would imagine, I think that’s a large segment of our population that are lacking this clarity, this purpose and meaning and etc., broad question and let’s just see what comes up for you, but what would you say to that person? I’m like, “Chip, hey, man, my life’s not where I want it to be. And I don’t know that it’s going to go anywhere better, and I just feel unhappy and stuck.”

Chip Conley: Well, you just described the 4,000 people who have come to our program, man. Let me talk about the program and then tell you what I would say to them. So, six years ago, I started the Modern Elder Academy, sort of doubled down on the term modern elder because that’s what they called me at Airbnb. And it’s someone who’s this curious of their why. So, I wanted to say, like, “Okay, you know what? You can be an elder at any age.” Tom Brady was an elder in NFL. You can be a fashion model, an elder at 30, a software engineer in Silicon Valley and being an elder at 35. So, it’s a relative term. So, started the world’s first midlife wisdom school, created a campus in Baja on the beach. Now, having…

Hal Elrod: So, it’s an in-person school.

Chip Conley: It’s an in-person school, and we have a school in Santa Fe, New Mexico on 2,600 acres of regenerative horse ranch. So, it is an in-person school. People come for a week, and they go deep. And so, average age is 54, as I said earlier, and it’s people of all walks of life because we have financial aid as well as full tuition. So, long story short is people come all the time feeling stuck up in 40s, 50s, and 60s.

So, the curriculum we have focuses on navigating midlife transitions, cultivating purpose, and learning how to own your wisdom while reframing your relationship with aging. It’s learning how to feel better about it. What I want to just say is that two things related to your question. I like to ask people the following because this is the breadcrumbs to meet your purpose. Often, people get worried they don’t have a purpose. Well, find something that you’re purposeful about. Forget about the noun of purpose. Focus on the verb of being purposeful.

So, the first question I would ask is, what in your life are you agitated about, excited about, curious about, and/or something through childhood or your early adulthood that you were passionate about but sort of got lost? And that question, it often brings something up for a person. So, a person might feel stuck or, like, I don’t feel like I know what I’m doing. And it’s like, okay, what excites you? What agitates you? What makes you curious?

But I’ll tell you a quick story. There’s a woman. She was a litigation attorney and she was in the Bay Area, and she’d been doing it a long time. She was 60 years old. She didn’t like what being a litigation attorney was doing to her. It made her conflict seeking, and she liked to argue a lot. And she had lost a husband to divorce, partly because of it, she thought. And so, she came to MEA stuck because she was like, “I’m really good at this and I hate it. And I’ve been doing it for too long and I have no idea. And I don’t want to retire. I don’t know what I’m supposed to do next.”

So, ultimately, in the course of the workshop, we asked her this question and we got to the place of like, oh, when she was a child, like a teenager, she loved cooking pies with her grandmother in her grandmother’s kitchen. She loved the smells. And as an adult, she’s realized that whenever she’s in a new town or a new neighborhood, if she sees a bakery, she always walks inside. She wants to smell it. She wants to see what they have. But it had not registered to her. It had nothing to do with her career as a litigation attorney.

By the end of her week with us, she realized, “I’m going to go learn how to become a pastry chef. I am going to take that baby step. And if I like it, I am going to learn it. I’m going to figure out how to wind down my litigation practice, and I’m going to go and create a bakery in my neighborhood, because in my neighborhood, there used to be a bakery, and in COVID, it closed. And there’s no bakery in my neighborhood.” And so, that’s what she’s doing now.

So, that is an example of how do you unlock something for someone when it’s not obvious. Similarly, there’s a beautiful quote that I like to say, which is the purpose of life is to find your gift. The work of life is to develop it. And the meaning of life is to give it away. The purpose of life is to find your gift. What if we shifted the word gift to wisdom? The purpose of life is to find your wisdom, to discover it. The work of life is to develop it. And the meaning of life is to give it away.

Part of what we do at MEA is help people figure out what is their gift, what is their wisdom, what is their mastery. Because what I learned at Airbnb when I joined Airbnb, I had been a boutique hotelier for 24 years, started one of the first boutique hotel companies in the United States, grew it into the second largest in the US, have 52 boutique hotels. But a lot of what I’d learned along the way felt really obvious to me. So, when I sold that company and then had a little bit of time off, and then joined Airbnb as the in-house mentor to the founders, a lot of my wisdom was the kind of stuff that I felt like, “Oh, everybody knows that.” But no, they don’t. And especially in an organization where there were some brilliant technologists who knew a lot about DQ, digital intelligence, but not a lot about EQ, emotional intelligence, or about corporate strategy, or frankly, about hospitality and travel business industry that we were just…

Hal Elrod: That they were now in, yeah.

Chip Conley: That’s right. So, helping people to see then the not obvious to them but obvious to other people, gifts and wisdom you have, is a real valuable thing. And often, your friends don’t notice it either because they’re just like you.

Hal Elrod: Yeah, yeah, that’s true. I had a coach that taught me that years ago that people, we take for granted the wisdom or knowledge or experience that we have when there are infinite amount of people that don’t yet have that and that would love to learn from us. You mentioned earlier a wisdom practice that you could share and to circle back to that. So, I’d love it if…

Chip Conley: You’re good, Hal. You’re good. Yeah. So, when I was 28, I had been CEO of my company for two years, and I was sort of an idiot. I mean, like a 28-year-old CEO at one hotel in a bad neighborhood, it used to be a motel, where people pay by the hours. But it became a rock and roll hotel. And I was doing my best. But I limped into the weekend one weekend where, like, I just felt like an idiot. And I’ve been complaining to a friend of mine and he says, “Well, just start writing in the journal.” I was like, “Okay, I’ll write in the journal.”

So, I took a journal off the wall that I hadn’t written in, and instead of actually writing emotional stuff of what I was feeling, I wrote on the front of it my wisdom book, like out of the blue. I mean, who knew I’d be creating a wisdom school many, many years later? So, I wrote on the front, and I started a practice that I’ve been doing for 35 years, and that is at the end of every week, going into the weekend, I spend 20 to 30 minutes. Now, I do it in a Google Doc.

But back then, for many, many years, I did it in these journals and I would write down four, six, maybe eight different lessons I learned that week, something that, just whether it’s personally or professionally, maybe it was a painful lesson. Maybe it’s something like, “Oh, okay, now I know that.” And then I’d write down what the lesson was and how it’s going to serve me in the future.

So, let me use an example. The reason I started doing this in 1989 was because the Loma Prieta earthquake came along, which basically devastated the San Francisco Bay Area and nobody’s coming to town. And my only hotel was in San Francisco. And like, now it was empty. And I didn’t have a lot of cash flow to be able to cover the losses. And so, I had a really creative idea that I wanted us as a leadership team to buy into, to help bring business to the hotel. And so, I brought it up at a leadership meeting. And I was the owner of the business and I was the CEO. So, like, of course, everybody should say yes to Chip, but no, I had two critics on my team who are natural born critics. And they came up with all the reasons why my idea was a bad idea.

And so, everybody else is just like, “Yeah, let’s not do that.” And I still thought it was a good idea, but at that point, I’d made the mistake of introducing it to everybody, when in fact, my lesson was, if there are a couple people who are going to not like your idea, present it to them first one on one so they can get their fingerprints on it, so that when you present it to the whole group, maybe they’re actually going to be supportive. Now, to me, at 63 today, that’s so f*cking, excuse me, so obvious. But at 28, that wasn’t obvious. So, that became a lesson and it was going to serve me in the future.

So, if our painful life lessons are the raw material for our future wisdom, finding a wisdom practice that allows you to actually make sense and metabolize your experience is important. I do this on our leadership team. I’ve done it throughout of these, my hotel company, at Airbnb, at MEA now, where once a quarter, on the leadership team, each of us will say, “Here’s my biggest lesson of the quarter and here’s how it’s going to serve me in the future.” And so, let’s say there’s eight people on the team and each of eight of us say what it is. And then as a group, we say, “What was our biggest team lesson for the quarter?” And we actually say how well it helps us moving forward.

That exercise has helped so many of the teams I’ve been involved in to not just feel like they have the candor and vulnerability to talk about what the lesson was of the quarter, but actually, they shared it with other people. So, their lesson is my lesson. And so, I would just say, we are moving into an era where knowledge is commoditized. We have AI and all of the world’s AI.

Hal Elrod: Is that ChipGPT on your website?

Chip Conley: There is a ChipGPT on the Chip Conley website. So, all of my content is right there. I have a daily blog and all of my books are right there. So, you can ask me anything without even meeting me. What we’re moving into in is the wisdom era. And the knowledge era has been very good, but it’s all commoditized. And what’s valuable today is learning how to make sense of our wisdom. And wisdom is very much of a human quality. A bot is not necessarily going to be wise. It will be smart, but not necessarily wise.

Hal Elrod: How do you define the difference?

Chip Conley: Knowledge, you accumulate and that you could learn the knowledge, the capital of Paraguay is fill in the blank. But wisdom is based upon personal experience. Knowledge, you can also be a knowledge expert in a particular domain but be clueless about a bunch of other things. When you’re wise or something has wisdom built into it, it has personal life experience and human qualities built into it. So, knowledge is localized. Wisdom is sort of globalized in the sense that when someone has wisdom, they have wisdom across domains. And so, also knowledge is something you accumulate, so you add, whereas wisdom is something you distill. It’s taking a bunch of information and distilling down what’s essential.

Hal Elrod: And real quick just to circle back to something you said earlier, which is you talked about how our memory declines in our older age. And actually, I have a brain injury from when I was 20. So, I have probably the memory of an 80-year-old at 44 now. But the point being, what’s interesting to me is that even if your memory is not as good as you get older as you’re in your midlife or beyond, the wisdom stays with you. So, that’s just a distinction that came up for me as you were talking, right? It’s that, like, I don’t remember a lot, but I do feel like I’m pretty wise for a 44-year-old. And to your point, it is all based on life experience. And it’s like, “Oh, I’ve been there, I’ve done that, I overcame that. Here’s what I learned from it.” But I can’t tell you the capital of Paraguay or what I did yesterday without checking my schedule and so on and so forth. So, that was an interesting distinction for me, is that if you can understand that as you get older and if your memory is not good and that’s frustrating, but you realize that wisdom is within you and always available.

Chip Conley: Yeah, I mean, wisdom and intuition have not been studied very much. This is one of the things that we’re working on right now is like, how is wisdom different than intuition? There’s similarities. I think intuition is a form of wisdom. It’s not the only form. But I think we’re moving into an era where wisdom workers will be maybe as valuable as knowledge workers.

Hal Elrod: Yeah, sure. Interesting. Well, especially with ChatGPT or ChipGPT, that they have the knowledges, like you said, commoditized. Wisdom is not. You mentioned MEA a few times now. I remember, correct me if I’m wrong, but it stands for Modern Elder Academy?

Chip Conley: That’s correct, it does.

Hal Elrod: The first one was in Baja, Mexico. Did you say?

Chip Conley: Baja on a beach. And we have usually about 24 people in a workshop, and it lasts a week and we have them every week of the year. And we have workshop leaders, everybody from Esther Perel to Dan Buettner who started Blue Zones, to Michael Franti, the musician, so all kinds of well-known leaders. And then we have our own core workshops as well. And then in Santa Fe, we have a campus opening in the spring that will also be doing workshops as well.

Hal Elrod: Got it. Okay. Yeah, I had an ADHD moment and I got curious, so I googled it and looked up the website, MEAWisdom.com, while you were talking. I was still listening, but it’s beautiful, man. This is pretty cool, MEAWisdom.com. So, if anybody’s interested in that, that’s where you can…

Chip Conley: And you can find my blog there. So, I have a daily blog called Wisdom Well, and if any of this is interesting to you, you can find the blog there and subscribe. And you get an email from me daily for free. But what I’ll just say is, like, Hal, most of us fuel up on a lot of our knowledge and education early in our life. And by our mid-20s, we’re sort of like driving our car of life through life. And we need some refueling in midlife. So, think of this as, like, a midlife refueling, a pit stop that allows people to not just figure out who they are, what they want to do, etc., but also how they understand the life stage of midlife, which is a much-derided life stage because of midlife crisis. And so, that’s where the world’s first midlife wisdom school and have gotten all kinds of awards for our program.

Hal Elrod: Well, this reminds me, you’ve shared a few quotes. One quote that comes up for me in this conversation is Wayne Dyer, “When you change the way you look at things, the things you look at change.” And I found that quote to be such a driving force in my life, where I’ll be, whether it’s sometimes I feel like, oh, life’s not good right now, this is going wrong and my business is a mess, and I’m stressed over this, right? And then all of a sudden, I have a conversation with a friend, or I read a book like Learning to Love Midlife, and it’s like, oh, I see this totally differently. It can also be in a relationship with a person in my life, right? Like, oh, this person is so frustrating. And then you look at that person differently, or you look even through the eyes of empathy and you’re like, oh, they’re just hurting. I’m sorry that I felt that way toward them.

So, to me, that even just the title of your book, Learning to Love Midlife, to me, it’s like, wow, this is a book where by the time you’re done reading it or while you’re reading it, you’re going to probably see midlife in a totally different way that’s going to upgrade the quality of your life and how you feel about every day and every moment in yourself and your future and the present. So, any closing words for anybody listening that you’d share?

Chip Conley: Yeah. You don’t have to go through this alone. I mean, a lot of people, a lot of times in midlife, we don’t go through adolescence alone, although sometimes people do. But generally, we go through adolescence as a peer group and we’re trying things for the first time and we get through it. When we’re going through mid-adolescence, a word that describes midlife, a time when we are going through hormonal, emotional, physical, and identity transitions, just like adolescence was full of that, mid-adolescences too, you don’t have to be doing it alone. You can have a cohort of people who are supporting you during that era.

Unfortunately, as was true for my five male friends who took their own lives, a lot of people feel like they’re getting the game of life wrong, and they feel like an idiot because they’re disappointed with their life. So, highly recommend that people look at whether it’s reading my book, reading my blog, coming to MEA, we have online programs to check out any of that or check out whatever you need to actually make sure that you have other people in your life who are the emotional insurance for you on a rainy day.

Hal Elrod: What is the best place online for people to find you and find out about all the work that you’re doing?

Chip Conley: MEAWisdom.com, ChipConley.com, but I post each of my daily blog posts on my LinkedIn profile. So, I have a very active LinkedIn profile and community, and so, people can check that out as well.

Hal Elrod: Very cool. Well, Chip, thanks for the work that you’re doing, brother. As an early midlifer, I really appreciate it. And I know that so many people listening, I mean, that is our target. The majority of people that are part of the Miracle Morning Community and listeners to the podcast are age 40 to 60. So, I mean, it’s literally right in that age range. So, when I had the opportunity to bring you on the show, I was really excited because I knew this is perfect for our listeners and my audience. And thank you so much, brother, for being here. I appreciate you.

Chip Conley: Thank you for all you do, Hal. I really appreciate it as well.

Hal Elrod: Awesome. Well, goal achievers and members of the Miracle Morning Community, I love you so much. And check out Chip’s book, Learn to Love Midlife. Head over to MEAWisdom.com to check out the Modern Elder Academy. And I love you so much. I’ll talk to you next week.

Leave a Reply

Your email address will not be published. Required fields are marked *


Related Posts

Eric Stranghoener

543: How to Integrate Miracle Mornings to Transform Your Workplace with Eric Stranghoener

Eric Stranghoener, the CEO of RubinBrown, is here to explain how integrating The Miracle Morning into their corporate culture has turned the company into an extraordinary personal and professional development platform and how you can do the same for your workplace. Their first Miracle Morning “huddle” was joined by over 200 employees and has since become an integral part of dozens of employees’ personal and work growth.

Read More »

Interested in Hiring Hal Elrod To Speak at Your Next Event?

Subscribe to Hal's Podcast

Have you downloaded the App?

Have you read the book?

Have you watched the movie?

Custom Bulk Order Request

Want to buy larger quantities for your company, team, church, school or other organization? Click here to submit this form and let us know how many copies.