How to Navigate Mid-life Transitions as a Modern Elder – Chip Conley, MBA – #1045

You're listening to the Human Upgrade with Dave Asprey. I've got a well known guy here in the studio in Austin with me. His name is Chip Conley. Chip runs something called Modern Elder Academy, and he's helping people cultivate wisdom and he's working on understanding different generations, especially in the workplace. Now, if you're young, this episode is for you. You're in your early 20s, maybe you're 30. And you're saying, I'm not that young. Well, you're kind of in the middle there, but you're certainly not 90. Right. And Chip's working on how do we get three generations together to share knowledge. And it's really impactful and profound when you do that. I even put my Burning man camps together that way. I want a couple elders, I want a couple of young people to pick up heavy things and run around and get us all excited. And then a mix of people in the middle because that's actually how societies work. Chip learned all this stuff because he started working at this tiny, tiny tech startup you might have heard of called Airbnb, as head of global hospitality and strategy years ago. And he was twice the age of the average employee of the company when he came in and. And he got the title Airbnb's Modern Elder, which led to where he is today. Chip, welcome.

Well, I'm glad you. Thank you, Dave. And as a founding board member of Burning Man, I appreciate the call out because Burning man is the kind of place that is incredibly intergenerational for those who've never been there. They're surprised by that, frankly. The founders of Burning man were. They're boomers. So it's a really great mix of people, and I would love to see that utopian world mirrored throughout the world.

And you're also a New York Times bestselling author. These are mostly business things. I'm talking about business and marketing and some emotional equations around happiness. And you kind of shifted from one to the other. I'm just looking at questions I could ask you that maybe no one's asked you before.

So.

When did you first become aware of your elders having something of value to you? How old were you?

I was, you know, I was probably a kid. I was a kid and it was my grandmother Nani, my dad's mom. The other three grandparents I had. I can't say that I learned a lot from them. They were fine people, but they were drinking by 4 in the afternoon. Long story short is my grandmother Nani, she just had a sparkle in her Eyes. She had a. She had a joie de vivre. I started a boutique hotel company in my early 20s or my mid-20s called Joie de Vivre, partly because of my grandma Nani, because I used to say to her, you've got a joie de vivre, you've got a joy of life about you. So I learned a lot about happiness from her, about it's not something you pursue and instead of pursuing happiness, you should practice joy. That's something I learned from her. And yeah, so she was special. She was the one who lasted the longest. She was the last of the four grandparents to pass away.

What do 20 year olds not know about, say, 60 year olds that they should know?

Well, here's the number one thing. I would just say about 20 year olds because I started doing this when I was 28. You can become wise at any age.

Yes.

So Modern Elder Academy MEA is the world's first midlife wisdom school. But I've met lots of people who are wise at 25 and not wise at 75. So my definition of wisdom is metabolized experience that leads to distilled compassion. And the reason, the second part of that is because wisdom is a social good. If you're savvy or shrewd, you might metabolize your wisdom for your own sake. But if you're actually doing it for the benefit of somebody beyond yourself, then there's a distilled compassion piece. But the key thing to know in your 20s is the thing. What I learned at 28 was I was an idiot CEO of a boutique hotel company. I had one hotel. Did you ever go to the Phoenix Hotel in the Tenderloin? Sort of a rock and roll hotel? No, no, it's just like this funky rock and roll hotel in the Tenderloin. I bought it when I was 26, didn't have a lot of family money.

How did you buy a hotel when you were 26?

I bought it for $800,000. Can you imagine buying a 44 room hotel in San Francisco?

That's a good deal.

Well, we didn't own the land. 40 year land lease.

Okay.

But yeah, I bought it and then I spent $200,000 renovating. I mean, like, so I had a million one that I had to raise to do it. And so, yeah, a million one won't go very far in San Francisco today. You might get a studio condo.

Yeah. And a bag of needles.

Yeah, that too. So I still own that place 35, 36 years later. But long story short is when I was 28, two years into owning that hotel, we had the Loma Prieta earthquake.

Oh, yeah, I remember that.

And I was up shit creek. I mean, I just didn't know what to do. We lost all of our business. I had no cash. And so one weekend I went home and a friend of mine said, you need to start writing in a diary. I think he was just tired of hearing from me kvetching. And so I pulled a diary off the wall and I wrote on the front of it my wisdom book. And from that point forward, I, every weekend would sit down. And now, 34 years later, I still do this. And I sit down and I write four to six or eight bullet points of what I'd learned that week. And by doing that, I was actually metabolizing my experience. I was taking my life lessons and making them tangible. So you could do that at any age. And I think that the thing I'd say to someone in their 20s is learning lessons is part of what life's all about. But then actually using those lessons for your good and for the value of others is the opportunity of wisdom.

There's a little piece of advice in there that maybe listeners didn't get is that you wrote it down because every day you have wisdom points that come up. But we are programmed in our meat operating system to forget. To forget the good stuff, to forget the wisdom, and to just stay worried about, you know, not. Not running out of food and being safe and all that. And if I look at any of the work I've done around integration, whether it's psychedelic or from the neurofeedback school that I run, if you write it down, it takes it out of the mucky ego, subconscious, unconscious thing, and it crystallizes it, even if you never read it again. And if you read it again, you get your wisdom. So you've been doing that for 34 years?

I've been doing that for 34 years. And let me take it even one step further, Dave. You can do this with a team. What you can do is to say once a quarter as a team, you come together and you say, the 10 of you, the 12 of you, what was your biggest lesson of the last quarter? And each person talks about it. And then as a group, you say, what was our biggest team lesson? And that's a great way to not just sort of get clear on what it was, but to actually socialize it. Because actually that's the next step is if you actually talk about your lessons, not only are you recognizing them yourself, but you're actually acknowledging them to other people and you learn it faster that way. And as a team, you share the wisdom. And so at mea, we talk about wisdom is not taught, it's shared. So how do you create the crucible for wisdom to be shared in a way that is serving everybody?

That is a really cool idea. I'm going to start doing that with my group of companies.

Yeah, it's easy.

It is easy. And then you have the organizational learning. The more I've run multiple companies, the more I see each company almost as a person. It's an information field, and individuals come in and they leave over time. And at what point, if everyone in the company's been replaced three times, is it the same company? Well, it is. And all the cells in your body get replaced about every seven years or something, but you're the same person. So it turns out both companies and humans are ephemeral. We actually don't exist except as fields of information. And what that means is that if you can take the lessons learned and you can write them down, that they strengthen the information field that holds things together.

It's the information field and it's the cultural field, too.

Oh, smart. What's the difference?

Information field would be data and knowledge and how we do things. And the culture field would be how do we behave? You know, what are the behavioral norms that you know when you come into this company? Ah, you'll learn them quickly. In fact, they're never written on the wall. There's just. There's the values on the wall. And they say, oh, here's our values. But very few companies say, here's the unwritten rules of how we do culture here. And I like to say that culture is what happens around here when the boss isn't around. That's my definition of culture, and I think so. I think culture is, yes, as you can churn through a bunch of people, but often it's the culture that's still there.

What do you do when you're running a company and say someone's not a cultural fit? They might have skills, but they come in and they do not behave the way they need to behave to be successful in an environment?

Well, I think the first question is. So first of all, I don't know. I don't love cultural fit. I love cultural ad. And the reason I say that is because if it's a cultural fit, it means that somebody has to fit in. And a cultural ad is giving the indication that we're open to exploring having people who don't fit the dominant culture.

So culture evolves for sure. I mean, I'm certainly not a normal person at any organization.

I think we could all agree with that.

I wouldn't have hired me. That's why I'm an entrepreneur. So I'm with you there. I want you to criticize my definition of culture, so I'm gonna share it, and then I want you to contrast it with yours.

Yes.

So I look at culture as like, a school of fish, Right. And they're all swimming in a direction. And if one of the fish just starts going sideways and it's the wrong direction, the other fish automatically kind of get it to go in the right way, so we're all moving in the same direction. And when a culture's not working, that means when a fish goes sideways, everyone follows one fish. Right. Instead of all of the fish moving in unison like a flock of birds.

Well, I think what you've just described is the US Military. But, no, it's not.

They're marching one direction because it's a joint decision where they all go. Sure. It's not like there's one intelligence that tells a school of fish when to turn or a flock of birds when to go. They're all doing it together. But if one of them is completely, like, going sideways, the whole flock doesn't lose its cohesion.

Correct. But I think it. So I think we'd start by saying in terms of the definition of culture, there's no right or wrong culture. So there's.

Okay, a culture of narcissism, sociopathy, and slavery. That seems wrong.

That would be wrong. Totally agree. Totally agree. But in terms of a successful culture, let's say a success. And maybe there's a, you know, a successful narcissistic culture, but I don't think it's. I don't think it's sustainable. Yeah, but there's successful cultures that are very different. Oracle is very different than Apple, which is very different than Facebook.

Very true.

And so I think the question of culture is. I would look at it this way. Culture is what serves the business interests and the people within the business and makes them the most effective as possible.

And maybe happy as well.

Yeah, for sure. Happiness is a big piece of it. So, you know, I'm. I. I've written books on culture, so, you know, my book peak, How Great Companies Get Their Mojo from Maslow, is based upon applying Maslow's hierarchy needs to companies and to cultures. And so I do believe that you have to get conscious about what kind of culture you Want. And this is where most companies get it wrong. They actually don't get clear on, like, what is the culture here? What kind of culture do we want? And. And they aren't. They're not. Nor they're not conscious about it, nor are they explicit about it. And so the hiring process, frankly, is when you determine this. And, you know, when we were at Airbnb or when I was at Airbnb, we had a process where anybody who's getting hired in the company had to go through a cultural values interview of two people in departments that had nothing to do with the group that you were going to be working with. So it could be an engineer who's coming along, and everybody on the engineering team wants to hire them. But if the values interview interviewers didn't like them, then a conversation needs to happen. So there was an element. And so that was weird. I mean, it was a little bit weird. It was unusual, for sure. But I think it had a profound impact on making sure that there weren't these little fiefdoms and these silos of like, oh, the engineering culture is that, and the marketing culture is this, and the policy and legal culture as that. So there was something that actually held it all together.

That's cool. Now's my chance. I got to ask Eric Schmidt a question that I want to ask you as well.

Yes, please. I'm honored.

And for listeners, guys, Eric Schmidt was the. The CEO and chairman of. Of Google. So here's what I asked Eric. I said, okay, scaling the tech isn't that hard. It's an engineering problem, and we know how to solve those. But how in the heck did you scale the. The people organization that big without the narcissists destroying it?

Yeah.

So how did you do that at Airbnb?

Yeah, so Airbnb. So I had to do it at Joie de vivre. But when I. When we grew to 3,500 employees. But when I went to Airbnb, it was a tech company, and tech companies grow a lot faster than, you know, bricks and mortar companies. So I want to give, you know, hats off to the three founders. They believe deeply in culture, and so I. They liked my book Peak, and so they were fascinated by the idea of the peak culture. But what they were really most interested in is creating a culture that actually was going to be around 100 years from now. And Brian, who I acted as the mentor to, but I learned as much from Brian as he learned for me. I called myself a mentor. A mentor and an intern at the same Time. And so they've invested in culture. We did something called one Airbnb. This is a great story. So when we had only about 500 to 1,000 employees, we started it and we kept doing it until we had 3,000 employees. And then it became too expensive. But we had to look for other approaches. So we brought every single employee from 22 countries around the world to San Francisco for like a four day love fest. And it was a way for us to once a year and then ultimately every other year, bring everybody together, help people to be on the same page in terms of where we're going, mission wise, business strategy wise, but most importantly, help people to feel the culture. You know, because pre. Pre Covid. Pre. Pandemic. Yeah, the idea of something palpable that you could touch was exceptionally important. You know, we're learning in this era that, you know, how do you do that in an era of zoom? But back then we made the investment to say, let's bring everybody together. And I think what it did was it meant that we had fewer of. I mean, we didn't have that many coaches in the company because we didn't need coaches so much because there was a sense that often the coaches were someone helping someone deal with a problem that in. On a team or in terms of their own purpose. But we had, you know, we had mentors. We had like a mentorship program that helped people to feel like, I don't need an outside coach coming in and telling me this. I need an internal culture minded mentor who could do that. And I had over 100 mentees over the course of my seven and a half years at Airbnb, which was a lot.

What a cultural difference. Do you want to know what Eric said?

What did he say?

He said, well, we identified that we had. They had knaves and some other word whose name I'm forgetting right now. So basically, people were bad actors building empires. Those were the knaves. And then they had these other people who were basically weird. Maybe not a cultural fit, but high producers who HR didn't like, maybe, but who were not doing anything harmful. They were just odd. And I think it was like knights and knaves or something like that. He had a great thing for it. And he said the knaves were the problem. Those were the narcissists building their own little fiefdoms. And he just said, public and traumatic firings. He said, we only needed a few of those. And then the rest of them left the company. And I was like, wow, like, talk about a difference of culture. Right. Like we will hunt you down, we will find you, you'll exit the company, you know, the walk of shame with the box kind of thing. And that way everyone else who's playing tricks knows. And here you are with like mentors and mentees. But you had to make a bad hire. What happened when you were, oh, you.

Made lots of bad hires and there were people. I mean, the hiring process is essential, but someone will make it through and then show up with their true self. And how do you deal with that? So one of my favorite tricks with someone who's not showing up the way that we want them to is to ask them, what are the five adjectives you want people to use to describe you? And so I get the five adjectives and then I say I'm going to go out to the dozen people who you work with the most and I'm going to ask them a few questions, like a 360, all anonymous. And one of the questions I'm going to ask them is, what are the five adjectives that best describe you? And then we're going to see. And so get those five adjectives from the people who work with them, look at them and compare them with that person's five adjectives. And you do the comparison and say, okay, none of your five adjectives are showing up here. So let's go back to your five adjectives and let's say, what are the habits or the behaviors or the hacks that we can actually put in place? If you want to feel like you're an empowering leader, what do we have to do to help you to be empowering to the people you work with? And that worked. That worked. And sometimes it didn't, sometimes it didn't work at all. And when it didn't, that's when it was clearly time to say, no more, this isn't working. And then you move on. Yeah. And quite frankly, when someone's habitual in some of their personality flaws, my favorite question to ask in an interview is, what's the number one way you're misperceived in the workplace? I love this question because what it forces someone to do is to go off script. Because a normal job interview can be just so rote and it forces them to go off script and say, wow, okay, am I self aware enough to know how I am misperceived? And if I say that, how's it going to come across? And so people sometimes get really flustered with that question. But that question was the number one question that Worked for me because it allowed me to go down the rabbit hole with them based upon their answer. And so they say people think I'm an asshole, but really I'm a nice guy. I was like, okay, let's talk about that. How are you? Why is there that misperception? And so it ends up almost being like a therapy session.

Sounds like it.

But quite frankly, that's what you got to do. And so that kind of question helps to weed out the bad apples.

One of the things that you're working on with the modern elder academy is this kind of midlife coaching. I don't know, midlife. What do you call it?

Wisdom school.

Wisdom school. I like that. I'm thinking back to a time where I was having a really serious problem when I was running bulletproof with an employee, and it just didn't make sense. And I was dealing with a narcissist. And narcissists will make you think you're crazy. That's their operating system. I've studied it. I'm probably gonna write a book about it, because not about that one experience, but just about the pattern recognition to be able to find them. It's a society, society wide problem that's getting worse right now. But I sat down with my friend Ken. I'm not gonna say his last name. I don't know if he wants that kind of publicity, but he runs a $500 million real estate company. And I mentioned the problem, and he looked at me, and he picked up his phone. He said, oh, you need to fire her. Are we going to use my phone or yours?

No.

This is a guy who's probably 10, 15 years older than me and had seen the same pattern. And since then, I've talked to so many entrepreneurs, people with 10 plus years as CEOs, and we all have had this experience, but no one really talks about it because it's actually kind of shameful. And I actually waited another six months that were incredibly traumatic and probably cost me $100 million to make the decision.

Oh, wow.

But, hey, you live and you learn, right? And I asked him, how did you know this? Like, how did you know to do that? And he said, oh. I said, mentors. And said, really? Well, who mentored you? He said, jack Welch.

Ooh, I don't know if I want Jack Welch as my mentor. Jack had some positives, and he also had some negatives.

He did, right?

Yes.

But, you know, a vaunted business leader, like, how do you do this? And he said, oh, I got to know him 20 years ago, and I just formed a relationship, and I could call him, and he would just give me advice. And that's where I want to ask you this question. So wherever someone is in their career, if you want a senior executive in your back pocket who can mentor you, how do you ask for that? What does mentorship look like?

Couple thoughts on this. So I'm going to tell you a quick story.

Sure.

So when I was in my early 30s and my company, joie de vivre, was growing quickly, we ultimately grew to 52 boutique hotels around California. I knew that culture was important, and I knew that I wanted to learn from the best. So I called up Dallas, Texas, and I said to the operator at Southwest Airlines headquarters, I want to talk to Herb Kelleher, the founding CEO of Southwest Airlines. And she put me through. And I got Colleen Barrett, who was his assistant, his executive assistant, one of.

The most powerful people in the company.

That she was very much then, and she ultimately become president of the company. How does that. And EA becomes a president. I love that. And I said to her, I said, my story is I'm a young CEO, and I want to learn culture from the best, and I would love to learn from Herb. And she said, well, he's really busy, but if you write him a letter, he might respond. And so, basically, long story short is I wrote him a letter. Three weeks later, I got a letter back with answers to all three of my questions. He said, you asked me two of those three questions no one's ever asked me before. You're welcome to write me once a year. And so for the next 10 years, I wrote Herb Kelleher a letter.

Wow.

This is pre Internet. So these were all written letters, and he would answer them. And ultimately, I think Colleen was answering some of them in the later years. But long story short is your mentor doesn't necessarily have to be someone you've ever met. Now, you may have to have the chutzpah to say, I'm going to reach out to whomever and see if they respond to me. And most of the time, they won't. But wisdom is not wisdom. Doesn't have to be local, doesn't have to be the person who's down the hall from you. Doesn't have to be someone who lives in the same place as you. Doesn't even have to be someone you know. But back to your question. How do you ask the question? Well, first of all, you don't pop the M word too quickly. Marriage is not popped on the first date. So go out and get to know the person. And the number one piece of advice I have is to say, ask the question of, like, I want to learn about how to run a great meeting from you. I want to tap into your wisdom. Say that at the end. I want to tap into your wisdom. Tap into your wisdom is something that's hard to turn down. And wisdom is something everybody appreciates when it's applied to them. And the more specific you are about what you're looking for, the easier it is for them to say yes. Where a potential mentor is worried is that you want a long term marriage relationship. And there are really two kinds of mentorship, and we teach this at MEA at the Modern Eldritch Academy. The first kind is the librarian. When you're the librarian as a mentor, your role is to share your know how and know who. And the mentee's role is to ask you great questions. And that's what I did with Herb Kelleher. Asked him the questions, he answered them. I learned something that's a finite role. And so if you want that kind of mentor, then you might be specific after the second or third conversation to say, I'd like to have you be my mentor, just to ask you questions occasionally. Perfect. The other kind of mentor is a much more comprehensive relationship. It's what I call the confidant and the confidant. I came up with that word. It's not a, you know, not an unknown word. But I came up because there's a woman at Airbnb who was from France and I was. She was directly reporting to me. And two months into me working with her, she said, chip, you're my confidante. And I said, lisa, you haven't given me any juicy details yet. And she said, oh, no, in my part au France, a confidant is the one who gives you confidence.

Oh, that's a different definition.

Exactly. And she said, you're my permissionary. You're the one who gives me permission, but you're also the one who helps me understand how to be successful. So that's a different kind of relationship. In that kind of relationship, I was the one asking the questions. She wasn't asking the questions. I was asking the questions. And the questions really were almost like being a coach, almost like being Bill Campbell being the person who just said, hey, here's a few questions like, you know, what did you learn in the last week? Or, you know, how'd that meeting go? You know, what do you think you could have done better or, you know, more? I Use appreciative inquiry a lot, which is a form of asking questions that helps show possibilities and opportunities. And like, what do you want your role to look like a year from now? And what are the key things skills you want to have learned by then? And so a confidant relationship is much more comprehensive. You can't have that many confidant relationships. You can have a lot of librarian relationships. So distinguishing between the two is helpful for you to determine whether you can say yes or not.

As a mentor, it feels like a lot of people in their early to mid career need confidence and permission as you described. And maybe as you become more of an elder, you don't need confidence and you don't need permission because you're just going to do it and you either going to fail or not. And once you realize that, you don't really even need confidence because you're not.

Afraid of failing, you have some pattern recognition. Let's start by saying if you have metabolized your experience, you've created some wisdom. Women actually, in particular, as they get older in the workplace, get more confident. Men's confidence actually starts to plateau a little bit in their 50s, whereas women's continues to escalate. And there's a lot of reasons for that. But long story short is, yeah, I think as we get older, but you can have a mentor at any age. And let me also, let me talk about my mentor relationship with Brian Chesky. He asked me to come in and help democratize hospitality. That's what he said. That was his opening line. Chip, I want you to be my in house mentor to help democratize hospitality globally because we want to be a big player someday. And this is when nobody had ever heard of Airbnb. And so I said, okay, let's talk. And what I learned over time was that he was my mentor as well. So we mentored each other. I mentored him around emotional intelligence and leadership and strategy and frankly, the hospitality and travel business, the business, the industry he was disrupting. He taught me so much about venture capitals capital. I never had a venture capital in my own company investing in me. And so I learned about that. I learned about basically product, I learned about technology, I learned about cultural changes that are happening due to millennials. And so the best kind of relationship, in my opinion, is a mutual mentorship because it means that you're gonna learn from each other. It's full of reciprocity.

I really like that perspective on it.

And wait, one other thought on that. We live in an era by the year 2025. Two years from now, the majority of Americans are gonna have a younger boss. We've never seen this before.

Interesting.

As a.