The Modern Elder

Nov 28, 2018

By 2020, a quarter of all working people in the US will be 55 or older, but our youth-oriented culture leaves many of them feeling invisible, undervalued, and threatened by younger folks in the workplace.

Chip Conley is an American hospitality entrepreneur, author, and speaker out to change all that. He’s ushering in a new way of thinking—embracing the value age brings to one’s life, career, and the workplace.


Chip: I have spent my life being predominantly a social alchemist in the form of hospitality, whether it was a boutique hotelier or for almost six years now as a senior person at Airbnb mentoring the founders and leading part of the company.

Now I am the founder of something called the Modern Elder Academy down here in Baja, which helps people in midlife navigate through transitions. But I think in terms of who I am, like underneath all of that I called my first company Joie De Vivre, which means joy of life.

Jeff: For someone that's done as many things as you have, you've got to find this common thread that weaves through all of those different things.

Chip: I really appreciate the idea of helping people find joy in their life.

Jeff: This is what you bring to the world. You provide people with joy.

Chip: Yeah. Well, there's a great old, I think it's a Mark Twain quote. There's the two most important days of your life, the day you knew when you were born and the day when you figured out why you were born or something along those lines. That why question, that question of like, what is it that you're on the Earth to do and what could you become world class at, is a really fundamental question. I wish we did a better job in people's younger years helping them imagine that.

Jeff: Yeah, and now that notion of bringing joy to people in midlife and beyond is a passion for you. It's a tricky phase of life, getting to that place myself.

Chip: I was lucky enough in my 20s to figure out that being in the business of making people feel joy or helping them feel joy felt like the right path for me.

Jeff: I want to unpack that a little bit, this notion of the modern elder. Can you describe what that term means to you?

Chip: Yeah. Well, the origin is that six years ago, the founders of Airbnb had this little tech startup and they wanted to become a hospitality brand globally. And they brought me in to help mentor Brian, the CEO, one of the founders. And I joined the company and immediately realized, oh my God, I'm twice the age of the average person here. I was 52 and the average age of the person there was 26. And I was reporting to Brian, who's 21 years younger than me, while also mentoring him. So it was an interesting situation.

What I realized pretty quickly in a tech company, having never been in a tech company, I could pretend to know what they were talking about. I had to be as much of an intern as I was a mentor. So what did that mean? It just meant that I had to be curious and wise at the same time. So I believe a modern elder is different than the traditional elder. The traditional elder of the past was held in reverence and the modern elder is appreciated for their relevance. And that relevance in the form of having some timeless wisdom but applying it to modern day problems. So it does require a certain amount of learning and curiosity about the way the world works.

So they started calling me the modern elder at Airbnb and ultimately, I ended up starting to write a book called Wisdom At Work To Make You A Modern Elder. And while I was writing that book, I started imagining the fact that we don't really have much of a safe social crucible for people in midlife going through transitions to come together and try to figure out how to repurpose their life if they're in the midst of a transition, whether it's a divorce, an illness, a career, empty nest syndrome, menopause, whatever it is. There's a lot of transitions in midlife and yet, unlike most other periods of peoples' lives, we haven't really created some kind of celebration or ritual during this time.

Jeff: It's funny because you mention the word "elder" and t has two very different connotations for me. this notion of the elder as someone with knowledge and held in high esteem. But then on the other side, we have this word like the elderly. And at least like in the modern context, the elderly feels to me is like, oh, well that's someone in an assisted living home that's not really contributing society anymore or they don't maybe have the same value to society as maybe they once did. And it's sort of like your reclaiming the word in a whole different way.

Chip: Yes. First of all, I don't think elder without the modern piece is a great word because it almost speaks to patriarchy in the past. And so I think modern elder is that nice oxymoron of current day and ancient or current day and timeless. But the reason I think it's relevant is we have five generations in the workplace for the first time and power is cascading to the young like never before because of our increasing reliance on DQ or digital intelligence.

And yet, we somehow expect these young digital leaders who are founding companies and growing them globally overnight and becoming billionaires, we expect them to somehow miraculously embody the relationship wisdoms and leadership skills that we older workers have had decades to learn. So I think the idea of pairing a brilliant young technologist, potentially, with someone with two or three extra decades of experience is not a bad idea, not because the young person is not an adult but because the young person has great potential and this is just to help support their potential.

And I think elder as a word is a relative word and it's relative to who you're surrounded by. You can be an elder at age 40 if you surrounded by 20 year olds.  If power is moving 10 or 15 years younger and we're all going to live 10 or 15 years older, we've created this irrelevancy gap that's like 20 to 30 years long. And so there are a lot of people who are really, let's say 45 to 65 is what used to be middle age or midlife. Today, midlife is almost 35 to 75 because some people start feeling irrelevant earlier and a lot of people are going to work longer.

So there's a lot of people that I've met who are, let's say, 45 and older who are feeling a bit anxious and bewildered by an era in which power is moving younger and they know they're going to live longer. So the idea of, how do you reinvent yourself in midlife is not new. People have talked about it for a long time and in fact, I think reinvents a little too strong of a word. It's really just repurpose yourself, actually figure out what you've gotten good at and then figure out how you repurpose it out there in the world where people could use it.

So for the time being, I'm using the term modern elder, but if someone comes up with a better term, I'm open to it.

Jeff: With Airbnb. From the outside, that company looks sort of like this hospitality company, but my sense is it's really like kind of a tech company. What did you bring into that company that perhaps they lacked? To no fault of their own, I mean really, just because they didn't have the experience.

Chip: Well I was brought in to help it become a hospitality company, but I learned pretty quickly that a lot of my hospitality knowledge was old school boutique hotel knowledge, like how many rooms does a maid clean in an eight hour shift? It didn't matter a lot in the home sharing world. So, my fact knowledge didn't matter a lot, but my process knowledge mattered a lot, and process knowledge means how do you get things done around here? And because I'd worked in an organizational context, I understood what do you do to make sure you're doing things in a process where people are actually brought along. But also being able to sit in a room with a collection of people and read people and their underlying motivations well enough to understand what it is that's important to them. And so that was important.

Another thing that was important is I think the first half of your life is about accumulating and the second half of your life is about editing. And so, Airbnb needed a really serious editing job on our strategy and I wasn't hired for strategy.

Ultimately, about a month into it, Brian said, you know what? You're the head of the global hospitality, but now you're the head of global hospitality and strategy because I like the way you think.

The idea of listening, there's a great old phrase which is knowledge speaks and wisdom listens. And so, in many ways I think I was appreciated because I was really good at listening to people about what they want to do with their career or what they want to do with their team, etc. So I, over the course of my own six years there, I've mentored over a hundred people at Airbnb and often it's been a mutual mentorship. I'm learning as much from them as they are from me, but I think the part that they appreciate from me is a lack of judgment.

Jeff: And in some ways I mean, wisdom in that sense is not sort of just the accumulation of facts, it's almost like more of a moral character, right? It's almost being able to have the presence to know what your deficiencies are as much as where you're strong.

Chip: Hm. Interesting. I like that. Yeah.

Jeff: Hm. Yeah. Hm.

Chip: Yeah. I think that's true and I think it's knowledge and wisdom are two different things. Knowledge is almost like an addition equation, it's plus, plus, plus, plus.

Wisdom is the opposite. Wisdom is actually a division equation. So it's taking all of that knowledge and then distilling down what's important and what's the essence of something. And I think you can do that when you've been around longer.

Jeff: But things kind of started and stopped with you. Was that a difficult transition now, to be more focused on the growth of other people around you versus yourself?

Chip: Yeah. Well there's two parts to that question. One part of it was not difficult and that is that in my early years running my own company, I was mentoring a lot of people. And I really did my best to create an incubator for entrepreneurs where people really got smarter based upon just mentorship.

The second part is absolutely true though. It was really difficult moving out of the role of being the face of the company. And having my identity attached to sort of being the person who got all of the attention to moving from the sage on the stage to the guide on the side. And basically being the person sort of on the sidelines helping to support these three young founders to become as effective and successful as they could be. It did require some right-sizing of my ego. It meant having a different sense of what made me feel proud. I mean sort of like having kids. When you have kids, you start feeling a sense of pride in your kids.

And so there was an element for me of being open to the fact that I was no longer trying to be the more interesting person in the room. But I was more the most interested person in the room. So I was the person who really wanted and supported you to be successful. And that part, the mentorship piece of that wasn't too difficult. The ego and public side of the acclaim took me a little while. And it also took me a little while to sit in meetings where Brian was running the meeting 21 years younger than me.

Jeff: That's interesting. You're sitting there and your biting your tongue in a way.

Chip: So, I really learned to intern publicly and to mentor privately. And that meant that when I was giving feedback to someone who was a couple decades younger than me, they didn't feel like their father was embarrassing them in front of their friends.

Jeff: The process probably created a tremendous amount of trust between the two of you.

Chip: Mm-hmm. Yeah, it was really interesting.

There was a beautiful interview that we did on my book tour at the Commonwell's Club in San Francisco. It was me and Brian on stage with a woman and Julie Hannah technologist interviewing us. And it really gave us the opportunity for the first time in the almost six years we worked together to show what we did in private, in public. Because Brian would come over to my house all the time and I have a backyard cottage. And we'd go there and sometimes for hours at a time, three or four hours we would meet and talk about things. And all the sudden we took what we did in private and we took it in public on stage. And it was a beautiful experience to sort of show the mutual mentorship because it was really both ways. I think that there were so many things I learned from him as well. And I think that's really to me that's the future.

Jeff: Right. Well, let me ask you about that because typically as one gets older it's not just that one's bones ossify. How one's brain and one's soul to some degree can ossify too.And you can essentially lose the curiosity to grow, to learn. How do you stay open? How do you stay curious?

What are those techniques that you're using at Modern Elder Academy that break people open and allow them to continue to grow even in mid and late life?

Chip: Well there's a kind of asking questions, a method called appreciate inquiry. And appreciate inquiry is... a way for people to use their questions so that they can be catalatic. And so that they are actually having the means of helping people imagine possibilities.

A question to be an illumination or it can shut someone down depending upon how a question is asked. I think that the key is just understanding how do you tap into your underlying curiosity? What is it in your life that you're curious about? And then how do you use that curiosity and passionate engagement to show up with your energy.

One of things that's been really interesting is I've had a lot of people in mid-life ask me, how do you interview for a job and try to pretend that you're younger than you are? And whether it's Botox in the face. Or whether it's the wardrobe you wear or the language you use.

And what I believe is the following... Is when you show up with curiosity and passionate engagement, your wrinkles disappear. Because what shows up in their place is your energy. And when I say energy, I don't just mean the [woo] side of energy, although that's part of it. But the energy is literally this person is on it, this person's engaged. This person is not slowing down.

And that sense of energy is what people are often looking for.

I mean, as a number of people have said, some publicly in the media, if Travis at Uber had had a modern elder next to him like Brian did at Airbnb, he might still have his job as CEO of that company. So, I think that more and more venture capitalists and private equity firms who are investing in these young, brilliant geniuses with their business ideas are imagining not just having sort of people on their board that will help give some influence, but they'll actually literally embed a senior leader or two or three or four, a modern elder, in the organization.

Hire a CFO who's in his 50s or her 50s. Hire a CMO who's got 20 years of experience. But don't hire them just because they're old. Hire them because they are wise and curious at the same time. So, those two qualities, curiosity opens up the door, and it opens up possibility. Wisdom distills it down to what's important. So, one is opening up. The other is distilling down, and that combination of curiosity and wisdom properly matched with young people with big ideas and a lot of ideas can be really helpful.

As one person said to me the other day said, "You're creating a new verb. humaning. You're someone who just helps to human people," which means that in essence our peak as a human physically is in our 20s. Our financial peak, in terms of salary, tends to be about age 50. Although in the Silicon Valley, it's 45. But our peak as a human, in terms of understanding ourselves and having the pattern recognition of ourselves and others and our emotions, is later in life. It's probably our 60s and 70s or maybe 80s.

Jeff: Yeah. So, tell me a little bit-specifically about the Academies. There's one in Baja. What are the events? How do you go, and what's the experience like?

Chip: Well, first of all, it's a social enterprise. So, half the people, more than half the people are on some form of scholarship.

But the idea is that people arrive on a Sunday, and they leave on a Sunday, and in-between, they learn a lot of the things from my book. But we've taken what's in a book and turned it into an experiential workshop format. people learn how to shift their mindset, but at the end of the week,They learn about what does it mean to shift your mindset, and what value comes from that.

Because people come into the workshop with a set of certain mindsets and during the course of the week, we help people to shift out of that mindset, partly by really helping them re-establish and clarify what their mastery is. Let me use an example. One of my friends, Mike Reilly, I went to college with him, and he's a fraternity brother of mine. Mike, for 20 years, was in the golfing industry. He was a sports agent for some of the best golfers in the world. 20 years into it, he lost his job because the company got sold. A private equity firm bought it, and they got rid of everybody who was senior and had big salaries.

So, all of a sudden, Mike was trying to figure out at age 43 what to do next, and he felt like the only thing he'd ever done was golf. His father had been President of Professional Golfers' Association, so this is a hard thing for him to figure out, and then he realized, "Okay. Maybe I'll go into sports management." He got a Master's in Sports Management, but he didn't totally love that. And then, finally, years later, it took a long time. He finally realized that the number one thing he was doing while being a sports agent to these famous golfers, who in their 40s were no longer going to actually be on the Tour but would instead design golf courses, license their name for products, go out and give speeches or write books, he realized that the main thing he was doing is that he was a professional career coach for people in mid-life.

And so, that ultimately led him to becoming the CEO of UC Berkeley's Executive Education Program, which is predominantly people in mid-life trying to figure out they're going to do next.

Jeff: Isn't that funny? I mean, in some ways, we're so busy doing that-it's not always clear-what our-personal mastery is. I mean, if I even just kind of look back at my own career-...I was promoting music shows and putting bands on tour in front of big audiences and at festivals, and then that inspired me to start Wanderlust where we were then really promoting and producing these festivals all over the world. Now, I'm kind of into commune, and when I think as I've had a little bit more time to self-reflect, it wasn't ever really about the music business or the wellness business or a digital online platform. For me, it was about convening people, creating community. That's just what I am instinctively drawn to, but it took me a long time to actually put my finger on what my real calling was.

I don't want to use the word mastery because I think I'm still working on it, but I think it is funny that we don't always know. We're instinctively drawn to the things that we're best at, but we don't always really know what they are.

Chip: Yeah my piece of advice for you if you want it is, "Don't think that mastery is a place you get to. It's a process." Absent the fact that you're not there yet, doesn't mean that you're not in the process of becoming a master. Yeah. So, I mean, I think more than anything being willing. The thing that we talk a lot about in the Academy is being willing to be liminal. To be liminal is to be in-between two things. It's in transition state. It's like the caterpillar to the butterfly. In-between, it's a gooey mess in a cocoon or a chrysalis, but life is full of transitions.

It's just that frankly, when we get to mid-life, we somehow think that we're supposed to have mastered the ability to go through a transition when, in fact, a lot of people shut down because they realize they don't know. It's okay not to know.

And it's okay to actually look like a fool. When you were going through your foolish puberty period, everybody laughed at you, and we're all doing it together. Well, why couldn't we do the same in mid-life? And the stakes may be greater because you've got kids, and you've got a reputation to uphold, et cetera, et cetera but honestly, that process is almost stunting people's growth in mid-life.

Jeff: It's sort of maybe we lose the willingness to be vulnerable. We have this wonderful  phrase that because people need to grow whole instead of grow old. Right? Instantly, to me that means- having a full kind of serene confidence about kind of who you are in your path in the world and being open to being vulnerable even when you're 55 years old, and you're supposed to know everything, and you ... I mean, I've started using vulnerability kind of as a synonym for courage. It's almost the same thing, I mean from a whether you're a soldier walking into battle, or you're walking into a situation where someone might have more power than you. It's almost always the same thing, and it's hard to do that, you know?

Chip: Mm-hmm. Mm-hmm. I love that.

Jeff: Yeah. We could go probably for many different episodes, but I really appreciate you for so many different reasons.

Chip: It's hard, but it's doable. I can vouch for that.

Jeff: Even though we're of a similar generation.

Chip: Oh, well, this has been fun.

Jeff: I do look to you and your career, and how you've been able to navigate a lot as a role model and as a mentor.

Chip: Thank you.

Jeff: Could it be that the secret to thriving in our mid-life is, as Chip said: "learning to marry wisdom and experience with curiosity, a beginner's mind, and a willingness to evolve?"

More and more global companies helmed by young people are starting to truly value the knowledge that comes with age and experience.

Lest we forget: while technology will continue advancing, the human-centric skills that mid-career workers possess--like good judgment, specialized knowledge, and the ability to collaborate and coach - never expire.

So perhaps it's time to retire that old fearful mentality of feeling threatened by the "digital natives" nipping at our heels, and instead, opt for a shift in perspective.

Thanks for listening to the commune podcast. I'm Jeff Krasno. Until next time.

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