The Light Watkins Show

190: Embracing Midlife as a Springboard for Growth and Transformation with Chip Conley

January 17, 2024 Light Watkins
190: Embracing Midlife as a Springboard for Growth and Transformation with Chip Conley
The Light Watkins Show
More Info
The Light Watkins Show
190: Embracing Midlife as a Springboard for Growth and Transformation with Chip Conley
Jan 17, 2024
Light Watkins

In this week's episode, we shed new light on midlife, transforming the dreaded "crisis" into a phase of immense growth and self-discovery. 

Our guest, Chip Conley, a seasoned entrepreneur and founder of the Modern Elder Academy, shares his inspiring journey and profound insights into making midlife a period of unparalleled transformation.

Discover how Chip's personal and professional challenges led him to create the world's first midlife wisdom school. This episode delves into the stages of midlife, comparing it to a caterpillar's metamorphosis into a butterfly. We tackle societal pressures, the importance of nurturing friendships backed by science, and the deep fulfillment of creating work that resonates with our souls.

Listen as we explore the trials of midlife, from personal loss to identity crises, and how these challenges can catalyze profound reflection and growth. We also discuss rediscovering purpose, pivoting towards a life aligned with our core values, and the concept of 'middle-essence,' drawing parallels between adolescence and midlife.

Finally, we share transformative experiences from the Modern Elder Academy's Baja retreats, highlighting the power of vulnerability, awe, and supportive communities. This episode isn't just a conversation; it's an invitation to view midlife with potential and positivity. A must-listen for anyone navigating or looking forward to this transformative life phase, offering wisdom, support, and inspiration. Join us and redefine your midlife journey!

Send us a text message. We'd love to hear from you!

Show Notes Transcript Chapter Markers

In this week's episode, we shed new light on midlife, transforming the dreaded "crisis" into a phase of immense growth and self-discovery. 

Our guest, Chip Conley, a seasoned entrepreneur and founder of the Modern Elder Academy, shares his inspiring journey and profound insights into making midlife a period of unparalleled transformation.

Discover how Chip's personal and professional challenges led him to create the world's first midlife wisdom school. This episode delves into the stages of midlife, comparing it to a caterpillar's metamorphosis into a butterfly. We tackle societal pressures, the importance of nurturing friendships backed by science, and the deep fulfillment of creating work that resonates with our souls.

Listen as we explore the trials of midlife, from personal loss to identity crises, and how these challenges can catalyze profound reflection and growth. We also discuss rediscovering purpose, pivoting towards a life aligned with our core values, and the concept of 'middle-essence,' drawing parallels between adolescence and midlife.

Finally, we share transformative experiences from the Modern Elder Academy's Baja retreats, highlighting the power of vulnerability, awe, and supportive communities. This episode isn't just a conversation; it's an invitation to view midlife with potential and positivity. A must-listen for anyone navigating or looking forward to this transformative life phase, offering wisdom, support, and inspiration. Join us and redefine your midlife journey!

Send us a text message. We'd love to hear from you!


“CC: Midlife is a transformational period. Sometimes it requires us to get knocked up the side of the head with something that's unfortunate; bad circumstances, in my case, having friends commit suicide, having a partner leave me, having my foster son wrongfully going to prison, running out of cash in my company. It all happened at the same time. 
 There are times I think in midlife when there's so much happening at once that it forces you to get on your knees and say, okay, I surrender the way I've been doing things isn't working. I need help with doing it a new way.”


[00:00:34] LW: Hey friends, welcome back to the Light Watkins Show. I'm Light Watkins. And I interview ordinary folks just like you and me who've taken extraordinary leaps of faith and the direction of their path, their purpose, or what they've identified as their mission in life. And in doing so, they've been able to positively impact and inspire the lives of many other people who've either heard about their story or who witnessed them in action or people who've directly benefited from their work.

And today I'm back in conversation with Mr. Chip Conley, who's one of my favorite humans on the planet. For those of you who may remember, he was on the podcast back in episode 125. For those of you who don't remember, chip was the guy who took that leap of faith in acquiring the CD Hotel in San Francisco and ended up turning it into this beautiful boutique hotel called The Phoenix, which ended up being frequented by several famous Rock and Roll musicians. And his portfolio of hotels expanded over the next several years to over 50 properties. 
He also had this mentorship with Southwest Airlines founder, Herb Keleher. And in that episode, he talked about all of the ways to create a fruitful, meaningful, productive mentor-mentee relationship from both sides. 

And then in his fifties, chip had a near death experience. He was giving a speech, his heart stopped a few times. He had to be brought back to life. And the combination of that experience, a friend's suicide, selling his hotels, the mentorship wisdom, all of that culminated into this project that chip developed called the modern elder academy in 2018. 

The Modern Elder Academy is the world's first midlife wisdom school that is dedicated to bringing light and space into the midlife atrium through long life learning as opposed to lifelong learning, and I've actually had the honor of visiting and even presenting at the Modern Elder Academies, Baja, Mexico campus in the summer of 2023, where I got to see firsthand how powerful that programming that Chip develop is when it comes to re-imagining what it means to be in midlife.

And most recently, Chip has released, I don't know if this is eighth or ninth book, but he's written a lot of books. And this one is called Learning to Love Midlife, which exposes the branding problem that is midlife. And we talk in this particular episode about how to know which stage of midlife you're actually in, whether it's the caterpillar stage, the chrysalis stage, or the butterfly stage. 

We also talk about the anti aging industrial complex and how to know if you are making choices in your life that are influenced by that complex and how to regain your Agency when it comes to optimizing for midlife. 

We talk about friendship and why during midlife friends aren't a nice to have, they are a need to have, and there's science that backs this up. So Chip and I chopped it up about all kinds of topics related to midlife. And if you are approaching midlife or if you're in midlife right now, and if you're experiencing it as more of a crisis, this is definitely the episode for you to help you reframe what it means to be in midlife. 

And really why this part of your life is just the beginning of so much goodness to come and so much goodness that you can share in the world. So without further ado, let's get into my conversation with Modern Elder Academy founder and prolific author, Chip Conley.
Chip Conley, thank you so much, man, for coming back on my podcast.

[00:04:51] CC: What a joy. And it was such a joy to hang out in Baja for a week with you this summer. 

[00:04:57] LW: Yeah, Absolutely. And we'll talk about what that was, give it context and everything, but first things first, before I hit record, we were talking about my book journey. Because you have a book that's in the birthing process right now called Learning to Love Midlife.

Is that the, that's the final title, right? Learning to Love Midlife. And I was telling you that I was not, my book Travel Light was not a New York times bestseller and that has to be intentional, but I'm happy that it's a useful, it's a very, I feel like it's very useful. I feel like it's my best book actually. And you were saying that you have had a New York Times bestseller and but you don't think it was really your best work. You've written what seven or eight books. 

[00:05:38] CC: This will be my seventh book. And yeah, I had a book called Emotional Equations come out and it was written, it was like an emotions book for men and did a campaign around it.

And what I mean, a campaign is like I spent some money building a set of bulk purchases by people who are going to have me be speakers speaker at a conference. And so people bought books and then we had a lot of PR and. The book was number seven on the bestsellers list one week and and number 11 the next week.

But the truth is, it was an okay book. It's not a bad book, but it's not the book that people come to me and say Oh my God, that book changed my life. Or if someone says to me, gosh, you got all these books, which is the book I should read. I think it's so true of so many things in life is like the momentary achievement doesn't necessarily speak to the long term meaning. And it's the long term meaning. It's the thing that you've done that is not an accomplishment or an achievement, but it is an extension of who you are in your soul that you feel the most dedicated to. And so for me, in my writing, I can say that there's other books that I look to and I say that is, that was a little window into my soul and into my brain in some cases, that is much more meaningful to me. 

[00:07:06] LW: After having gone through that process, that was book number three of yours? 

[00:07:10] CC: Emotional Equation was number four. 

[00:07:13] LW: Okay. So were you tempted to replicate the same formula for all of your other books, seeing as how you saw, okay, this works, I got on the New York Times, or?

[00:07:22] CC: Here's the thing, once you've been on it, big deal? The aspiration to want it is there, but the moment it's like in your, in the palm of your hand, it's like the hedonic treadmill. You pursue, you pursue. And then you like, get it, like you get the girl, you get the guy you get the sports car, you get the money, the home, whatever the hell it is, and then it diminishes in the palm of your hand. Yes, it is incredibly helpful to me that I can say Chip Conley is a New York Times best selling author. And I only have to have one of those to be able to say that. That's right. So I will say that there, that some of it's gaming the system because it's like I can say that.

But I also realized that it didn't really matter. At the end of the day do people go out and buy the book because it's on the list now? Probably not. Can the second printing of the book say a New York Times bestseller? Yes, and that probably helps. But it's like, everything. The substance is more important than the sizzle.
And so like the substance of the book and your book, Travel Light is the substance is what's essential because that's what lives on into the future. People will forget whether it was a bestseller or not. 

[00:08:34] LW: You're a prolific writer. You have a daily blog, the wisdom well as someone who writes all the time and you've written several books, and I'm asking this from the perspective of the listener who may have an idea, but how do you know it's time for another book? 

[00:08:49] CC: Yeah, good question. Let me start by saying when I was 13, I said to my parents, I want to be a writer when I grow up. And my dad said, Chip, writers are either poor or psychotic, and most are both.

And I had no idea what psychotic, I still don't know what psychotic means. I just don't think it's very good. And so I ran away from writing. I was the vice president of the creative writing magazine in my junior high school. I went to an inner city high school and I passed AP so I didn't have to at college take any English classes. And so I just ran away from it. It was only after I'd been, become a pretty successful entrepreneur. In my late thirties that I started writing again and wrote a book. What I have found is that when I have a book inside of me that is gestating, and that's what I really think of it as, like you're pregnant with an idea, the idea starts to formulate, I start to dream about it, I start to write notes about it.

Now, with a daily blog, Wisdom I will start, when you're doing a daily blog, you end up writing a lot. And I see, like where, what's juicy, where am I going what's coming up, and as that's happening, something's forming inside of me, and If I'm doing it I start to feel like it's not so much forming inside of me.

I am learning how to channel something through me. And that's when it feels great. When I wrote my book, Peak, how great companies get their mojo from Maslow. It's a business book and a psychology book. But I was having dreams about Abe Maslow, the famous psychologist at nighttime, and then going down the rabbit hole trying to understand what did they do later in his life? He died at 62. What was he studying? What was he interested in? And I was like, Oh my God, the things I'm thinking about is like, how do you apply Maslow to business? That's what he was doing later in life. Very few people knew that. And that's when I was like, Oh, I, I'm on the right path. And then I just started channeling it. I channeled that book. I channeled that book, no doubt about it. And many years later, I'm of the mindset okay, how do I create that again? 

Liz Gilbert has a beautiful Ted Talk about this from about 2010. And it's about how genius Is just learning how to tap into the genie. And there's a genie out there and it's that collective consciousness is that it's that ability to channel that through you and the idea of the genie was something that's, that centuries old. 

And I believe that learning how to become the channel the conduit is When I'm at my best with my writing. And so I know that I'm supposed to be doing that writing when I feel pregnant and ready to deliver. And when I deliver that, I better sit down and deliver at the keyboard. 

[00:11:30] LW: Yeah, that's been a recurring theme in your life. And when I was down in Baja, Mexico, where you've started Modern Elder Academy, you talked about the inception of that idea of being a Baja aha, which again is that same idea of intuiting this different direction in your life. And in the book, you talk about your version of the hero's journey that you also dreamt about, or you conceived it from a dream, which I want to unpack later on in the conversation. 

First though, you did a great job in the opening of the book, talking about your backstory, catching people up.

And for the listener, I interviewed this is our second interview with chip. So we originally went deep into his backstory back on episode 125. If you want to go back and listen to that at some point later, just to get a context. But for those of us who don't know, can you just do the same thing that you did in the opening of your book and just catch us up to how you became who you are?

[00:12:25] CC: Yeah. A couple of years out of Stanford Business School. I'll start with that. I started a boutique hotel company. I can go earlier if you want me to, but that's 26 started one of the first boutique hotel companies in the United States. Call it Joie de Vivre. It means joy of life in French. I liked that except for it's a great impractical name for a company because in the United States Don't know how to spell it.
Don't know what it means. Don't know how to pronounce it but it grew for 24 years, created 52 boutique hotels around california each with their own Name of the hotels had their own individual names. And long story short is I loved it till I hated it and in my late 40s, I had some really difficult times.

I lost five friends to suicide, all men, 42 to 52. I had my own suicide ideation. I had a flatline experience where I died and went to the other side. I had a business, this hotel company that was struggling mightily during the Great Recession, and I had a long term relationship ending, and a African American foster son going to prison wrongfully, and like everything that could go wrong was going wrong, and I got through it, and I got to the other side, but I was like, note to self midlife sucks. Midlife, I gotta I'm not sure what the solution for midlife is. 

And then I got into my fifties and um, sold the company at the bottom of the market, but got to the other side and my fifties was my best decade ever. I'm, turning 63 this month and I love, I loved my fifties. I'm still enjoying my sixties too. And my fifties helped me to see I didn't have to be youthful anymore, but I needed to be useful and I ended up being useful at Airbnb 11 years ago when the founders tapped me on the shoulder and said, Hey, we have this little tech startup that's growing quickly, but we don't know what we're doing.

They did know what they're doing for sure, but they didn't have anybody with an entrepreneurship or leadership background or somebody from the hospitality or travel business. And so I joined them and became their modern elder as they called me. Someone who is as what they said, as curious as he was wise, and I like that, like the alchemy, a perfect alchemy of curiosity and wisdom.

And so I joined and spent four years full time there, three and a half years part time. And it was when I was in the part time role that I started writing a book called Wisdom at Work, the Making of a Modern Elder. And I was writing that here in Baja on the beachfront home I have. And I was like, okay. I, my Baha AHA was going for a run on the beach and coming back and having an epiphany and saying, why are there no midlife wisdom schools? Why aren't there a place where people in midlife can reimagine and repurpose themselves, whether it's their personal life or their professional life or their spiritual life, their physical life, whatever it is, how could we help people understand the stage of midlife and what it offers?

So that's how MEA came about, the Modern Elder Academy. We've been doing it now for six years. We have 4,000 alumni from 44 countries. It's been quite a, and we've had the best, you've been a faculty member, we've had Matthew Ricard, the famous Buddhist monk, Michael Franti, a world renowned musician, Dan Buettner, Esther Perel just a lot of famous, Mark Nepo, Mark, Mark Hyman a lot of really great thought leaders have been here, and we have next year with Richard Rohr. Oh my gosh, Pico Iyer just beautiful people who want to be involved in a movement that is helping to elevate the importance of wisdom. 

So as a midlife wisdom school, what we really try to help people with is how do you help people to unlock and then unleash their wisdom at a time where human wisdom is really meant to help balance artificial intelligence. So why not give some additional attention to helping people to understand. How do you own your own wisdom? 

[00:16:10] LW: Speaking of which you mentioned that Airbnb tapped you. I know that's a well known part of your story. One thing I was curious about, though, was because you've taken a sabbatical between working with them and selling your company at the bottom of the market. Why did they tap you? Did you have a connection or? 

[00:16:30] CC: No, so it's a good question. Gosh like in retrospect, I look like such a smart guy. But I didn't reach out to them. They reached out to me. It was a tiny company. I thought their business models sucked. I just this is not a good idea. Who's going to stay in each other's homes? But of course I'm a boomer, and they were millennials, and it was working with millennials, but part of what they needed to do was figure out how to take it mainstream. So they reached out to me because they I was well known in San Francisco. They were based in San Francisco They know they knew I'd sold my company they'd read my book Peak and they loved that book and they said we like we'd like to create a peak company like You define it in that book. So my book helped and they'd heard me give a speech and they'd also been to some of my hotels and some parties I've thrown at my hotels at, boutique hotels are fun places and I'm a social alchemist.

So I know how to mix people. I'm a mixologist of people. And but what they really knew at that point was they needed to find the experts in the different areas that we're going to, that Airbnb needed to figure out, like the expert in policy and regulations. How should Airbnb be regulated? And so they hired a guy named Chris Lahane to do that.

And they hired me to be in charge of hospitality and strategy for the company. And so I was in charge of all the hosts in the world, but long story short is I think more than anything, they hired me for my knowledge, but what they said they got from me after a couple of months was my wisdom. And at that point at age 52, I had never really thought of the difference between knowledge and wisdom.

And. All of a sudden, I'm being told, hey, you're wise. It's oh, okay, let me go to the dictionary and look up the word wisdom or wise and see what that is. And then I realized that since age 28, I had been making notes in a series of diaries, and now Google Docs, about what I'd learned every week. It was really my wisdom book, and it was my at the end of each week, I would spend 20 to 30 minutes saying, here's what I learned this week, and I don't know why I started doing it because I felt like an idiot as a young CEO of a company. And I was trying to make sense of what I'd learned. 

But what I've come to learn over time is oh my gosh, our life lessons, our painful life lessons are the raw material for our future wisdom. So the thing we need to do with these life lessons is we need to metabolize that experience. ' cause if you can actually make sense of the things you're learning personally, professionally, spiritually, physically, if you can do that, you have built pattern recognition that supports you in the future to be able to have a better intuition about making decisions, be more discerning. 

And so I can't say that in, at 52 when they'd said, Chip, you're our modern elder and we hired you for your knowledge and what you gave us was your wisdom. I had been focusing on wisdom for a long time, but I hadn't really given it much, I don't know, much conscious attention other than, yeah, I was trying to make sense of what I'd learned every week. 
So for those of you listening, if you want to actually try to figure out how to accelerate your wisdom, make a practice. It's a wisdom practice of, could be monthly. For me, it was every weekend. That could be quarterly with my leadership team. I do it quarterly with them. I say what we all come together once a quarter and say what was each of our biggest lesson of the quarter and we share it with vulnerability and we learn from each other.

So wisdom is really important because the not the world is full of knowledge. It's that's not scarce. It's all in our iPhone, but what is scarce is wisdom. And what's scarce is what's usually valuable. 

[00:20:03] LW: In the book, you talk about identity and how we can be so attached to that identity, especially when we get into midlife. And you were an entrepreneur, a decades long entrepreneur when you were in your early 50s. And I'm in my 50s, right? I'm in my early 50s right now. So I'm just relating to that story and how the Airbnb experience for seven years off and on was such a pivotal point in you shifting into this new calling of, scaling the idea of the modern elder.

And, but having had the identity of an entrepreneur, was that a difficult choice for you to work with or work for some after having done that being the top guy all those years. 

[00:20:48] CC: Yeah. So for 24 years, I was the CEO. I had 3,500 employees and it's and I was the one who got my face in the paper it was the best and worst of worlds because if things were going badly, it was my fault, particularly well, it was my, my benefit. But I had a lot of ego attached. Let's just be honest. I had a ton of ego attached. I'm a kid who grew up. I was a very closeted, I was a great athlete, I was a good student, and I got along with everybody, but I was a closeted gay person, and it wasn't until I was 22 that I came out, and I'd had a lot of girlfriends during that time, I almost got married at one point or didn't almost get married, I almost, I had a woman who I thought would be my fiancee in college, but all that time I knew. And when I came out at 22, it was like an opening of a door.

And then here I am four years later starting a company and it becomes very successful. So in many ways, the fact that I was proving myself as a gay CEO, meant that I had a lot attached to being that founder and CEO. It had a lot to do with my sense of self esteem. So joining Airbnb and all of a sudden being the mentor to the founders, but also reporting to Brian. The CEO who was 21 years younger than me was. It forced me to rightsize my ego because all of a sudden I'm reporting to someone who's like the age of my theoretical son. And that forced me to be curious. And I had to become a mentor. A mentor, and an intern at the same time. 'cause there were some certain things that I was wise about with Brian, but there were certain things that he was really smart about with me.

And I learned from him as much as he learned from me. But also learning how to not have my name in the paper. My job is to help the founders be successful. 

I believe that in our lives, the, in the first half of our lives, often it's, the I am statements in our head are like, I am my job. I am my things, my stuff. I am what I own. I am what people say about me. I am what I control. I am how I look. I am what gives me pleasure. There's a lot of, I am statements and they're usually very egocentric. But I think after age 50, we start to shift. And for some people, they do this way earlier than I did. But I'm just saying for me, it was my 50s where I started realizing I am what survives me. And actually, even better than that I am how I serve. Or I am ready to serve. And that's where I really feel very attuned today. I was an attainer, and now I'm an attuner. I'm attuning with what's coming through me. I'm attuning with my talents and my gifts. I'm attuning with my desire to serve and be generous. And that feels good. And when you're attuning, you're at one. And when you're attaining, sometimes you have to atone afterwards. Because in the attainment mode, you have sharp elbows. I do. 
And so I'm like, I'm competitive. And so moving from attaining to attuning and there's some sports, certain things. Meditation is an attunement thing. Yoga should be an attunement thing. For some, it's an attainment thing and they like to show off. Surfing is an attunement thing. So learning how to find the things in your life for me, I'll speak for myself, things in my life that helped me to attune and harmonize. It's really valuable because what I get from that is I am one of many and I am here to serve in a way that is beyond whatever I expect in return. 

[00:24:16] LW: Would you say you learned that on the job at Airbnb or did you grasp that during your sabbatical? For people who are entering into their 40s, which is where you identify midlife 40 to 65, how can they facilitate that sort of shift from attaining to attuning? 

[00:24:32] CC: Well, I think it's a great question. I think starting to see how do you move from the ego to the soul? So Richard Rohr and Carl Jung have both said that the primary operating system for the first half of life is the ego. And for the second half of life, it's the soul. And in midlife, there is this operating system change, but no one gives you the operating instructions for this new system. 

So some of the questions to ask oneself during this time could be who am I here to support and serve? And how can I do that? What will survive me? And it doesn't have to be something like building at a college with your name on it. It doesn't even have to be a book that you've written. It could be literally the mentorship you gave to somebody. Who are the people that I most admire later in their life? And what were the qualities about those people that I would like to emulate. And what you'll see is those people often were people in a role of doing something beyond their own ego. 

I would just say, looking at what makes you passionate, another thing that tends to happen is we get very wrapped up in purpose especially in the United States. What's your purpose? It's it's like some possession. And a purpose can be, there can be a big purpose, there can be a small purpose. But the bottom line is you gotta find the verb before you can get the noun. You gotta become purposeful.

And by becoming purposeful, you will find your purpose, the breadcrumbs to your purpose. So how do you become purposeful? You look at what agitates you or excites you. What makes you curious? What's something that you actually love from the past but didn't have time for? And it's in those passionate elements that you find purposefulness, which leads you to purpose. But again, what agitates you or excites you? What makes you curious and what's something maybe from the past? 

We had someone at MEA recently, a litigation attorney and man, she's one of those people who's, she can see that her life was not better by her profession. Her profession had made her hard edged. And so when we were doing some of our exercises, one of the things we asked her is what from childhood do you remember that you loved? What was something that you had passion about? And she talked about making pies with her grandmother. 

By the end of her week at MEA saying, listen, over the next year or two, I'm going to retire from being a litigation attorney because I don't like the person that's making me become, and I'm actually going to go to cooking school, learn to become a pastry chef and create a bakery.
And that's what I'm going to do with my life. And so the purposefulness that she had to go back to from the passion in her teen years is helping her to see what her purpose is now, because actually, if you try to just go to purpose alone, and you say like, what's my purpose? It's almost too big of a question or it gives you purpose performance anxiety. 

[00:27:28] LW: Anyone who spent five minutes around you, Chip comes away thinking, understanding that you have made a purpose out of this idea of rebranding midlife. So I'm going to ask you that question. What is it about midlife that agitated you? And what is it about it that excited you? 

[00:27:44] CC: Well, What agitated me is to lose five friends to suicide in midlife, all men. And to see that they didn't have much in the way of resources in terms of it's not that they didn't have financial resources. Four of the five were actually relatively well off. But three of those five were entrepreneurs and their businesses were going down in the Great Recession, and their sense of who they were was completely defined by their business card. So I guess that there was a part of me that was just agitated by the fact that at midlife the midlife crisis is like some thing that we talk about and laugh about, but, I think midlife is not a crisis. It's a chrysalis. 
A chrysalis is the in between stage of a caterpillar to a butterfly. It's the cocoon that a caterpillar spins in order for it to transform and yeah, a chrysalis or cocoon can be dark and gooey and solitary, but it's actually where the liminal transformation happens, the metamorphosis happens. And that's really what I think midlife is. 
Midlife is a transformational period. And sometimes it requires us to get knocked up the side of the head with something that's unfortunate; bad circumstances, in my case, yeah, having friends commit suicide, having a partner leave me, having my foster son wrongfully going to prison, running out of cash in my company. It all happened at the same time. 

And so there are times I think in midlife when there's so much happening at once that it forces you to get on your knees and say, okay, I surrender the way I've been doing things isn't working. I need help with doing it a new way. And so that's where the transformation happens. Now Would I have been willing to transform my life as fundamentally as I did If I hadn't had all those circumstances, maybe not. But similarly, there's a word middlescence that hasn't gotten a lot of attention. And then there's the word Adolescence that didn't exist until 1904. We now know Adolescents Are teenagers, and we give them a lot of latitude and say, Oh God, he's just an adolescent. And we give adolescents a ton of attention. Career counselors and school and parents and mentors and you name it. Teenagers get some attention. They don't always want the attention But they you know, and i'm and let me be clear here I'm, i'm also talking about often privileged kids get that. Not all kids get that. But who gives the attention and love and support to someone in midlife? middle essence Because when you're going through middlescence, you're going through hormonal, emotional, physical, and identity transitions, just like you're going through the same kinds of transitions when you're a teenager. But we don't really have support.

[00:30:33] CC: systems or schools or tools or rites of passage or rituals. And that's really what, why I created MEA is because I wanted to create something that felt like it was needed. And that I needed it and that my friends needed it. And after 4, 000 alumni coming through the program now, it's Oh my God, my greatest sense of success in my life has nothing to do with money or fame or ego or any of that. It has to do with, as you saw the feeling of like being a midwife for midlife epiphanies, and to be the person at the birth of someone's recognition that they can shift their life in a way that gives them more options, and gives them a new sense of possibility and hope. 

[00:31:19] LW: And so for the listener, again, MEA stands for Modern Elder Academy. It's a platform. It's an ideology and it's also a physical space. It's a really beautiful physical space that I was honored to have the opportunity to come and facilitate with Chip for a week this past summer.

What you all are doing is you're essentially rebranding what it means to be in, in midlife and you have a whole curriculum. So everyone who comes there goes through a similar type of curriculum, where you, look at every aspect of midlife and you talk about. How again, this is a chrysalis. This is not the end of anything. This is actually the beginning of you getting to shift into a place where you're able to use all of the wisdom that you've accumulated over these years in a way that aligns with whatever it is that you feel that you're here to do for this particular season in your life. And it's a, it's such a beautiful space that you have created. And so people walk away from there, myself included, you walk away from there with a whole different mindset around what it means to be in midlife. 

And in your book, you talk about how just shifting your mindset, not that you have to go to the MEA, but just understanding it in a different way can actually grant you additional years. I think you eight years or seven. 

[00:32:40] CC: Seven and a half. Yeah. So Becca Levy at Yale has shown that. When you make a shift from a negative perspective on aging to a positive perspective on aging just that mindset shift, this mindset shift adds seven and a half years to your life, which is, it's, and it's not easy. We live in a very ages society and a lot of our ageism is self imposed. So making that shift you need some tools to help you do that. But that seven and a half years of additional life is more life than if you actually just stopped smoking at age 50 or you started exercising at 50. 
So it's a profound, it can have a huge effect on public health and yet we don't really do much we have lots of anti aging creams and products. We don't have a lot of pro aging creams or products and that's why the subtitle of my book, learning to love midlife is 12 reasons why life gets better with age. Because what I wanted really to do is to help document the things that do get better with age. We're very clear. What doesn't get better with age. Our waistline it might not be as good. Although dude, you're pretty good. You got your videos and you're good you know how to you know how to work it and keep yourself lean. 

But you know you get wrinkles. So there's all these things. Your short term memory is not good not as good as it used to be. But there are a lot of things that get better with age. And I do believe strongly that aging and growing are the same thing But you talk to a 15 year old you haven't seen in two years and say, Oh, my, how you've grown Johnny. If you see a 55 year old, you don't say my, how you've grown because they might think you're talking about your waistline. But the reality is that we have grown. It's just not in the physical way. We've grown emotionally. We've grown spiritually. We've grown relationally. We've grown, frankly, in terms of, our ability to grok big ideas, be wise, think systemically. That gets better with age. Yes, our short term memory gets worse with age, but our crystallized intelligence, which is thinking holistically, systemically being able to four wheel drive of the brain, move from the left brain to right brain, that gets better with age.

And so I wanted to help people see there are things that get better with age, and there's something called the U curve of happiness that shows that, frankly, after a low period between 45 and 50 we get happier with each decade after that, which is surprising because pretty much a lot of people think oh, you hit 50 and it's all downhill from there.

[00:35:08] LW: Yeah, and you also mentioned something that made me laugh how The Sex in the City sequel. the ladies in that sequel are the same age as the ladies in the Golden Girls. 
[00:35:19] CC: Which is so funny because you, it just shows how we've changed it like it just shows that Women in their fifties can be stylish and hip and all that stuff, as opposed to okay, retired and and dreary.

[00:35:33] LW: Let's talk about some practical action steps that people can take to sort of become more present in this midlife stage, so that they can start to share more of their wisdom. And what I'm referring to now is you said that Dan Buechner came in and spoke at a Modern Elder Academy. And in your book, you've listed off some of his tips from the Blue Zone research. So can you just talk a little bit about that? Because I feel like you guys also incorporate some of this into the curriculum as well. 

[00:36:02] CC: We do, We do. Um, So blue zones is research that Dan started many years ago looking at those places in the world that had the largest percentage of centenarians, people who've lived to 100. And he has nine different variables that are common amongst these five places and some of them include things like having a plant based diet, learning how to have a close relational community that you can rely upon, doing exercise. Now, he's very clear about saying that doesn't necessarily mean going to the gym. It just means incorporating physical activity into your life and we do less of that because we sit more. So we think, okay, we just go from sitting to going to the gym and that's fine, but there's all kinds of other things you can do.
One of the things he was able to show is in Okinawa in Japan, which is one of the blue zones places, part of the reason that they do well is because they don't have chairs. They do have chairs, but not many. They basically sit on the floor. And so when they have to get up, they have to get themselves up from the floor, which is easy to do in your twenties or your forties, or maybe even your sixties, but a lot harder to do in your eighties. But if you've been trained to their whole life doing that, it's easy in your eighties. So that's, one thing. I mean, I think it's spiritual minimalism, what you have helped to show is a big part of it. We do something that at MEA called the Great Midlife Edit. And the Great Midlife Edit is at a fire overlooking the ocean people saying, I'm ready to let go of the mindsets, the habits, the identities, the obligations, the people in my life that no longer serve me. And I am ready to let go of that. And in your case, it's the stuff. 

And you know, the first half of your life is about accumulating, and the second half of your life is about editing. .And, if we can realize that, the accumulation had some value, and then you realize that I got all this stuff, whether it's the stuff in my head, or the stuff in my house, it's too much. I do not need this. It's weighing me down. And so if midlife is actually some sociologists say it's from 35 to 75, 40 years long It's a marathon. If you are carrying all of your baggage and stuff on your midlife marathon you are weighted down and you wonder why at age 50 you're exhausted and running on fumes and you need a midlife pit stop. And so learning how to edit and to be a spiritual minimalist is part of it.

So I think you're a beautiful example of it and Light people loved your week. It was a beautiful week. People really resonated with not just the message, but the messenger. And, there's a lot of people out there in the spiritual and self help world who are great messengers, but they're not, I'm sorry.

They're they have great messages. They write great books and they have New York Times bestsellers at whatever. But then you meet them and you realize, oh my God, I've had this person on a pedestal. And there's they're not that interesting or they're awful, or they're just egocentric or narcissistic, or they're boring or whatever it is, and you're not those things. And I think what people saw is, you live by your principles. And I found you to be very curious that week, which is it's really important part of getting older is like staying curious and being open to new experiences. If you don't do that, if you don't do that, your life gets really small.

And one of the questions we like to ask at MEA is 10 years from now, what will you regret if you don't learn it or do it now? Because imagining the regret of 10 years from now of something you don't learn or do now is a form of wisdom because it's anticipated regret. And anticipated regret can be a catalyst and we sometimes need a catalyst in midlife because we sort of get into our habits and are just the momentum of our life, the inertia and all and we realize that we're sort of bored. And we don't know how to break out of it. And that's, that's exactly, we get stuck, and that's when we need friends to help us get unstuck, and and MEA gets, has a lot of people who end up here partly because they're like, I'm stuck, I don't like my relationship, my job, my relationship to my kids, my sense of spirituality, none of it's working And I'm stuck and I don't know how to actually unstick it. And helping people to unstick it is key because otherwise you get calcified.

And part of the challenge we have in the United States today is with the older population is. We have a lot of people who are calcified, who just got their lives more and more narrow, and their politics and their perspective on life became, match that. So I don't want to be that.

[00:40:56] LW: Yeah. And as a result, there's a lot of loneliness being experienced, especially with men. And I just want to make another observation about that week I spent. There was a group, a cohort there I believe it was nearly 30 people, men and women. And and there was like a group name and everyone was super connected the whole week. And then there, I guess there was a WhatsApp group that was formed from that. And I've heard from a few of those participants and they're still in touch. And it's a great way. If you don't have a big community, because one of the things that Dan talks about in his Blue Zone framework is, you want to prioritize loved ones and you want to find a healthy tribe.

And it's, and you said in the book, it's not that you should, you need to have healthy tribe in order to cultivate this sense of purpose and presence. 

[00:41:46] CC: There's a Harvard study that's been going on for 85 years, and Dr. Bob Waldinger has been running it the last few years. And they've studied the same group of people for 85 years. Now, obviously most of 'em are dead now, but there's still some of them around and they're, there's centenarians and the what he was able to show in his book, the Good Life, which came out earlier this year was the number one variable for people who are happy and healthy in their eighties was how invested were they in their social relations in their fifties. And so investing it's, it's not just a feel good thing. It's going to help you live longer and be happier and healthier. Now, for those of you saying this all sounds well and good, but I can't afford this. You got a couple alternatives. We have financial aid very, over half the people who've come to our Baja campus have been on financial aid. That's really important. And number two is we have online courses. And those are a lot more affordable. So there's lots of ways for people to do that.

But once you're actually an alumni, one of the 4, 000 alumni we have around the world, you're part of a regional chapter. Your cohort keeps getting together. Yeah, we have reunions. And it is a community. And there is a deep sense that, wow, I am part of something that almost feels like a small movement that's just sort of growing and uh, it's beautiful. 
[00:43:06] LW: What are some other best practices that you've heard about just from the work that you do, especially for guys older men to cultivate more of a sense of community, guys who don't really have any friendships or. 

[00:43:19] CC: And it's much truer for men about not having friendships. Um, well, Let's start with just saying who in your life are you, do you feel like you'd like to become closer to. If the answer is no one, then who in your past life; high school, college, early career, is somebody that you really enjoyed, but you haven't stayed in touch with. And, how might you reach out to that person, or those people, and just say, Hey, I would love to have a meal with you. Or, if you don't live in the same city, I would love to just do a Zoom call with you and maybe once a month, we just catch up. 

You have to have a little courage and vulnerability to be willing to do that because someone might not even respond to, but I got to tell you, if you try it three times, at least one of those three people is probably going to respond and maybe all three will respond. And then you start to build a friendship. The process of building a friendship doesn't mean you go to like, very vulnerable questions overnight. But it does mean you start to actually say, you know what? I am to a stage in my life where I am more open to being open and I don't want to be quite as guarded. You know, I'm open to having a conversation with my best college friend who I haven't seen in 25 years but he actually lives 50 miles away from me and I'm gonna get together with him. And when I have dinner with him I'm gonna talk about the fact that my marriage isn't all that good right now. I'm an empty nester The kids are gone, and my wife and I have grown apart. And I want to talk about it, and I don't necessarily want to go to therapy. And that is, that, you have it available to you. There's no cost in doing that other than driving the 50 miles to see your friend. But there's beauty in it, potentially, and there's really the opportunity to reciprocate. Because, just because you feel lonely and feel a little lost and feel like you can't talk about these things doesn't mean like the rest of the world is feeling like they can do it. The fact that you reached out to that person means that, guess what, he probably, or she, but let's say it's a he, another man, he probably needs this too.

So I love it. You know, We just had a I just taught two weeks in a row here in Baja, and we're going to be opening in Santa Fe, New Mexico, with our first campus in the U. S. In March and this last week we had as many men as women. It was a full even mix. It was so beautiful to see the men to see them just realized opening up like and actually, I think the men and these were like there's one guy, he's a professional football player, and he had a hard time with identity. What do you do when you've spent, since age 12, living the life of an athlete who becomes famous, who goes into the NFL, and then, in mid 30s leaves, and then for five years is lost, has some drug addiction, etc.

He at 40 is early midlife, but he was really far along on his midlife because he was pretty much not in a good place. So how do you open up? That guy was crying. He said he hadn't cried since he was 12 when his father passed away. Having people being able to witness each other, learning, meeting people and getting to know them from the inside out is really critical.
Dacher Keltner is one of our faculty members. He's a UC Berkeley professor who started the Greater Good Science Center. And he wrote a book called Awe. He's the world's leading expert on awe. And he was able to show the eight primary reasons that people find awe in their life. And of course, I thought number one on the list would be nature, but it was number three on the list. But number one and number two on the list are exactly what MEA is about. 
Number one on the list is moral beauty. When you experience moral beauty, you see courage and kindness in other people. And in seeing that, it gives you a sense of trust and love of humanity. Number two on the list, and we see a lot of moral beauty, as Light in, in our weeks.
The second is collective effervescence. That is when you're in an environment where people's sense of ego separation evaporates, and what comes into its place is a sense of communal joy. Now, I was a founding board member of Burning Man, the Burning Man non profit, and I know what collective effervescence is based upon what happens on the playa, but I also know what happens in, with 20 or 30 people in a workshop.

When your sense of the judgment towards yourself and others, the sense of separation starts to melt and there's a gooey, beautiful feeling of Oh wow, I feel a sense of connection. As I'm an enlightened witness of someone else and they're an enlightened witness of me. And what a beautiful experience that can be.

And what a rare experience that is. And yeah, so that was a ramble. Sorry. No, it's great. 

[00:48:11] LW: And I also want to offer a personal experience of mine. During the pandemic, I had a friend reach out to me and just say, Hey, do you want to be a part of a men's group that I'm starting? And there was only three of us. And we said yes. And we started meeting like every month and then we added more people, and I got so inspired by just having, because I didn't have an outlet to just talk about things in my life. So I reached out to my three brothers and I said, Hey, do you guys want to start a men's group? And they said yes.

And what I learned from that experience is that they're going to take the cue of how vulnerable or how collectively effervescent to become from you from the person who's actually initiating the idea. Yeah, it's a very simple framework that you could do if this sounds exciting to you, it's just this thing called rose, bud, thorn where everybody goes around and they talk about what is going well in their life, what's rosie, what they're looking forward to, what's budding, and then what is challenging them. What's a thorn? And everybody can spend 10 minutes just talking about that. And you go first and you share openly and as, as transparently as you can, and that's going to set the tone for everyone else. And so while you're waiting to go down to Baja, that could be an alternative way of cultivating some community. And you could do this obviously over Zoom and long distance, or you can do it in person. Love it.

What's a blah zone? 

[00:49:35] CC: Blah zone is when someone is it's not a blue zone. A blah zone is when someone is so deep in their comfort that they're bored silly. They have lost a sense of vitality in all forms; spiritually, emotionally, physically, mentally, relationally, and I think a lot of people in midlife are in the blah zone. And it's often because they've just they've been doing the same thing over and over again.

[00:49:59] LW: That's like the caterpillar phase as you're moving towards the chrysalis. 

[00:50:03] CC: Yeah, it's like the, it's the caterpillar, what happens with the caterpillar is it eats and eats, it consumes and produces, it's it's going and going and going and going, and then, and that's sometimes what we're doing in life, but because our lives often in our 20s, 30s, and 40s are so busy, you have to sort of be efficient, especially if you have kids, be efficient about how you operate your life. And so therefore there's not a lot of room for curiosity or for yourself. And so you're sort of like, okay, you're on the treadmill. And you wonder why at 50 you're both worn out and bored, and in a place of a lack of inspiration. 

[00:50:41] LW: Cynical, a bit jaded. 

[00:50:43] CC: Yeah. Yeah. Yeah. And just, and definitely not inspired. And inspired, as you know, inspired means to breathe in. And so learning how to just take a deep breath and say, you know what, I am in a prison of my own making. And once you've seen that, as Shakespeare said, there's nothing worse than the person who is in a prison of their own making that they don't know that they've created. That is, it's not, that's a paraphrasing, but that's exactly how a lot of people live their lives. And that's why spiritual minimalism and the idea of going light and learning like, okay, I am going to pack up my prison and send it away. And I am going to not have that prison anymore. And whether that prison is the four different storage units, I have of all the stuff that can't fit in my garage, the prison is the fact I'm on, as I was at one point in San Francisco on five or six different boards, all of which were quite worthy and not, they're all nonprofits that I cared about, but it was like, Oh, my God. It was, I was bored silly and I was, because I was sitting in board meetings all the time and I wanted to give back, but I also didn't want to, I didn't want to have my life so structured. 

[00:52:01] LW: You know, a smaller way you could do this to shake things up is, could learn how to surf in your fifties, or you could learn a different language or do something that, that stretches your brain or that stretches your body a bit. And you've had some personal experience with that as well.

[00:52:16] CC: Yeah. Yeah. At 57, I started learning how to surf because I, in Baja, we're near a surf break. That's just just one beach over from us. And I decided to learn Spanish because I learned French in high school and I'm living in Mexico. Again, back to that question of I asked myself, 10 years from now, will it be easier to learn Spanish or easier to learn to surf? And the answer was no. It gave me a seize the day incentive to say, I'm going to try learning it now. And I did. And that's what we need more. 

The reason why learning something and becoming a beginner again is valuable, and we should always have something in our life in which we are a beginner, is it humbles us. And it helps us to see that we can learn something new in the synapses in our brains can actually get stimulated. It helps us to be open to new experiences. And if we're open to new experiences, we're also open to new people. And so there's so much value in it. And yet no one in midlife says I want to go to beginner's school.

I'll never forget a few years ago for my birthday, my friends took me to circus school and we all went to circus school and that was like the ultimate beginner school because like, oh my god I'm going on the trapeze and like you're doing all these things that you just don't know how to do and at first I was like I can't do this because I'm not gonna be good at it. And then the key in life is to learn how to take it easy and have a sense of humor about it and say I don't care. I'm going to have fun. 

And that's how I, that's how I surf now. Cause at first when I was out there surfing and learning, there were a lot of people I know it out there surfing with me. And they're like, I'm terrible. They're good. It's like going to a yoga class. That was my thing about social comparison in yoga class like oh, I hate yoga. I love meditation because I close my eyes. I'm not comparing. Yoga I am comparing and so I realized okay my way to get over that was to do one on one yoga classes with Teddy our yoga teacher. 

But the bottom line in all of this is you we gotta learn how to take ourselves less seriously, not to personalize what other people say about us, or what we think that they think of us, because they're really not thinking about us. And see, as Helen Keller said, life is either a daring adventure or nothing at all. And this is comes from a one woman who was both deaf and blind. So yeah, if Helen Keller as a deaf/blind person can say that life is a daring adventure, then I can as too. I can do the same.

[00:54:50] LW: And when you get beyond that mental block, you start to experience more age fluidity. Talk a little bit about that. What is, what do you mean by... 

[00:54:58] CC: Dude has read the book? Um, So we know what gender fluid is and it's a, sometimes controversial, but like overall, I think very clear. It's like Kinsey said that we were gender Kinsey, like the famous psychologist said that people are on from a one or zero to six on the Kinsey scale of their sexuality. So gender fluidity is clear. Age fluidity is not clear. If you want to make someone feel good as an older person, you could say that they look ageless, but then that's suggesting that age is a bad thing. If you're ageless, it means Oh, you're not showing your age. I like age fluid and age fluid means I am all of the ages I've ever been and will ever be. And I'm not defined by a generation or by my age because there are times when I'll be you know, silly 14 year old teenage boy with my adolescent humor. And then there'll be other times, which is a lot of the time and then there'll be other times when I'm the wise elder amongst a bunch of younger people. And I have some, some discerning wisdom, maybe that to offer. So being age fluid means that you're just not, you're not confined. And gender fluid is also not being confined. And so why not have age fluid, fluidity? Now, if, as I say in the book in learning to love midlife, when I first, I thought, Oh, that's a great term. And then I went on Google and said, age fluid. And it's Oh, it's someone who's a pedophile who thinks that they can date anybody at any age. Like, oh no, that is not the age fluid I'm talking about. I'm talking about a different age fluid.

[00:56:36] LW: And so yeah, you got some awesome terms in the book. You got transitional quotient that your TQ where you can tell where you are on that spectrum of going from a caterpillar to a butterfly. How does one know when they're arriving in butterfly stage? 

[00:56:52] CC: You know when you're arriving in butterfly stage, when the messy middle, so there's three stages to a transition.

There's the ending of something, there's the messy middle, and then there's the beginning of something new. When you're at the, that beginning stage and you've gone through the messy middle, when you're starting to build some confidence in your ability to flap your wings and fly in this new role that you're in.

For me at Airbnb, I had to go through these, this okay, I'm transitioning out of the egocentric CEO. I'm in this messy middle of okay, I am both the mentor and intern. And it was really, I think maybe six months or a year into being at Airbnb that I realized I was no longer in the messy middle because I felt really comfortable in this new era of being a mentor and an intern at the same time. I didn't feel awkward. I didn't feel self conscious. I felt Hey, I'm learning something here. I'm improving at this. And that's when you are at the beginning of something new. 

We talk a lot about this. And if you go to the MEA website, you can get the ebook. It's a brief ebook called The Anatomy of a Transition. It's all free. And you can learn about how do you understand your transitions in a way that allows you to understand what are the tools that help you through each of those three stages, ending messy, middle and beginning. 

[00:58:12] LW: And I mentioned earlier your hero's journey. I feel like it ties into this a little bit. How is Chip's hero's journey different from Joseph Campbell's... 

[00:58:21] CC: hero's journey? So the hero's journey is this idea and Joseph Campbell popularized that it has three stages to it. The ending from a, from Campbell's perspective, the ending of your normal life that you've been living and the call to adventure takes you into that messy middle and then you come back into society beginning with a whole new perspective.
So for me, what I plotted this out and there's a chapter in the book that's about I understand how my story serves me which is another way of saying I understand myself and my life journey and that's important. 

When someone can understand their life journey They understand the through line and the theme of their life and why they're here on earth And as someone said long ago, I think it might have been Mark Twain there's two most important days in your life the day you were born and the day you figured out why. And so figuring out why is part of that through line. So for me, I had to see like, okay uh, for those who want to learn more about this, it's in the book learning to love them in life, but I had to see okay, there's a sort of a similar pattern I have that takes me from being like having a conduit with lots of ideas to feeling a calling around it, feeling passionate around it, then sacrificing and going into being on one dimensional and treadmill and then being the hero and then feeling worn out and then feeling resentful because no one else is keeping up with me and I'm doing it all and then feeling like, Oh, I got to like renew myself, get a massage or do some yoga and then starting to get curious again and then back to that top of the circle where I'm like a conduit again. 

And when I could see that pattern, it helped me to disrupt. Some of the steps that got me there, and I would say that for me, the steps often are, I get so passionate and purposeful about what I'm going to do, I put blinders on, I feel like I need to go do it on my own, and my two co founders have noticed this in me, and they remind me of the famous African proverb: If you want to go fast, go alone, if you want to go far, go together. And so that's, that's written on my bathroom wall. If I want to go fast, go alone. If I want to go far, go together. And I'm good at going fast alone. I am less experienced at going far together. And so I've had to retrain myself because if I'm going far together, I'm less likely to get resentful and also I'm less likely to burn myself out. And I'm also less likely to be egocentric, thinking Oh, I'm the hero who's going to make all this happen. There you go. You're my psychologist. 

[01:00:57] LW: I feel like also in order to create the space to do that, to go far with others, it really helps to have very well defined values for yourself. And you mentioned this idea of the 10 commandments. We don't have to really get into it too deep, but it ties into this idea of editing as you get older and just really honing in on okay, what's most important to me right now that I don't want to sacrifice for this goal, whatever the goal is. And it may seem restrictive, but it actually is liberating is freeing you. Because you're not going to debate whether you're going to sacrifice your family for this goal, or you're going to sacrifice your health for this goal, or you're going to neglect something that is important to you for this goal.

So talk a little bit about creating your 10 commandments. What do you mean by it? 

[01:01:50] CC: I said the Ten Commandments is something I grew up with that I didn't necessarily believe in. And so I created my Ten Commitments. Ten Commitments. And my Ten Commitments of, like, how I live my life. And I review them, once a quarter, once a season, to see, am I on path? Those are sort of my values. I actually, I have a copy of... 

[01:02:10] LW: I was going to say, do you know them by heart?
[01:02:11] CC: I definitely don't, I have to remind myself, some of my 10 commitments. I commit to living a life more focused on my eventual eulogy than my current resume. 
I show up with a passionate engagement in life because that way people will notice my energy more than my wrinkles.

I assume best intentions in people unless they've proven untrustworthy. I follow the old adage, live as if you were going to die tomorrow, learn as if you were going to live forever. 
Number five is I try to be curious, not judgmental. Thank you, Ted Lasso. 
Number six, I seek noble experiments that will help me discover something new.
Number seven, I learn from my mistakes because that's how I grow my wisdom. 
Number eight, I embrace my emotions as they're my best evidence that I'm human. 
Number nine is I don't chase happiness. I practice gratitude and happiness is the natural result. 
And number 10, I remember that my most valuable sense is my sense of humor, as it's something that I will still possess even if I've lost everything else.

So those are, I like them, having read them again. I like them because they're a reminder of what's important to me. There's lots of exercises out there on values like, okay, my family's valuable. My spirituality is valuable. But, yes, those things are valuable, but I actually want some, I want more of like of a roadmap with some guidance about what I do and I don't do, because this list of 10 commitments, not 10 commandments, are the things I will do and not do whereas most values exercises are really focused on what's important to you, which is important, it's an important thing, but it doesn't necessarily say here's now that it's important to you, here's how you'll operate and make it practical. 

[01:03:56] LW: And so if anybody wants to really study this framework, obviously they can get your book. I would say if you have the means to step away from your life for seven days, you guys do five day experiences. 

[01:04:09] CC: Yeah, we're doing more and more five days. So you were, we did a seven day with you, but you'll see mostly it's five days moving forward. You can do that. You could do online. But here's the number one thing that doesn't cost you a dime. Subscribe to my blog. It's free. You can find it on the MEA website, It's a great way to understand the ethos and the perspective that I have, and that MEA has around midlife and life in general. It's sort of really the focus on the art of living. And I'd say that's the best way for someone to really understand what's going on. We also post, my daily blog on LinkedIn and, you know, Facebook and Twitter or whatever that's called these days.

[01:04:48] LW: What's the vision? You have a campus in Santa Fe that just opened or there will be opening…

[01:04:53] CC: Yeah. Yeah. What's the long term vision is that a long life learning. So lifelong learning, we know about long life learning is how to live a life that's as deep and meaningful as it is long. That becomes a thing and that we are the pioneer of it. And there are a lot of midlife wisdom schools that open around the world and because we were a catalyst. And I don't expect to open all those. I hope that we are a guide for others to see that this is a thing. 

[01:05:23] LW: Well, Man, it was a wonderful pleasure having you back onto the podcast again. We did a very deep dive into Chip's backstory in episode 125. So definitely check that out next. If you want to learn more about how Chip became Chip and how he developed this framework. And definitely want to pick up a copy of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age which should be out by the time this episode airs. And also if it's not pre purchase the book, that always helps.

[01:05:56] CC: Definitely. Thank you, my friend. It's I'm excited to teach with you again. And just, I really appreciate, as I said earlier, it's not just your message. It's you are the messenger, you walk your talk and I deeply appreciate that. 

[01:06:09] LW: Yeah. If you want to get a double dose of me and Chip, check out the modern elder academy website and just search my name and you'll see when I'm going to be there next. And then you'll get to experience both of us together. Yep. Thanks 

[01:06:21] CC: Beautiful. 

[01:06:22] LW: Thank you for tuning into my interview with Chip Conley. Again the book is Learning to Love Midlife. And you can follow Chip on the socials @ChipConley, which is spelled C O N L E Y. That's how you spell Conley. 

I also recommend checking out his blog, which is called Wisdom well. Chip is a prolific writer. He is super insightful. He's got so much goodness to share. And so subscribing to his blog will bring a lot of that wisdom into your inbox. 

And of course, I'll put links to everything that chip and I discussed in the show notes, which you can find at And if you enjoyed our conversation and you found it inspiring and impactful and you're thinking to yourself, wow, I'd love to hear light interview someone like dot dot dot. Send me a guest recommendation. My email is I love getting recommendations. 

And also if you're going to send a recommendation, please do me a favor and go and leave a rating and/or review for this podcast. And that's because when I reach out to your recommendation, they may or may not have a gatekeeper. And usually those gatekeepers are trained to go to the Apple podcast page for my show and look at how many ratings and how many reviews does he have? And that's how they're going to determine whether or not they say yes or no. If a show has a lot of ratings and reviews, they see that it's an engaged audience and "Oh, my client who I'm gatekeeping for would be able to spread their message to a lot of people by coming on to Light's show. So that's why you always hear podcast hosts like me saying, please rate and review the show. Please review it. Please rate it. It's because that one little tiny thing that doesn't cost you anything. It only takes 10 seconds, has a massive impact in who says yes and who says no when it comes to bringing bigger guests onto the show. 

So all you do is you go to your device, click on the name of the show, scroll down past those first few episodes, you'll see a space with five blank stars, you can leave a five star rating there. And if you want to go the extra mile, leave a review, that would be awesome. 
Also, don't forget, you can watch these interviews on my YouTube channel. If you just search Light Watkins podcast on YouTube, you'll see the entire playlist. And don't forget to subscribe there as well. 

If you didn't already know, I also post the raw, unedited version of every podcast in my Happiness Insiders community a day early. So if you're the type who likes to hear all the mistakes and the false starts and the chit chat in the beginning and the end of the episodes, you can listen to all of that by joining my online community at And not only are you going to have access to the unedited versions of the podcast, but you'll also get access to multiple challenges and masterclasses for becoming the best version of you. 
Alright. I look forward to hopefully seeing you back here next week with another story about someone just like me, just like you taking that leap of faith in the direction of their purpose.
And until then, keep trusting your intuition, keep following your heart, keep taking those leaps of faith. And if no one's told you recently that they believe in you, I believe in you. I believe in you. So you got me in your corner. Alright. Thank you so much. Have a great day. See you next week. 


Love Midlife, Embrace Transformation
Writing Success in Book Publishing
Midlife Challenges and Wisdom at Work
Finding Purpose in Mid-Life Transformation
Positive Aging and Midlife Support
Cultivating Community and Well-Being in Midlife
Finding Inspiration and Growth in Midlife
Understanding Transitions and Personal Values
Taking Leaps of Faith