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January 25th: Trusting Your Gut Instinct with Chip Conley

Intro: When you're in a vulnerable state, you get clear on what's important to you. And when you're getting clear on what's important to you, you are moving on a path on a trajectory toward fulfillment.

Nik Tarascio

So today I'm going to be interviewing someone who is the person that super successful people go to win. They're trying to figure out what to do next. Again, they've achieved their external successes. They've kind of figured out who they are, but then they're asking the question, what do I do now? What do I do on the back half of my life so really excited for this one hope you enjoyed as well.

Welcome to the dream beyond. I'm your host, Nik Tarascio. I'm a CEO musician, an overall seeker of Truth, inspiration, and simply put, how to live the most fulfilling life possible. Growing up surrounded by extremely wealthy and successful people gave me unique and unfiltered perspectives of those who have seemingly made it on the dream beyond we're letting you in on what it really takes to achieve your dreams. What happens when it turns out your destination isn't the promised land you are expecting? And how to process the lessons from your past while mapping of course to true fulfillment. Let's get started.

He is the New York Times best selling author wrote three books so far I'm sure there's more to come. We've got peak emotional equations and wisdom at work, to time disruptive, the hospitality industry at 26. Man, you're making me feel like I have more success I need to pull through at my young age of 42. But at 26 found a job Aviv, which turned into the second largest boutique hotel brand in America. He was Airbnbs, Head of Global Hospitality and strategy. And in 2018, he founded modern elder Academy, the world's first midlife wisdom school, which I'm so intrigued by ultimately gonna be signing up for that this year. 2020. Yeah, a good year for me. And so many other accomplishments, but really wanted to kind of dive right into the question of, what was that first moment when you felt like you made it? And you felt like I'm a success? Sure.

Chip Conley

So Nik, it's great to be with you. Thank you for inviting me to join you on the show.

You know, I think you're starting a boutique hotel company at age 26. I felt like a success, even though I think all of my friends from Stanford Business School, were looking at me like, What the hell are you doing? And I got to felt like a success because I was I really was taking a path that was unusual. I graduated from business school when I was 23, which is really unusual. I went straight through undergraduate to business school at Stanford. And I knew I wanted to be in the commercial real estate business, went to work for a developer for a couple of years out of business school, and then said, I won't do this on my own.

And so I guess my biggest success was just the idea that I'm a Stanford Business School grad, three years out of business school, and I'm paying myself $2,000 a month. So a clearly money was not my primary, my primary objective in terms of my career, and what I really wanted to do, and I bought an old paid by the motel tenure line of San Francisco, a tough neighborhood, and turned it into a rock and roll hotel that became sort of legendary. And I guess I would just say that that era, you know, in my early, early entrepreneurial days, was it was a time when I felt a real sense of accomplishment, because there was no path for me, that said, Oh, Chip, follow this path, and you'll be successful. I was absolutely pioneering a path on this one. And at the end of the day, it served me well, because it helped me to understand my gut instincts at a very young age.

Nik Tarascio

When did you really get in touch with those gut instincts? Was that something that was innate to you? Or was it something was cultivated?

Chip Conley

I think it's a combination of things that, you know, you sort of trust those as you grow up. But I will tell you that practice that really, you know, has served me for 34 years now, when I was 28. So my company was my boutique hotel company was just two years old. We had a big downturn in San Francisco for because of an earthquake. And, man, I had no idea how we were going to fill rooms or how is it going to make payroll, etc.

And so I took a journal off the shelf in my bedroom that I had never written and somebody gave it to me, and I never, you know, I never created a diary out of it. And I wrote on the cover of my my wisdom book. And I started a practice whereby every weekend, I would sit down for 20 minutes to make a series of bullet points, maybe four, maybe six, maybe a bullet points of what I'd learned that week. So it wasn't my emotional experience. It was more like my wisdom experience, my metabolized experience, my lessons I learned.

And I want to say that that process of creating a practice around making sense of what I learned, helped me to develop not just a sense of the metabolized experience that could be also known as wisdom, but also helped me to understand my gut instincts. And I still do this 34 years later. And I do believe that one of the most important things was valuable things we can do in our lives, is to accelerate our wisdom by cultivating and harvesting it quite practically and actively. And that's really what I teach people today. Be I teach them a lot more than that. And that's one of the practices that we teach at our midlife wisdom school at called MBA, modern elder Academy.

Nik Tarascio

So it's interesting is when you talk about your definition of success, it doesn't sound like it was the external trappings that I think a lot of people pursue at a young age, which is partly why I'm curious about that, that gut instinct is what steered you to something that was beyond the I want to be rich, I want to have a plane, I want to have this impact. Like I'm when I say impact, I mean more an audience, I want to have people that look up to me, whatever that was.

Chip Conley

Well, I will say that, you know, when it comes to fame, and power, and money, and I'm gonna status and stuff, the thing that was head over heels, most important to me out of all of those was faith. I'll admit it, I so it I loved when I was, you know, three years after I started my company, I was in People Magazine, they did a story because my rock and roll hotel had become famous, a place called the Phoenix in San Francisco. And, and so I loved that.

And I will tell you that that it was a slippery slope for me, as I learned that I got a lot of self worth out of having my name in the paper or having articles written or, you know, etc, etc. And it was a great lesson along the way as well that you know, a business like the hotel business is extremely cyclical, and you're gonna have your good, good, good years and your bad years. And there's a huge variance between a good a year and a bad year. And I had the Miller you realize along the way that my sense of self worth cannot be attached to the emotional emotional roller coaster, and the hotel industry in California, because all 52 of our boutique hotels are in California. And that lesson was well earned. And bait, it took me 20 years to get there.

But yes, I in terms of the other trappings. I've never been somebody who really cared a lot about, you know, yes, I do. I have a net. Net jet sky now. I mean, I actually do that thing. i Oh, my God, I just totally got you upset. So and so I do, I do enjoy that for the convenience for sure. But how you know, I mean, I have beautiful homes. So I had gotten to a place where I didn't care a lot about money. And as a result, frankly, money ultimately later in my career came to me in the bucket falls. But I will say early in my career, I didn't care about money. I grew a big, big business. But all the money I made, I poured back into the business, which is also not the smartest thing to do.

Nik Tarascio

So I too interesting enough think that fame is on the top of what I was after, as a musician. I just wanted people to look at me and sing my songs back at me. And I'm glad I didn't end up in that position because I think it would have destroyed my self worth in my 20s. How did you navigate it in your 20s? Was it actually a dark time at points?

Chip Conley

It was, I think the part I had to really get clear on and luckily, I've always been fascinated by psychology. And you know, my books have a psychology psychology component to them. So I can see that my personality type was one that had to be really cautious about portraying success, and showing up as unsuccessful. And for me, it didn't mean the suits I wore that car drove it was more like, you know, hey, look at all the things I've been able to build and create as a business. And here are the articles I've written. And here's the TED Talk and given and here's the thought leadership that really helps create a foundation for how people see me.

I think what I had to see over time was that if I really let that go as extreme as it could have gotten, that I would be insufferable to people I was working with. Because it would be you know, Nocturne talked about politicians, specific ones, but we know politicians are just celebrities for whom the whole world revolves around them, and they may put on a good face to you You know, what they say on a night, late night TV show or something like that as a guest, that the fact is the people around them just, you know, find them with impossible.

And so one of the things I really did in my 30s was I did very frequent 360 degree surveys, asking people anonymously, what it's like to work with me. And that was helpful for me, because it allowed me to put my ego in check to think of myself as a work in progress, which is, I think one of the most important things you need to do at any age. And yeah, it reeled me back from getting a little too ego fed.

Nik Tarascio

Is there a comment that you still remember that you had to experience during the 360? That was pretty humbling.

Chip Conley

Well, actually, there's a comment or applet by attaching my my sense of self worth to my business. I said to my good friend, Vanda one day, she says, Well, how you doing? So he? And she, so I said back to I said, well, the Phoenix is doing great. And she said, Well, I didn't ask you how your hotels doing, ask you how you're doing. I was like, oh, like, Oh, my sense of self worth was attached to that. So that was that. And in terms of the feedback, I would say the feedback was sort of hard to hear was that I was not as encouraging of a leader as I thought I was. And I think that that's true, I think the closer you are in an organization to me, if you're if you're the housekeeping staff, or the bartenders, everybody loves chip. But the closer you are, you know, you've seen senior levels of the organization, you see that I am a hard driving guy, I drive myself in a very hard way. And so the closer you are to meet and more, you'll feel a little bit of that.

Nik Tarascio

The I think that's, unfortunately relatable for me, and a lot of the people I think in those in those circles, and I care so much, unfortunately, still care very much what people think about me. So it is hard to everyday have people go, man, what are you doing? What's that move about? So I very much relate to that. Which, interestingly, kind of brings to the question of vulnerability as a leader. And I imagine that you're especially an MBA, you're bringing in people that have been masters of their universe for some substantial part of their life. And now finding like I have to step into a new context, not knowing where to go or what to do. How do you find that vulnerability and fulfillment relate to each other?

Chip Conley

Let me tell you a quick story on that. When I was 22 years into running my company, we had 3500 employees, 52, boutique hotels, and the great recession was in full swing, and we were gonna get hit hard by this recession. I had a flatline experience, I died, I went to the other side, you know, and I came back nine times in 90 minutes because an allergic reaction to an antibiotic. I had a book in my late my backpack that was staying for a couple days in hospital while they're trying to figure out what was wrong with me as Man's Search for Meaning. Viktor Frankl is famous book about passive living in a concentration camp. And I distill down, you know, that famous book on meaning to an equation, which was despair, equals suffering minus meaning. And what I took from that is that meaning and despair are inversely proportional.

So when I went back to my company, and I, and we went into the fall of 2008, and it was a really tragic, tragic time, everybody was really scared about it. I did an offset retreat with our 75, senior leaders in the company. And I went up on stage and I wrote to spirit was suffering minus meaning. And I said, you know, most of you don't know that I flatlined two months ago. Because we wanted to keep it quiet. I want to tell you what happened. And I want to tell you that I learned from this that the most important thing I can do in this company is to be a vulnerable, visionary. And I can tell you, what I felt, you know, how I was struggling with the business before I had the flatline experience, and then a half, you know, divine intervention in the flatline, and I really told my story about the meaning I've been taking since having a flatline experience and man, and what I saw in the room was everybody had been holding their breath.

And all of a sudden, I look there, crying, telling my story, and I'm not someone who's easily cries. And everybody just was so welcoming the idea that the leader of this company, the founder and CEO, that icon, was able to be vulnerable enough to talk about his own troubles and, and really helped remind everybody that man as a company, we need to find meaning as a group, not just as individuals. How do we go to maybe what will be the hardest downturn of our professional careers moving forward. And what are we going to learn from it? Because what we're gonna learn from it, is the meaning.

And so what I got from that was just, you know, just enormous love and praise and people feeling like they can be vulnerable as well. So I guess to answer your question, a vulnerability, one of the beautiful things that allows us to do is just be real and to, to be sort of real about how we're feeling, and how what's important to us. And so to me, fulfillment speaks a lot to what what is important to us. And it is, when you're in a vulnerable state, you get clear on what's important to you. And when you're getting clear on what's important to you, you are moving on a path on a trajectory toward fulfillment.

Because if you can be on a trajectory toward success, but it might not be fulfillment, because it is someone else's definition of success. It is, you know, the classic thing that social scientists talk to talk about is the hedonic treadmill. And that is when you are running for something, you're going to actually go out and try to get it and once you get it, it's you turn up the speed a little bit further, because it is worth as much once you've actually gotten it in the palm of your hand. So fulfillment is a very personal endeavor. And the more you can get clear on what your own personal form of performance is, the less likely you will be our mat hedonic treadmill of constantly comparing yourself to others.

Nik Tarascio

How do you find that line, and maybe this is a flaw in my own thinking of, I want to be vulnerable, I want to be open, I want to expose myself to my team so that they know who I am, or whoever it is that I'm trying to influence or connect with. But is there a line where someone has opened up too much, and the confidence wanes,

Chip Conley

So vulnerable? Visionary, I like the alliteration of it. Someone called me that, and what they said to me, and I think they, this captures what you're asking for this chip, we deeply appreciate your vulnerability because in in your vulnerability, we understand you're a human, we you give us the welcome mat to be humans. And you help us to sort of realize, like what's happening behind the scenes, you know, there's another emotional equation of anxiety equals uncertainty, times powerlessness. And one of the biggest challenges in an organization sometimes is there's a lot of uncertainty. But no one is talking about what's happening behind the scenes. And so therefore, people get anxious because they don't really know what's going on. So vulnerability is a form of transparency often, and that's a good thing.

Now, the other piece of what they said is that you're a visionary too, so you're not just a vulnerable, because if you're actually just being vulnerable, and you're wallowing in your pity, or you're just that, that definitely doesn't work. But the visionary piece helps us to see we're vulnerable. We're worried we got some stuff we're gonna have to figure out. But the visionary said, pieces, like the confidence, so another way to put it the vulnerability and confidence. And I think that that, you know, it comes back to what Jim Jim Collins wrote about in I think it was good to great. And he talked about leaders who have ambition, hum, mission, humility, or humbleness, with ambition.

And I think that combination of polarities, is valuable. And so yeah, being vulnerable and being confident, are two things. It's hard to imagine someone who has both of those qualities. But if you have both of those qualities, and you can actually really develop with those qualities. And you can understand as we teach an MBA, we if we teach alchemy, like in life, you're going to be an introvert and an extrovert, you're gonna have gravitas, you have levity.

One of the things that you get better at as you age is understanding the alchemy of what's needed right now. And so there's times in organization, what's needed is vulnerability. And whereas other times what's needed is the visionary, confident person. And, you know, when I was on stage, that time I was the vulnerable person, but people also know me as the confident one as well.

Nik Tarascio

So when you talk about alchemy, can you can you go deeper into that? Because I think that's a it's an interesting term, and it's probably something that people wonder a little bit more about.

Chip Conley

So alchemy, you know, in the history of humankind was about turning things into gold and, and there's, there's an element of you get these raw materials that you bring them together and it gets better as a result of the fusion. In the context of what I'm talking about. It is learning how to take two things that are opposites and to be able to be wise enough to understand when are you curious and when are you wise, you know, when I was at Airbnb, you know as as well In the modern elder there, they the three founders said should be our modern elder because you're as curious as you are wise. And that's a form of alchemy.

You know, curiosity and wisdom seemingly are opposites, but they're really not. They they are different qualities, but you can embody them in one person. And so alchemy speaks to the idea of being savvy enough to understand what does this situation need right now? In the polarities of these two things? And do I have have a built the skills in both of those areas, so that I can offer both? So yeah, that's what you know, I think, and I've been called a social Alchemist, which really just means I'm a mixologist, people. That's a different firm walk in here.

But I do love the idea of being a mixologist, the people, and I do that pretty well. And that's the extraversion side of me. But as I've gotten older, I've gone back to something I was like when I was young, which is to be a little bit of an introvert. And it's part of the reason I like write writing books is a very solitary task. And I appreciate solitude.

Nik Tarascio

So for a guy who appreciates solitude, it sounds like you are bringing together tons of people throughout the year with the modern elder Academy. Which I find again, it seems like it's a little bit of both sides at the same time. And I'm really curious again, what was that moment for you and you had the clear vision of this is what I need to build?

Chip Conley

So when I was at Airbnb, what I learned what two things number one is, when I was going to age 45 to 49, I had just the lowest time of my life, and all these things that went wrong during that time woke me up to Okay, I need to sell this company at some, you know, a couple years, which I did at the bottom of the great recession. And then I went into my 50s and I had the best decade of my wife, not just because of my Airbnb experience, but a lot of other things too. So the tale of two midwives.

When I was in the my full time role at Airbnb and moving into a strategic advisor role, I decided to move down to Baja, we're at a home on the beach and write a book was didn't work the making of a modern elder. While I was here, I had this aha, aha, this epiphany, which was why don't we have midlife wisdom schools? Why don't we have a place where people can go to reimagine and repurpose themselves in the middle of their adult lives? And so that idea really sprouted also, because I lost five male friends to suicide, all in midlife during the great recession. And so there was a part of me that felt like, you know, what, if a place like mea has existed, for some of my friends who really felt like they're getting the Game of Life wrong, they felt like they didn't have a lot of options, they lost confidence in themselves. And, you know, so I just, you know, we the midlife suicide rate in the United States is 60%, higher today than it was in the year 2000. So there's something going on here. And there. We have all kinds of programs for adolescents. But were the programs for middle essence, the people who are in the middle of their life. And they're going through hormonal, emotional, physical and identity transitions, and middle lessons. And yet, we have almost nothing in the way of social programs to support the.

So that's what we do. I mean, a lot of the people who come are very successful, and they're sold their business and they feel lost. Some of them are getting divorced. Some of them are empty nesters, some of them have lost their parents. Some of them totally change their career. But we also have some people who come to the tug of war on scholarship, and they are really in need of some of the tutelage that frankly, some of the more experienced and and successful people in the program can work can help them but I'll never forget this two people, Clint, he was a retired investment banker, and she was a retired social worker. And they both still wanted to work, but they didn't know what to do. He had a lot of money, but very little purpose. shedload purpose and not a lot of money. Man did those two learn from each other. And so what we believe that wisdom is not taught and shared. And that is the beauty of our program as we curate our workshops or cohorts the week on cohorts, and they definitely learn from each other.

Nik Tarascio

That's incredible. I'm curious if were there elders in your life that guided you? Was there kind of a blueprint that you found or you had to build this from scratch?

Chip Conley

You know, it's interesting that my favorite mentor story is a guy that I never met a guy named Herb Kelleher, who was the founding CEO of Southwest Airlines and manly company for 37 years. I tried to call him because I wanted to learn about culture. I admired selfless culture, and I wanted him to be my mentor from afar. When I was in my early 30s, I talked to his assistant and she said, now you know He can't take your call. He's a busy guy, but write him a letter. If you really liked your letter, he'll respond to it. I did. And he responded three weeks later, with a letter back to me in the next 10 years, I have a pen pal relationship once a year sending a letter to her or her getting his advice.

So I would just say that generosity of spirit is a big piece of this, I think, you know, we have to have boundaries of how we spend our time. And Herb and his assistant had boundaries, they were not going to take my call. But having, you know, writing the letter and giving her the time to respond, whenever he had the time was a solution for them. And I've tried to live by that myself by trying to be very generous with my time, with some limitations as well. So and then, you know, my father has been a wonderful mentor in my life as well.

Nik Tarascio

Is there anything that you can share? I mean, again, I'm going to go to the modern elder Academy. I'm so curious about the curriculum as someone who's facing the What now, I mean, I feel relatively successful, career wise, but craving something more and trying to figure out how to do and I'm a little early for it, but still trying to figure out now if I

Chip Conley

Listen to your I mean, you're an older millennial, and if I'm not mistaken, right? 42. Yeah. So you still like on the cusp? A little bit? Yeah, millennial Gen X, you know, about 16% of the people who come are millennials, which is surprising. We had a workshop just last week with Blake McCarthy's started TOMS shoes, and me. And it's called entrepreneurship at any age. And of the 27 people in the workshop. Five of them were between age 2031. So average age is 54. Which makes sense. So we've had people from as young as 28, as old as 88.

But yeah, I think it's really the program is dedicated to people who want to live a life that's as deep and meaningful as and as long and who want to actually cultivate and harvest their wisdom, and maybe even reframe their relationship with aging and not be scared of, you know, midlife and what midlife can offer.

Nik Tarascio

So is there is there some nugget of wisdom or advice you would give to someone who's just coming up on that edge and at any age, whether they're 30 or 50, and just starting to face the what now? What is that nugget?

Chip Conley

You know, the one of the things we do in our program is help people navigate midlife transitions of all kinds. And just know that any transition is really three stages and think of the caterpillar to butterfly journey. There's the ending of something the caterpillar in the process of no longer being Caterpillar, there's the messy middle, the liminal middle period, where in the case of the caterpillar, the spins its chrysalis and goes in there, and it's gooey and dark. But that's where the the the magic and the transformation happens. And then on the other side of that, that's the beginning of something new. And very few of us have ever been taught the anatomy of a transition, like I just mentioned here, nor have we been given this tools to master transitions. I almost like transitional intelligence tq.

So I would just say for anybody who's going through the middle of their life, know that if you can actually understand what transitions you're going through which stage you're in, and then learn some of the things that we teach around, you know, what's the what's the transitional toolbox you have, you'll be well suited, you don't have to come to Baja just to do that either. We also have online programs, including a workshop, an online six week course called navigating life transitions, that goes into this in a lot more depth.

Nik Tarascio

Fantastic. Well, I love to close with the question of what is it that you dream about now?

Chip Conley

What I dream about is I do about I've been a client disrupting but I don't think any entrepreneur purposefully says I want to disrupt. So let's be clear. We're already doing the disruption. People are calling us a disrupter in this. And I just want to say what I'm going to do about is making a difference in this way. Number one is two disruptions. The first disruption is helping to disrupt higher education. Helping higher education realize that not all the people they should have on their campuses are between 18 and 24. And that there's a whole collection of people who probably at age 50 should consider taking a gap year and maybe going back to a gap year Academy on a college campus. And college campuses are now doing that. And we're helping them to set those up.

And I think midlife wisdom schools, like MBA are going to become, you know, replicated out there. And then the second thing that I do out is the idea of what we do with our regenerative communities, our residential communities built around regenerative farms or ranches, that what needs to be disrupted is retirement communities. And not a lot of people my age or your age aspired to live in a retirement community someday. But 60 years ago, that was the thing and So how do you create? How do you instead create a community based upon regeneration as opposed to retirement? And so these are things that dream, because I really think there are two big ideas whose time has come. I'm funding them. I'm going to be looking in 2023 develop as critical industries and all this as well.

But, you know, I've made I made a big commitment, a time and money to show to show this as a very noble and worthy endeavor. Because I really believed that as the you curve of happiness research shows, those do a Google search on that account. You know, after age 50. Generally speaking, people get happier with each passing decade. And a lot of people don't know that. They think like Man, if I can survive a midlife crisis, I get to 50 It's just like disease decrepitude and death. But in fact, actually, people get happier with each with each passing decade after 50.

Nik Tarascio

Well, I want to thank you in advance for paving the way for my retirement years to be more about regeneration. That sounds really fantastic. And I'm really interested in longevity and, you know, really changing health span right feeling like it's not just how long I live anymore. It's how I feel. So really excited to see what you pull off and given your track record, I've, I'm sure we're gonna be seeing some really cool stuff. One of the recap again, I'm going by I'm coming, I'm coming. I really love the idea of alchemy. Just wanted to say that I've been after you said that my head was spinning of like, how much in my life am I thinking I'm either A or B and it really is a little bit of the two polarities at the same time. So I think that's a really cool concept to reflect on.

And ultimately just wanted to invite everyone if you're resonating with chips message, check out the modernelderacademy.com And check out his books peak emotional intelligence, sorry, emotional equations and wisdom at work. And last but not least, check out his daily blog wisdom.

Well, and Chip just thank you so much for the time and again really, for me, I had no idea where to look and having stumbled upon you. It's just been such a great gift and I'm really excited to be intentional in this transition instead of just be a little bit aimless and lost in the process. So we're grateful to connect with you so much.

Thank you for listening to the dream beyond. I hope that you received whatever message or inspiration you were meant to get from today's episode. Had a great time recording it for you. If you love the show, please take 30 seconds to subscribe rate and review it. That really helps get the word out. And if you want to connect with me, you can find me at:

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