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Entrepreneur, author and speaker Chip Conley joins the program to discuss the importance of treating age as we would other types of diversity in the workplace. He shares his own experience of joining the disruptive startup Airbnb when he was in midlife, and the lessons he learned along the way. He also reveals his perspective on generations in the workplace, and how a sense of shared meaning and purpose can unite workers from all age groups.

In this episode you’ll discover:

  • Chip’s diversity story (4:30)
  • How Chip created a diverse workforce in his role as CEO (12:30)
  • The importance of “mutual mentorship” and what that entails (16:00)
  • The industries that tend to focus on older workers as part of their diversity efforts (23:30)
  • Chip’s perspective on generations in the workplace (29:30)
  • How purpose can unite generations in the workforce (32:30)
  • The advantage that Millennials have experienced (36:30)
  • How we can measure and evaluate belonging in the workplace (40:30)
  • The benefits of ERG’s for employees and companies as a whole (43:00)
  • Chip’s “Modern Elder Academy” and how to attend (46:00)

Listen in now, or read on for the transcript of our conversation:

JENNIFER BROWN: Chip, welcome to The Will to Change.

CHIP CONLEY: Jennifer, it is a pleasure to be with you.

JENNIFER BROWN:  Thank you. I am thrilled to be meeting you through the opportunity to have this interview. I picked up your book Wisdom at Work: The Making of a Modern Elder. I actually personally have been attending a fair number of conversations and conferences lately about life after 50 in the professional and personal sense and as an organizational development person asking the question particularly what is life at work and bringing your full self to work look like after 50? And how are employers and companies embracing the potential, and the performance, and the knowledge and capability and wisdom of our quote/unquote elders?

We’ll talk about that word in a moment. I know you have a lot of thoughts about it. But I just wanted to thank you for writing this book. This is something that I think is not talked about often enough. You’re really an opening shot across the bow and a challenge, I think, to all of us to bring our full selves to work at whatever age we are. But also, a challenge for organizations to think more carefully about this, be more proactive and really embrace all that their workforce has to offer. I really thank you for your work.

CHIP CONLEY: Thank you. I am honored.

JENNIFER BROWN:  I know, right? It’s a privilege to study these things and to represent voices that aren’t represented and heard and that’s exactly what you’re doing. I know that this is personal for you as well and you just fill the book full of anecdotes about how you arrived here at this message and feeling the importance of writing a book like this. We always start The Will to Change with our diversity stories. I would like to invite you to share what your diversity story is?

CHIP CONLEY: Well, it’s interesting I’ve got to components to it. I grew up in a predominately white neighborhood in southern California in Long Beach. Although Long Beach has the most diversity in the United States, so it’s a very diverse city but as is true in many cities the little white enclave was there. The beautiful thing is the public high school district was such that my predominately white neighborhood was part of a very multicultural school district. The place that I would go to high school was in downtown Long Beach, a place called Long Beach Poly High School. Quite famous because it’s where Snoop Dog went to high school and there was a very strong hip hop movement and the band War from long ago, Why Can’t we be Friends went to school there.

So, here I am this sort of curious white boy, as I was called back then, in this school that was predominately non-white. I just thrived. I thrived partly because it made me culturally curious. It helped me to see that the dominate narrative that I had seen both in the US culture but also in my neighborhood and in my family wasn’t necessarily the same for an immigrant family from Vietnam. This was back during the date of the boat people so to speak in the mid-1970s. Or, an African American family that had four years of lineage, four generations, all living in the same household as was true of one of my friends. There was just really a great opportunity at a relatively young age to understand diversity day-to-day not just as an interesting culture anthropology exercise, but literally it was my life for all those years of high school.

The other diversity story for me was I think that level of diversity woven into me helped me when I was 22 years old and living in New York at that time, come out as a gay man which was really quite hard. I was an All-American athlete. I share a name with my father, I’m a chip off the old block Stephen Townsend Conley, Jr. My father was a captain in the Marine Reserves. I’m pretty much of a hardcore hard ass kind of guy. I was the only son and the oldest of the three kids and so the idea that his oldest son of the Marine Captain was going to be a gay man was not easy for him to digest and not easy for me to tell him. But I think the fact that I grew up in a very diverse high school helped me to realize there was not only a singular path in life which was the path that my father would have had for me.

Fortunately, it took a couple of years of difficult times with him, but he got to a place where he embraced me and ultimately my youngest sister also turned out to be a lesbian and so two of his three kids of a very traditional quite conservative parents ended up being gay.

JENNIFER BROWN:  What a story. I can only imagine what that was like. I came out when I was 22 as well, oldest child. Very difficult and yet you probably look at all of it as a gift. I’m curious, I always think the struggle of coming out and articulating what is important to me, who I am, learning to stand up for myself, learning to value that and actually really prize it now in terms of my resilience, my courage and commitment to my own authenticity is so powerful. I never would have had that if I hadn’t had to kind of define myself separately from the script that I had been given and really make my own way in the world. I don’t even think I would do what I do now if I hadn’t gone through that. Is that what it felt like for you in hindsight when you look back at it, as a gift?

CHIP CONLEY: I think when you’re going through something that is awkward, difficult and is new to you, you don’t realize what level of emotional and maybe even spiritual growth you’re going through. It serves you later. There’s a boo by Viktor Frankl Man’s Search for Meaning about this experience of being a psychologist in a concentration camp as a Jewish psychologist who lost his family and to distill that beautiful book on meaning down to an equation, it would be despair equals suffering minus meaning. Suffering is always going to be out there in life, there’s no doubt about that so it’s almost like the constant and so the two variables here are despair and meaning. The more you can find meaning, especially in a difficult time, the less despair you have.

While I don’t think I was despairing in high school in a diverse environment, it was a struggle at times. That level of finding meaning in it and for me to find meaning was really feeling like I was a more empathetic human being and somebody who understood cultures different than mine, that was a beautiful learning that I think has influenced me as a leader, especially leading diverse groups of people, the rest of my life.

JENNIFER BROWN:  The empathy it generates. The ability when you experience the outside or being an outsider, the empathy you have for other outsiders and the ability to perceive that and kind of be a voice for that is transformational. I think that’s very true. You spent many years after having found Joie de Vivre Hospitality Group at age 26, the ripe old age. It was the second largest boutique hotel brand in the world which you sold in 2010 and joined Airbnb. Is there anything about that period in your life that you want to share with this audience in terms of maybe what we’re talking about? Did you feel you could bring all of who you were to that role? What did it teach you that you’re taking into this next stage?

CHIP CONLEY: Yes. I went to Stanford undergrad after my high school years. I went to Stanford Business School directly from undergrad which was sort of unusual and I graduated at age 23 from Stanford Business School. I then went to work for a real estate developer. I almost like went to work for my dad.


CHIP CONLEY: He was a macho southern dude who is somewhat homophobic, etc., etc. It was like, “Okay, well let me test this out.”  I did well with him and we’re actually good friends now and he’s mellowed a lot just like my dad has as well. But the bottom line, in that process I realized I wanted to be my own entrepreneur in the commercial real estate development area. I decided to create Joie de Vivre, which means joy of life in French. Our mission statement was also the name of the company. That gave me the ability to really put my talents directly into the workplace.

The thing that is interesting about being gay and a CEO, and this is 32 years ago. Being Tim Cook as the CEO of Apple as a gay man is hard, I’m sure, very hard. But being a gay CEO 32 years ago was a lot harder.

JENNIFER BROWN:  Yeah. Hats off to you, seriously.

CHIP CONLEY: What was beautiful about it is that plus my diverse background in terms of my high school gave me the ability to sort of understand everybody and to ask people to bring their best self to work. I’m not asking you to bring the self that you think – you don’t have to mirror me, I want you to bring your best self to work. The process for me of being able to express myself and not feel embarrassed about saying, “I’m sort of good at design.”  When I was a high schooler the fact that I was good at art and design, I was also sort of a macho athlete, but I was good at art and design and it was something I was embarrassed by. I was also embarrassed by the fact that I liked writing. I sort of felt like these were feminine qualities and therefore I didn’t get a chance to really exhibit them.

Then my first boutique hotel I got to use those. I got to use my empathy. Again, empathy as a testosterone while male in America doesn’t necessarily mean that you show vulnerability or empathy and yet I was able to do that as well. One of our leaders in the company at one point in the company called me a vulnerable visionary. A vulnerable visionary and I liked that.

JENNIFER BROWN:  I love that.

CHIP CONLEY: It was really those are two different energies. The visionary piece can be quite bold and maybe full of confidence and something that sort of speaks to thinking big. The vulnerability piece though is what allowed me to create a workplace where people could authentically show up for who they were. At the end of the day, when I grew the company to be a large company with 3,500 employees, the leadership team was more woman than men, about one-third to 40% LGBTQ, very racially diverse and that kind of workplace where people knew Joie de Vivre was a company you could go to no matter who you were and it was a meritocracy and you could grow. You didn’t feel like you had to fit into a certain kind of demographic to be successful in the company.

JENNIFER BROWN:  Then you somehow find yourself crashing into the world of tech and I’m curious what was that like? What was the contrast like between the hospitality world and the tech world when you began to do your work in 2010 with Airbnb? Take us back to that moment.

CHIP CONLEY: It was actually a couple of years later after I sold the company that I started spending time with Airbnb. But there’s a great quote from Robert De Niro in the movie The Intern.

JENNIFER BROWN:  I love that movie.

CHIP CONLEY: He says, “Musicians don’t retire, they quite when there’s no more music left inside of them.”  I was 52 years old when Brian Chesky reached out to me. Brian was the cofounder and CEO of Airbnb. To be honest with you, six years ago Airbnb was not well known, and I barely knew anything about it and I’m a hotelier in San Francisco where they were headquartered. It was not something I knew. The sharing economy was a new phrase that I never heard of. I did not have an Uber or Lyft app on my phone six years ago and so it was a different era.

What was so different again, about me now joining this company Airbnb, was I was twice the age of the average employee. Now there’s a diversity question again. This is a company that was full of people in their 20s. Fully maybe 90% of the employees were Millennials. Here I was, as the old guy there who had zero tech background but there were a lot of areas where I could bring my cognitive diversity as well as my years of experience in pattern recognition. I think wisdom is really about learning the patterns of your life, especially learning and understanding the patterns of your humanist and your humanity and humanity of those around you.

I was able to bring that, and I had a profound effect on the company. Which in saying, it feels very boastful, but ask Brian Chesky what the company would have been like without me. They would have done pretty well but the thing that I really think helped was we did sort of an EQ for DQ trade agreement. What I brought to the table, which I didn’t expect because I never really thought of it this way was emotional intelligence. That could be embodied in leadership skills, thoughtful strategic thinking that is very long term minded as opposed to short term. It meant that I was good at collaboration which in a young tech company filled with young men can actually sometimes be a challenge, that element of everybody being very competitive can work against creating a great team.

But what I got in return from these young people was the DQ. I gave the EQ, the emotional intelligence and the DQ was the digital intelligence. That’s where I learned a whole lot from these folks. Not just about how to use my iPhone better but just to understand how to create – I didn’t even know what the word product meant. I thought product was our homes and our apartments at Airbnb. No, product was the software application of our website. I ended up learning a whole lot. What we were doing often was what I called mutual mentorship where often I was mentoring people younger than me, but they were mentoring me as well.

JENNIFER BROWN:  Hence the “mentern,” right.

CHIP CONLEY: That’s correct. Mentor and an intern combined.

JENNIFER BROWN:  Right. I want to talk about that in a little bit, what you mean by that and how you view the sharing of knowledge across generations in the workplace and how that should look. But I want to ask you about you find yourself at Airbnb and you shared covering your age. We talk a lot about covering in my work for diversity when we talk about bringing our full selves to work. There are many of us that don’t feel that bringing our full selves to work is going to be accepted. We typically think of that in terms of race and ethnicity, or sexual orientation, or gender identity, or certainly gender.

Some of who we are is very visible like our age like our gender. Then other things we can hide. People like you and I can choose when we come out in a business setting. We have that, but some people in the gay community don’t have that choice. I wonder, were you bringing your full self to that new opportunity and what was that evolution like where you’re at this point now years later writing a book on the modern elder? I’m curious.

CHIP CONLEY: I think the thing that has been true for me for my whole life is there’s a famous Oscar Wilde quote which is, “Be yourself everyone else is taken.”  It’s a beautiful quote. It’s is a cliché in terms of just be yourself. People say it all the time. The number one piece of wisdom people give each other. It’s sort of obvious, but I think it’s a good reminder especially in environments where we feel like we’re supposed to fit into someone else’s standard. I think with Airbnb what was beautiful was I was open to being curious.

I think one of the challenges for people in midlife is you’re supposed to feel like you know it all and especially if you are positioning yourself as a mentor or an elder in some way. What I think the modern elder is as much a curious learner as they are a wise teacher and that liberated me. In terms of it liberated me in all kinds of ways. When you’re the curious dumbest person in the room, it meant that I wasn’t trying to live up to some standard. It also meant frankly, that I wasn’t trying to be perfect and I wasn’t trying to portray a certain image. All of that allowed me to just be who I am and yes, who I am includes things like I am a gay man. But I am also an older guy. I’m a Boomer I’m not a Millennial. I was about to embrace that rather than trying to pretend.

It was interesting, early on in my time there an engineer who I write about in the book, we’ll call him Q because frankly, he didn’t want me to tell anybody that I was having these clandestine meetings with him. He’s a 53-year-old engineer and he was doing everything he could to look and act younger than his age because he was scared if people actually figured out his age, they would figure out a way to get rid of him. After 35 in Silicon Valley an engineer is perceived as it’s time to go out to pasture. Here you have a tech company that’s one of the most prized employment opportunity for any engineer in the world at Airbnb and so it was interesting to have that conversation with him because I felt so badly.

In fact, at one point I said to him, “How do we help you come out?”  He’s a straight man and he’s like, “What do you mean?”  I said, “I don’t mean that you’re going to be gay. What I mean is come out as 53-year-old. Join our wisdom at Airbnb ERG our employee resource group.”  Which is basically an ERG, an alliance of people who were 40 years old and older in the company. Just like you have in many bigger companies you have this for woman, or LGBTQ, or for people of color; we had this for older people. He said, “I could never join that group because I’d be outing myself that I’m older than 40.”  Mind you, this guy is 53 years old.

JENNIFER BROWN:  I think people might know.

CHIP CONLEY: Yeah, exactly. The thing I helped him to see and ultimately what really, I think in chapter six of the book in his story, his name is John Q. Smith but we called him Q as sort of his code name, as I said, “Listen, you have skills as an older engineer around collaboration and being able to help train and teach those young minds that are coming in that are going to be very valuable to the company.”  Once he saw that he could embrace what he does well which may not be the normal thing that an engineer is known for at Airbnb, they’re usually known for the loner late night programming of coming up with amazing code that creates all kinds of new paths for the website. Great, that’s what a young 22 coder who is a genius can do. But as a 53-year-old engineer who leads and manages other engineers you can help them understand how to live up to their potential and how to collaborate well.

Once he realized that’s the evolution he could have in his identity and his skillset he embraced it. Carl Jung, a famous psychologist said, paraphrasing, “You can’t live the afternoon of your life based on the way you lived the morning.”  He was really speaking about what is midlife and midlife is the afternoon of life. The premise here is you’ve built some skills along the way so the way you show up as 53-year-old surrounded by people half your age is going to be different than the way you showed up when you were 23 years old.

JENNIFER BROWN:  That’s right. I mean, you split life into three phases. It’s about physicality, physical strength and then it becomes economic strength in the middle and then the human, the wisdom in our third-third of life. We move from the striving for perfection to the embracing of wholeness. It just felt so – gosh, it was like a bomb for the soul that I didn’t even know I needed as I was reading your book because I’m in my late 40s, but I’ve never been better and different. I do think we as a society don’t celebrate the ways that aging actually makes you smarter, makes you wiser, makes you more value added. Makes you a critical part of teams, as you said earlier, how we are thinking about creating multigenerational teams where everybody compliments each other because there’s so much that each generation brings.

I wonder, are there other employee resources group related to mature workers, however that’s defined? Is that spreading across Silicon Valley or other industries? What do you see?

CHIP CONLEY: In Google they’re called “Grayglers”, the Google “Grayglers” as in gray people who are Googlers. At Uber they’re called Sage, the Uber Sage Group. Frankly, in most traditional companies this kind of older ERG is not that important because ERGs are primarily focused in most companies on whoever is the minority. If you’re in an old school company filled with people generally who are 45 and up, you wouldn’t really need an ERG for this. In Silicon Valley it’s quite the opposite and therefore the idea of a wise/mature employee ERG group is definitely spreading. I think more and more what we’re seeing is tech companies are realizing that diversity of age is maybe as important as diversity of gender, sexual orientation, race, etc.

JENNIFER BROWN:  It’s interesting. Do you also hear stories, I know I do, about younger leaders actually covering their age, doing the opposite in terms of I’ve had Millennial leaders, for example, stand up and say, “I’ll tell you something I don’t talk about at work, I don’t want to celebrate my birthday, for example, at the office because I have big dreams for my career. I have multi-generations on my team, and I have a lot of authority for somebody that’s my age and I don’t want to highlight how young I am to have all that authority.”  Which I always think is really interesting. Everybody on the extreme ends of the scale are navigating different issues but they all are experiencing the stigma and sort of the pressure to downplay who they are. I hope these ERGs help lift some of those behaviors.

What do you think some other ways are of normalizing, to use an overused word, our comfort with who we are at all stages of life besides the creation of an ERG? What are some other companies doing that really honor all ages at work?

CHIP CONLEY: I think that Procter & Gamble is sort of an old school company, been around a long time but that is really an innovative company in a lot of ways. I went to their headquarters in Cincinnati last summer and I came to realize one thing they’ve done, and they have a really long-time long-term employee workforce and they have a mastery program. Once you’ve been in the company for 10 years you can apply to it and become a master. If you’re a master, it means you’re sort of an internal consultant internal coach. You’re somebody that they parachute into teams that are struggling and so you help bring some institutional wisdom and some collaboration skills in there. These folks are the folks who help acculturate new employees in the company. They can become mentors.

It’s sort of like at Google where engineers can apply for 20% time which in theory means that they can work only 80% on their core job and they can focus 20% of their time on new initiatives, entrepreneurial initiatives that they think the company should actually be considering. Why wouldn’t companies do the same for their modern elders, where those folks can actually have their core gig that they do for the company, their scope of work, but they could actually have this other element as well?

I think we’re going to see that start to spread. I think we’re also going to see companies be more thoughtful about the process of tapping into their older employees who are starting to get to a retirement age. I think retirement as a word, we’re going to look back on 20 years from now and say that was absurd. You learn until you’re 20 or 25, you earn until you’re 65 and then you go out to pasture for 30 years. Yes, when you died at age 72 it might make sense, but longevity is growing in the country amongst most groups. Although actually, the last two years I’ve seen some reduction in longevity in some groups as well because of opioids and suicides spiking.

But long story short, I think the idea that people on a Friday are working 100% for a company and a Monday they’re 0% is an absurd idea because it’s sort of like, “Wow, that institutional wisdom walks out the door Friday afternoon and you lose it.”  That doesn’t make any sense to me at all. I think more and more companies, especially with an unemployment rate in the US under 4% is how do they retain those people? Maybe they go from 100% to 60% in the first year and then 40% in the second year and maybe in the third year you’re down to 20% and then they retire after that fine. But it’s a three-year process in which both the employee who is going to be leaving and the company get great benefit out of it.

JENNIFER BROWN:  That’s right. As a Gen Xer, it’s interesting we always feel like the forgotten generation or the ignored generation.

CHIP CONLEY: You are the forgotten generation.

JENNIFER BROWN:  I know, I know. I’m not just being paranoid and cynical which is typical of our generation. Yes, we are the disillusioned.

CHIP CONLEY: The slackers. The slackers of the world.

JENNIFER BROWN:  Exactly. I don’t feel like a slacker I will tell you. But I do think it’s very interesting to see the Baby Boomers staying in the workforce longer perhaps often because of not only greater health and longevity but economic necessity. It’s sort of this cap on the movement within the pipeline and as a Gen Xer, I haven’t been in corporate for years and I think a lot of us solved this problem, by the way, by going outside and becoming entrepreneurs if we could. But those of us who stayed in the organizations, we’re getting sort of blocked on the top end of the funnel and we’re also a tiny generation, we’re half the size of Boomers and Millennials and we certainly didn’t have this kind of passionate voice on our own behalf. I would never characterize our generation as having that or being willing to do that.

Then we have this Millennial generation coming up who has been very encouraged in a completely different way in terms of bringing their full selves to work, demanding a certain contract and values alignment with their employer. It’s very interesting. Each of our generations is sort of fighting for relevance and a place in the pipeline and for the pipeline to leadership, but what are some of those dynamics as you see them occurring? Do you have some advice for the different generations that depends on what is the age of the audience you’re talking to?

CHIP CONLEY: Sure. First of all, I have some blasphemous things to consider here. Number one, I think generations are an arbitrary concept in the sense that who is the wise person that said, “Okay, the Gen X group ends on this year?”


CHIP CONLEY: It’s an arbitrary construct in some ways. In some ways it’s not, “Okay, if you’re a year apart and one of you is a Millennial and one of you is a Gen Xer you have completely different experiences.”  So, let’s start by calling a spade a spade here because that is just how it is. I think that is an important thing to be aware of. Secondly, we don’t fit into the stereotypes necessarily of our generations, so let’s just respect that not everybody fits these. I think thirdly, many of these things are stage of life issues as opposed to generational issues.

The fact that people in their 20s tend to be self-absorbed whether they’re Boomers, Gen Xers, or Millennials is just true. People in their 20s are self-absorbed as an element of it’s your early days of being an adult and an independent spirit in the world and so that just happens. I would just say that’s the first thing, is just know that some of the things that are going on here are more about stage of life than anything. But I actually think some of them are specific to the generation.

The Boomers had radical roots in some ways, or had liberation roots, had the roots to say, “We don’t want to live the life of our parents,” which was sort of this Eisenhower we all live in the suburbs. As adults we didn’t necessarily want to live that straight arrow path. What that means is that the Boomer generation has a certain entrepreneurial flare to it. Underneath sometimes how they operate as an older an adult is some idealism still because there is a lot of idealism that came out of the ’60s and the ’70s, even though it was a very disaffected period in the ’70s.

I would just say Boomers have the ability to tap into – as you get older sometimes the idealism starts to wane on some level but I think what I see is that sometimes a Millennial a Gen Xer and a Boomer can all tap into idealism and if you’ve got an idea that’s got a lot of purpose attached to it purpose can be a really beautiful collaborative tool for bringing people together. As for Gen Xers, yeah, I think there’s an element, it’s weird it’s a generation that by nature the way we sort of see the generation seems a little disaffected, seems a little bit disillusioned and then yes, we made them the smallest generation as well. It’s like, okay they feel victimized.

But I think the thing about what Gen Xers had going for them is they are a very independent spirited group. I think there’s underneath the cynicism of all the Boomers that got all the attention – I think of Gen Xers as the middle child or the younger child. They’re not the oldest child in the family that got all of the initial attention and was preened and properly groomed into being a leader. No, I think a lot of the talents that the Gen X generation speak to being an independent spirit and really tapping into that.

I think the thing that’s interesting from a stage of life perspective for people who are Gen Xers, and just let’s be clear Gen X would be about approximately age 38 to about age 55 or so right now. I would say that’s about the right range. That’s a really difficult time of life. The U curve of happiness which has been shown across all cultures shows that generally speaking people go into a downward decline in their level of happiness starting in their mid to later 20s that actually bottoms out around age 45 and starts to show some improvement in the late 40s around 50.

Just know that there is history that shows that this is a period of life that can be quite difficult. We randomly come face-to-face with our disappointments. It’s when we come face-to-face with the consequences of decisions we’ve made along the way. It’s when we actually feel the accumulated debt of all the things, we have added to our lives whether it’s having kids, or a mortgage, or being a volunteer for a bunch of things, or having many roles in a company, or all of the stuff you’ve acquired over your life. That accumulation gets you to a place where you say, “What’s important here? Who am I?”

Those two questions of what’s important here and who am I allows for a potential radical realignment of who you are in your late 40s early 50s to align yourself with who you want to be moving forward. I say in the book the first half of your life is about accumulating, the second half of your life is about editing. That editing function is what starts to kick in the later part of this era, maybe the early 50s late 40s.  Let’s just be respectful of Gen Xers, they’re going through a difficult period.

The finally the Millennials, there’s all the promise of being youthful with Gen Z being right behind them. I think one of the things that is different about Millennials as a generation is the dominate technology of their era gave them huge career growth. The dominate technology of my era was a television and unless I became a TV producer and advertising executive, it had zero effect on my career path. Yet for these young people today, Millennials, their dominate technology that they grew up with is something that absolutely propels their career forward which is why there’s a little bit of resentment amongst the Gen Xers and the Boomers towards Millennials because in fact, they got a real advantage as a generation.

I think what we have to teach people who are younger is the face of their iPhone is not the same as the face of the person sitting next to them. That’s why I think the emotional intelligence EQ, is particularly important in terms of how we curate great leaders and managers. That was long. I’m talking too long.

JENNIFER BROWN: No, I loved that. It was so good. It reminded me of a lot of things and taught me a few things as well. I just can’t leave this topic without asking you about Generation Z, folks that are what 18, 19, 20 and younger? Do we know about them yet?

CHIP CONLEY:  I think there’s a lot of studying being done on them. I don’t think necessarily there’s a dominate stereotype yet of what Generation Z is other than the fact that they’re the ultimate digital natives, even more than Millennials today. I think there’s a sense where the Millennials are very fluid in technology, the difference between them and Gen Z is Gen Z is fluid in mobile technology. Not all Millennials are fluent in mobile technology. The iPhone is only 12 years old so if you’re a 38-year-old and the iPhone came out when you were 26, that doesn’t necessarily mean it was integrated in your life completely.

On the other hand, if you’re a 20-year-old and the iPhone came out when you were eight, it was a formative part of your upbringing. Anything that is mobile, whether it’s Snapchat or Uber, both of those are things that you don’t do necessarily, or Instagram, you don’t necessarily do those on a laptop or a desktop and so you’ll just find that mobile is sort of central to their life. The risk there is the mobile is like a mirror. It’s like a mirror to your face and you’re starting at yourself and there’s the potential even more so than for the Millennials that there’s a narcissism built into this because it’s all about how you package yourself in the world. I think that’s true of people in their 20s to start with. Millennials even more so because of social media. But take that three steps further with Gen Z.

JENNIFER BROWN: That’s right. You spent so much time at Airbnb and were there for the birth of their whole commitment to belonging at work. It’s interesting, we refer to diversity and inclusion in my world over the years the semantics have morphed, belonging is one of the newest concepts that I think some companies, I wouldn’t say the majority, but everybody is kind of wrestling with what does this mean? I’m so mindful of generations and how they define belonging so I wondered how would you define it today? Perhaps you had front row seat at a company like Airbnb which is so forward and so in the world and so trying to create belonging not just for its guests and hosts but within its workforce, how did you see that manifest? How was it defined there? How does it make you feel? Do you feel like it’s a great inflection point and a prudent direction to go?

CHIP CONLEY:  I think we call it DIB now, diversity, inclusion and belonging. I’ve heard that and a month ago I didn’t know that. Yes, it was fascinating. I joined in April of 2013 and a month later we had an offsite retreat of our senior leaders, a dozen of us, and I helped to lead an exercise in trying to understand what business we are in? What’s the core differentiator and that’s when we really came upon this idea that we’re in the business of helping people belong anywhere. To belong anywhere is a really profound statement. It certainly is a differentiator versus Marriott.

Marriott, another accommodations company is not necessarily in the business of helping people belong anywhere. Once we realized belonging was sort of core and I’m a huge Maslow nut — Abraham Maslow’s Hierarchy of Needs belongs to a piece of that.


CHIP CONLEY:  I wrote a book called PEAK: How Great Companies Get Their Mojo from Maslow. I was like, “Okay, I’m in the right habitat here. Let’s talk about how we even measure belonging.”  What’s really hard is the most valuable things in life tend to be up higher in Maslow’s pyramid like self-actualization, or happiness. But a few years ago, I went to Bhutan to study the Gross National Happiness Index there because they’re the first country actually in the world to actually stat measuring happiness of their citizens and see how they create policies that help support that.

We did the same at Airbnb in terms of saying, “How do we measure belonging? What are the ways we can evaluate whether someone feels belonging, including in the workplace?”  A lot of it had to do with how do we ask our employees questions that denote whether they really are feeling like they belong at Airbnb? Then we started measuring that. It’s a tool that we’ve used and a metric that we’ve used to really understand what’s the correlation between when someone feels like they belong and two things: one is, are they effective in their work; and number two is, do they intend to stay here? There’s enormous correlation between when someone feels like they belong and the quality and effectiveness of their work as well as whether they want to stay in the company and continue to be engaged.

That’s a really important thing to know, wow belonging is in some ways an ingredient for effective loyal employees. That means we needed to drill down further on how do we create belonging. What we talked about earlier is having ERGs and employee ERGs, that’s the kind of thing that actually can help create belonging.

JENNIFER BROWN: That’s right. I know, I have been such a proponent of ERGs for over a decade now because I have always though they helped to offset the isolation of some communities in the workplace who were underrepresented and truly in the minority and also had the stigma of conscious and unconscious bias hidden in every day when you’re different. ERGs are this incredible safe space community. It galvanizes a voice, a collective voice. It helps people find literally friends, colleagues, networking opportunities. It’s a cross functional group of people and employees who are passionate not only about their own identity but also about driving the business forward.

A lot of our consulting work has focused on helping people within a community articulate their value proposition as a business driver. That’s been the evolution from social clubs, or perhaps networking events, or cocktail parties, or whatever particularly the LGBTQ community we’re great at parties.

CHIP CONLEY:  We do like our parties, yes.

JENNIFER BROWN: We like our parties and they’re very fun and they’re colorful or whatever. But we laugh, at my company we say we need to move beyond food, fun and famous people in terms of the programming and the value that we bring to our employer. I think that is changing and I think these groups are almost like little focus groups. They are knowledge bases for companies, should they choose to dive into it and be curious and actually commission these groups to do something valuable like solve a valuable problem and a persistent problem in the company.

For example, it’s not a problem it’s an opportunity of what to do with workers like you said, you just don’t leave work on a Friday and don’t come back on a Monday and poof you’ve retired. You walk out the door with so much wisdom, and knowledge, and opportunity and so much energy and so much health and vitality still to give. Yet, companies are letting people walk out the door and it feels very much like the focus is on younger talent except for the companies like P&G and others who are really asking some powerful questions about this.

I want to give you an opportunity to talk about your Modern Elder Academy. You’re actually going after this. You’re creating an ERG in a way, because you’re creating an intentional offsite to explore what this stage of life means and you’re empowering professionals, whether that’s personal empowerment or professional empowerment to go back to their companies and sort of push and challenge the way that we’ve been looking at different stages of life. Tell us about the Modern Elder Academy. Where does it happen? What’s the curriculum? Who comes? What is your vision for what you want to accomplish with it?

CHIP CONLEY:  A couple of years ago when I moved from a full-time leader role at Airbnb to just a consultant, like a strategic advisory to the founders which I have been doing for a couple of years it gave me the space to write a book Wisdom at Work: The Making of a Modern Elder. I started writing that in the spring of 2017 down in Mexico where I have a home on the beach. As I was writing the book and interviewing 150 people in midlife, what I heard over and over again was the anxiety and bewilderment people felt.

The anxiety of how am I going to afford my retirement years which a lot of people felt like, “I don’t even know. I have barely anything saved and I’m 52 years old.”  The bewilderment of the world that we live in, in terms of today’s workplace where people feel irrelevant at a younger age. That made me start thinking, I’m living in this rural part of Baja California, southern Baja California and now I’m north of Cabo San Lucas on a beach where I’m surrounded by land, beautiful ocean and farm land and tropical beaches and desert. Why don’t I take some of the land around me and maybe buy a few homes around me and put together a campus where people can come and spend a week, arrive on a Sunday and then depart on a Sunday. Where 18 people with an average age of 52 but the range has been from age 30 up to age 74 in terms of who has come through the program, they come and they navigate midlife transitions and look at how to reframe their mindset about aging such that they can repurpose themselves and tap into their mastery often in wholly new ways in the workplace and in life.

We started a year ago on a beta test basis for the first six months and then we opened this recent November. We’ve had 225 people go through the program. Some of the programs are two weeks long, most of them are one week. It’s a social enterprise which means that over half of the people that come are on scholarship because to me what was really interesting was not just seeing a bunch of wealthy people talk about what they’re going to do with their later years without any fear about finances, what was interesting was seeing an investment banker at age 48 who is retired walk down the beach with a 62 year old social worker and she’s figuring out how to have the income in order for her to retire in the future. But he is feeling purposeless.

There’s an element of we all have something to teach each other. It’s the first midlife wisdom school in the world. There’s lots of personal growth retreat centers all over the world but there’s not one that actually has a curriculum, 150-page curriculum plus my book which is a supplement to this that goes in deep learning around a stage of life, which is midlife, and does it in a place that is as in depth as this is. It’s been great. The reaction has been spectacular. It’s sort of the thing I’m going to do next.

JENNIFER BROWN: I can’t wait. I can’t wait for those people to feel refocused, infused with new purpose perhaps, inspired to continue to contribute. My personal agenda with companies, which is where I focus so much, is bringing that wisdom and I guess the language and the value proposition back to companies to say, “We need to do this better.”  The shiny object of younger talent I suppose and all the focus that generation gets from our organizational architects I think is hurtful to diversity. You said earlier, we are really redefining diversity and all the things that we mean by that. I think it’s important to know we’ve come from a place in talking about diversity about identity, race, ethnicity, gender, sexual orientation and I predict, and I think this is happening and you’re seeing it too, every time I ask people to share about their diversity, I get the most unexpected things back from people.

More and more they are about life stage, they are about balancing caregiving and that tricky Gen X role that you were talking about where we’re sort of the sandwich generation. We don’t feel we can talk about the flexible work arrangements that we need in order to accommodate our life so we can perform at work. There are so many further stigmas I think to challenge when we talk about bringing our full selves to work.

I think that’s what is particularly powerful about your focus on age, but really there’s so many diversities within this group that you’re focusing on too. It’s so intersectional. I love it because it contains all of the differences that I think many of us unfortunately got really good at hiding, or downplaying, or not standing up for over the course of our professional lives. Our organizations we worked for I think suffered for that because we weren’t our own best advocates, right? We didn’t know how to advocate I think and what our value proposition really was. I am so inspired by seeing younger people in their commitment to bringing their full selves to work and all that comes with that.

Often when we have these conversations and people roll their eyes about different generations, I challenge people to say, “We all wanted this kind of workplace. We all wanted a place where we could belong and thrive and not spend our valuable energy downplaying or minimizing what we anticipate might be negatively stereotyped.”  We all wanted this. Here is this generation coming in really committed to this in a very unapologetic way. I love that and while we can take a page from that I do think we need to be discovering our own story at this stage in life too. I know that you’re opening up this aperture for us Chip. I want to thank you and I want to close by having you share where people can find out more about you, follow your work, read what you’re writing, maybe even go to the Modern Elder Academy and spend some time in Baja. I’m sitting here thinking, “Hmm, maybe I need to put that on the calendar.”

CHIP CONLEY:  Come on down. People can learn more about what I’m doing at ChipConley.com. If you go to that site you also see a mini site on the book Wisdom at Work: Making of a Modern Elder as well as a more substantial site on the Modern Elder Academy which is also can be accessed at ModernElderAcademy.org. I’m on all social media. I do write articles for LinkedIn. If you go to my LinkedIn profile you will see about 20 articles there that speak very much to the subject of what does it mean to be a modern elder and how do, we create an age diverse age neutral workplace.

JENNIFER BROWN: Chip, thank you for joining me on The Will to Change today.

CHIP CONLEY:  Yes. What a joy and I love your voice.

JENNIFER BROWN: Thank you. I was a singer and I had to learn how to talk and relearn how to talk but thank you, I really appreciate that coming from you.

CHIP CONLEY:  Yes. All right.



Chip Conley

Wisdom at Work: The Making of a Modern Elder

Modern Elder Academy