Skip to Content

As we live and work longer, leaders need to redefine how they think about attracting and developing intergenerational talent. Modern Elder Academy’s Chip Conley is at the forefront of this mindset shift, explaining why “wisdom workers” will take the place of “knowledge workers.” A close mentor to Airbnb founder Brian Chesky, Chip stresses that those in mid-career face both more angst and more opportunity than ever. He provides a roadmap for reframing midlife from crisis to calling, and argues that five generations in the workplace requires a new generational compact.

“I think it’s time for us to reimagine education and disrupt it. Research shows that around 45 to 50, we have our lowest point of happiness in life, but it’s not necessarily a crisis as much as it is a midlife calling.”

— Chip Conley
About the guest:

Chip Conley is the founder and CEO of Modern Elder Academy, a “midlife wisdom school” dedicated to long-life learning. Prior to MEA, Chip founded the hospitality chain Joie de Vivre and mentored Airbnb’s leadership team on their path to scale. Chip is also New York Times bestselling author of Wisdom at Work: The Making of a Modern Elder

About the host:

Bob Safian is the host of Masters of Scale: Rapid Response, and the editor-at-large for Masters of Scale. He’s the founder of The Flux Group, a media, insights, and strategic advisory firm. He was previously editor-in-chief of Fast Company, where he won the National Magazine Award for Magazine of the Year in 2014.

We all encounter inflection points in our career, and with life expectancy growing worldwide, midlife now comes with both more angst and more opportunity.

— Bob Safian
Transcript of Masters of Scale: The rise of the wisdom worker

CHIP CONLEY: I think it’s time for us to reimagine education and disrupt it. Research shows that around 45 to 50, we do have our lowest point of happiness in life, but it’s not necessarily a crisis as much as it is a midlife calling.

If you are a professional athlete and you’re 35 years old, you are an elder. If you’re a software engineer in Silicon Valley and you’re 40, you’re over the hill. If you’re an advertising exec on Madison Avenue.

We have over 3,000 alums now from 42 countries around the world and the big surprise is they are as young as 28 and as old as 88. At any age we can reframe our relationship with aging.

Older people are starting 25% of the businesses in the U.S. today, and they have twice as high of a success ratio as compared to someone in their twenties.

With five generations in the workplace for the first time, it’s time for us to create a new generational compact.

BOB SAFIAN: That’s Chip Conley, founder and CEO of Modern Elder Academy, MEA has built a global community of leaders dedicated to unlocking generational talent.

I’m Bob Safian, former editor of Fast Company, founder of the Flux Group, and host of Masters of Scale: Rapid Response.

I wanted to talk to Chip because he’s redefining how we think about careers and about talent. We all encounter inflection points in our career, and with life expectancy growing worldwide, midlife now comes with both more angst and more opportunity. 

Chip was head of global hospitality at Airbnb, where he helped mentor CEO Brian Chesky. But he says he learned as much as he taught. Intergenerational interplay, he says, will define the successful organizations of the future. 

Chip argues that knowledge workers are destined to be displaced by what he calls ”wisdom workers.”

To stay relevant, as a business and as an individual, Chip says, takes both scale and soul.


SAFIAN: I’m Bob Safian. I’m here with Chip Conley, founder of the Modern Elder Academy. Chip, thanks for joining us.

CONLEY: Yeah, great to be with you, Bob.

Chip Conley on where the idea for “modern elder” came from

SAFIAN: You first came up on my radar as the founder of the Joie de Vivre Hotels, one of the largest boutique hotel collections in the U.S. You then became head of hospitality at Airbnb, helping scale that platform. I did want to start with your latest adventure, the Modern Elder Academy. Our culture is so focused on youth and the new. I’ll confess to some challenges personally, defining myself as I’ve aged. I’d still like to think of myself as modern, and so this framing of modern elder is appealing. What is a modern elder, and where did the idea come from for you?

CONLEY: I ran a company Joie de Vivre for 24 years as the founder and CEO, from age 26 to 50. Then a couple years later, I got this call from Brian Chesky, the co-founder and CEO of Airbnb. He wanted me to be his in-house mentor and the head of global hospitality and strategy. Within a few months, people in the company started calling me Airbnb’s modern elder, and I didn’t like it a lot. It sounded like AARP’s magazine. Then the founders said to me, “Chip, the average age here is 26, and you’re 52, so you are the elder, but you’re a modern elder. A modern elder is someone who’s as curious as they are wise.”

I was very complimented by that. Okay, I’ll be that modern elder. For the four years full-time, and then three and a half years as a strategic advisor to the founders, I was a bit of a modern elder. When I was writing my fifth book called Wisdom at Work: The Making of a Modern Elder, I was in Southern Baja, in Mexico. One day, I was going for a run on the beach. I asked myself, “Why is it that we don’t have any midlife wisdom schools or places where people can go and repurpose themselves?” That’s how Modern Elder Academy came about.

Chip Conley on mentoring Airbnb’s Brian Chesky

SAFIAN: In your time at Airbnb, this relationship that you had with Brian Chesky, you were like his mentor.

CONLEY: I came in to be the mentor. I realized pretty quickly, I was also the intern. Because, while I had a lot to offer around hospitality and travel, understanding leadership, building a culture, but being in a tech company for the first time meant that I had to learn a lot. I learned as much from Brian as I think he learned from me. Sometimes we would call it the EQ for DQ trade alliance. I would give him a little emotional intelligence, which is a skill that we actually build as we age, on average.

But I learned DQ from Brian, digital intelligence. I was learning from someone who was 21 years younger than me.

SAFIAN: You’ve used this term intergenerational collaboration, that there are things that we can learn from each other, which sometimes some older people look at as like, “Oh gosh, all the young people are telling me what to do all the time.” You don’t necessarily react to it that way.

CONLEY: I think it goes both ways. Young people are saying, “Oh man, that Boomer just keeps telling me how the world works.” The intergenerational collaboration idea really was wedded to my perspective of: how do I get things done in a company like this? I tried to be an intern publicly and a mentor privately.

I would ask a lot of questions. I think that really meant a lot of the younger people at Airbnb gravitated to me. As I started spending time with them, I got clear that you can teach me something as well. That’s how a mentern is a mentor and an intern at the same time. We’ve created something recently called Generations Over Dinner. We can find it at It’s a way for generations to come to a meal and have a deep, rich, maybe life-changing conversation. We’ve had as many as seven generations at the dinner table together to talk about topics like purpose, love and relationships, and how to solve the world’s problems. Especially in the workplace, with five generations in the workplace for the first time, it’s time for us to create a new generational compact.

SAFIAN: What is the difference between a modern elder and a traditional elder?

CONLEY: The traditional elder was regarded with reverence, and that’s not so true in most of the world today. But I think the modern elder is about relevance. Relevance means that you take the learning you have, the wisdom you’ve built over time, and you apply it in new environments. I define wisdom as metabolized experience that leads to distilled compassion.

If you look at the history of wisdom, going back to Greek times, wisdom has always been seen as a social good. Wisdom you’ve maybe gained along the way is something you can offer to others.

Wisdom workers replacing knowledge workers

SAFIAN: You’ve said that wisdom workers will be replacing knowledge workers. What are wisdom workers?

CONLEY: So knowledge speaks, and wisdom listens — I’m now quoting Jimi Hendrix. I think knowledge is an accumulation game. Wisdom is more of a division equation. It’s distilling all of that knowledge to what’s really essential. A knowledge worker, that term was coined by Peter Drucker in 1959. What he was saying is that people who knew how to use computers to bring information and data to their decision-making were going to be the most powerful people on the planet. Today, seven of the 10 most valuable companies in the world are tech companies, so knowledge workers rule the world.

All of our knowledge is on the little phone in our pocket. We’re awash in knowledge. What we could use more of is a bit of wisdom. A wisdom worker in the workplace would be somebody who isn’t just filled with knowledge. They’re more about: how do you get to what’s essential and important? When I joined Airbnb, there were a lot of different strategic priorities in the company. There were 30. One of my jobs was to take the senior leadership team to an offsite retreat. We spent three days looking at all of those strategic priorities and said, “Okay, how do we distill it down to just four strategic priorities for next year?” And everybody in this company is going to know which of those four they’re primarily focused on.” I think that helped.

Other things that a wisdom worker does is they’re really good with peripheral vision, being able to see around the corner and to see that the decision you make today could have a huge impact on the organization or its reputation two years from now. There’s a lot of organizations that are full of brilliant young people, and yet very few of them have ever scaled a company the size of what they’re scaling.

And having somebody around who has some experience with that and understands how to process things in an organizational context can be very valuable.

SAFIAN: As you were talking initially about wisdom workers, I wondered how much of it was: AI is going to take over doing the knowledge work, and what’s really going to be valuable are the choices we make, which is what you’re describing as the wisdom, right?

CONLEY: Exactly. Yes. AI, at least at this stage, is not going to take over. But, the reality is AI and wisdom have something in common. They’re both about pattern recognition. Wisdom has human qualities built into it.

For AI, a little bit less so. It’s obviously data-driven, it’s less by a hunch and more by what the data shows. So I think that as a result of that, I think knowledge workers are at risk a little bit in the next few decades. And I think wisdom workers are going to become the rage.

But the other thing about wisdom workers is they better keep their humility in check because that’s really what makes them a wisdom worker. The moment you think that you just know it all is the moment you no longer are a wisdom worker because you’re not being curious enough to realize that you are meant to be not just a lifelong learner, but we at MEA call a long-life learner.

SAFIAN: So we have a president in the White House who recently turned 80. We’ve seen Disney bring back Bob Iger as CEO, even though he’s 71. It calls into question the whole notion of 65 as a retirement age. Is there a change underway in how we view experience versus youth?

CONLEY: As Arthur Brooks wrote about in his book From Strength to Strength, he talked about fluid intelligence versus crystallized intelligence. Fluid intelligence is when we’re very focused and fast. But as we get older, what we get better at is crystallized intelligence, holistic and systemic thinking, the ability to connect the dots. So I would love to have someone running Disney who can connect the dots, or a global organization like that needs somebody who can synthesize. Similar to the government.

The problem I would just say is when someone is in the same position for too long, and what that means is their habitual; they may have lost the openness and willingness to try new things.

Maximizing the second half of our lives

SAFIAN: You’ve said that the Modern Elder Academy is about helping people reimagine and repurpose the second half of their adult lives. Should we be thinking about starting over at a certain point in our lives?

CONLEY: The average age of the people who come to MEA, the Modern Elder Academy, is 54, and they, on average, think they’re going to live till 90. Not too many of us think that in our mid-fifties or later fifties, that we are actually halfway through our adult life. How do we help people to start thinking that way for the first time?

Because part of this is about longevity. We added three decades of life in the United States in the 20th century. What I think we need to start recognizing is that the historical benchmark of: you get to age 65, and you retire. Now it’s really escalating higher.

And therefore, yes, starting something new, learning to become a beginner again is one of the most important things we can do as humans.

SAFIAN: As life expectancy has increased, our life stage expectations have in some ways stayed the same. I often think about how universities, you go to college as a teenager for four years. Well, that system was created when life expectancy was, what, 40.

CONLEY: 40 or 50, yeah.

SAFIAN: In four years, you could become an expert in a way that you could stay expert until the end of your days. That’s just not practical in today’s world.

CONLEY: Careers that we tend to have today versus a hundred years ago are changing much more quickly than they used to. In the next five to 10 years, we’re going to see liberal arts colleges with beautiful campuses in Rust Belt places go out of business because there’s not enough young people, and young people are not valuing the cost of what it takes to get a college education. So I think it’s time for us to reimagine education and disrupt it. Maybe it’s time for higher education to look at creating a gap year academy at age 50. So, you hit 50, you save some money through your 529 education programs, which people think it’s just for their kids but actually you could save for yourself as well in a tax beneficial way. And you take a campus, and you have 700 people going through a program that’s a year long.

It’s not just about re-skilling, it’s about reframing their life. Re-imagining what’s next. It’s part of the reason I created MEA with my co-founders, Jeff Hamaoui and Christine Sperber, because I really felt more than anything that higher education has been way too focused on that young person. We need a midlife pit stop. We used to fuel up at age 20, got all that knowledge in our head and then started driving our car of life and then around 50 we were driving on fumes. But that was okay because maybe we would retire at 55 or at 60, and maybe we’d die at 65. But the bottom line is today, we need a midlife pit stop and a fuel up.

SAFIAN: Now you said the average age of the folks who’ve been through the program is 54, but some are coming to this at younger ages. Does that surprise you when that starts happening?

CONLEY: We have over 3,000 alums now from 42 countries around the world, and the big surprise is they are as young as 28 and as old as 88. And 15% of our alums are millennials. It’s surprising that millennials would come to a school called the Modern Elder Academy, but if you are a professional athlete, and you’re 35 years old, you are an elder. If you’re a software engineer in Silicon Valley, and you’re 40, you’re over the hill. If you’re an advertising exec on Madison Avenue, you’re probably over the hill in your 40s. So we have people coming not just because they feel like they need to press the reset button on their career, but also because we’re a wisdom school.

At any age we can reframe our relationship with aging. It’s interesting that in the Bay Area, you have old growth redwood forests, and everybody marvels at the tallest ones. But who’s marveling at the old growth humans? I think that that’s part of our shift that we have to make in our mindset on aging. And Yale’s Dr. Beck Levy has shown that when we shift our mindset on aging from negative to positive, we gain seven and a half years of additional life, which is more additional life than if we stop smoking at 50 or started exercising at 50. So where are the public service announcements for helping people feel that aging could be aspirational?

SAFIAN: I guess that’s what we’re doing here today.


SAFIAN: Before the break we heard Chip Conley, founder of Joie de Vivre hotels and the Modern Elder Academy, talk about the rise of “wisdom workers” and the rising need for a midlife pitstop.

Now he talks about his inner turmoil over the demands of scaling, the importance of community amid challenges, and his own suicide thoughts earlier on in his entrepreneurial journey.

Plus he shares leadership insights about switching from the “can do it” guy to “the conduit,” about filling a consumer need vs a social need, and about how entrepreneurs can find fulfillment.  

A note to our listeners: This next segment discusses suicide. If you or someone you know is experiencing mental health challenges, help is available.

Are we destined to hit a midlife crisis at some point? 

CONLEY: So the U-Curve of happiness, social science research shows that around 45 to 50, we do have our lowest point of happiness in life, but it’s not necessarily a crisis as much as it is a midlife calling to actually reimagine something new for ourselves. And that’s what MEA is all about. We’re opening two campuses here, one in 2024, one in 2025. That will actually be taking all of what we’ve done and growing it by tenfold.

Chip Conley on the future of Modern Elder Academy

SAFIAN: You’ve sort of gone back and forth about having multiple physical locations for MEA. There’s the hub in Baja, you talked about expanding, then you pull back, then it’s back on your agenda. What happened in that trajectory?

CONLEY: So I’ve been a for-profit entrepreneur most of my life, but now I’m a social entrepreneur. And so instead of trying to find the consumer-need and fill it, I’m now trying to find the society-need and fill it. I want to scale this thing. I want it to be as big as possible while not losing its soul. Joe Gebbia and I always would talk about this at Airbnb, but scale versus soul. I live 10-minute walk up the beach from the campus. Imagine I could be doing that. At 82, I could be walking down the beach and just teaching and then walking back.

That sounds pretty damn good. But as we’ve had more and more companies come to us and say, “We would like to do an MEA leadership Wisdom Academy,” or the United Nations says, “Will you help us on what we’re doing with ‘this is the decade of healthy aging?’” I sometimes have to say, like, do I say no? I might want to say, let’s keep it small and mighty, or do we take it to the next step and say, this is going to impact more people if we do this. So Bob, it’s a little … I’m a little confused by it. I don’t know what to do other than to say I need to surround myself with really amazing people to support me in this process. I have started to realize I’m no longer the can do it guy.

I’m the conduit guy. Hopefully things channel through me based upon the wonderful people I have surrounding me.

SAFIAN: You’ve also begun launching what you call “regenerative communities.” How do they fit in?

CONLEY: Our regenerative communities are another disruption. Who the heck wants to go live in a retirement community someday? So we’re creating these regenerative communities. Jeff Hamaoui created the first one in Baja. It’s not a commune, it’s not a cult, it’s nothing like that. But it’s people who have a common ethos, and they love the idea of a potluck every Saturday night. They love the idea of going into the farm that they’re living on and picking things for a meal and having meditation sessions each morning and things like that.

Whether it’s the Blue Zones research that Dan Butner did, or it’s the Harvard Longitudinal Study of Adult Development. Or it is Dr. Phil Pizzo’s work at Stanford.

All three of them have shown that the most important variable for living a good long life is community. It’s your social relations. We have property and liability insurance for a rainy day for our home, but where’s our emotional insurance for a rainy day in our own lives?

SAFIAN: This community imperative isn’t just for people of a certain age, right? 

CONLEY: The loneliness epidemic is true at virtually every age. But the people who actually feel the most alone and often the most lost are people in their 40s. And it is in their forties where they realize they have been running on the treadmill, they have a lot of spinning plates. They don’t have time for relations. Other than if they have a spouse.

So what the community of MEA is all about is to create 26 regional chapters. We’ve had 220 events this year within our 26 regional chapters that are global.

And so that’s an opportunity for people not just to come together and feel nice being with people who have a common ethos, but to actually build businesses together. To find a partner to get married to. Often, sometimes a second marriage for our demographic.

What’s at stake for Modern Elder Academy?

SAFIAN: So what’s at stake for MEA, for Modern Elder Academy right now?

CONLEY: I’m the sole investor in the business right now, although we are going to raise some money in 2023. I am the CEO. I am teaching a lot.

I am the center of the universe of this thing. And how do we shift that some? How do we organizationally and culturally make that shift?

What’s at stake more broadly is, I want us to help create a world where I don’t have five friends in midlife, as was true in the Great Recession, take their own lives. And I had my own suicide ideation at that same time. It’s part of the reason I decided to sell my company.

I lost five friends, all men, aged 42 to 52 — three of them entrepreneurs. Because in most cases, their net worth was their self-worth. Their sense of their business card defined who they were. And when their business fell apart, they didn’t have much to fall back on.

So part of what’s at stake is truly helping people who are often feeling like they’re suffering alone, in the middle of their life, when in fact many of the transitions they’re going through are normal transitions. Certainly for women, menopause. For men, andropause. But parents passing away, sandwich generations, taking care of parents, taking care of kids at the same time, empty nest, et cetera. There’s a lot that happens during that era.

We as a society have done a great job of putting energy into adolescents, a word that didn’t exist until 1904. We’ve spent very little time on middle-escents, a word that’s been only coined in the last 20 years.

SAFIAN: It’s this inflection point, as you say, as we head toward this second half of adulthood, which we’re not particularly emotionally or culturally prepared to deal with.

CONLEY: Where’s the roadmap? When you’re a 14 year old, there’s a roadmap, and there’s school counselors, and there’s classes, and there’s your parents, and then there’s college applications. And you’re sort of funneled through a system.

But we live in a much more freeform world at MEA. There’s a roadmap. And it’s a roadmap that allows you at whatever age, to say, “I’m going to try something new. I’m going to go back and get a Masters in something because I want to teach. I’m going to start a business.”

The data from the Kauffman Foundation’s pretty conclusive. Older people are starting 25% of the businesses in the U.S. today, and they have twice as high of a success ratio as compared to someone in their 20s.

So there’s a lot of opportunities. But we want to be on the forefront of helping people to see that people in midlife and later have more choices than they think they do.

SAFIAN: Chip, this has been great. Do you have any final thoughts for our audience?

CONLEY: I think the biggest thing Silicon Valley could be doing right now is to create matchmaking technology of modern elders and brilliant technologists all over the world. It’s a yin and a yang that this modern elder knows this, but wants to learn that. This young technologist knows that, but wants to learn this, and that you put the two of them together, and it is a synergistic relationship. So I’m not setting that up, but one of you in the audience, I hope you’ll set something like that up.

SAFIAN: Well, we’ll see if anyone picks up the torch. Thanks again for doing this.

CONLEY: Thank you for having me.

Masters of Scale’s mission is to democratize entrepreneurship. Launched in 2017 as a weekly podcast featuring Reid Hoffman, we’re now two weekly podcasts — Masters of Scale with Reid Hoffman, and Masters of Scale: Rapid Response, hosted by Bob Safian — as well as an award-winning daily learning app, a best-selling book, virtual and live events, and more, serving a global community of founders, funders, and leaders looking to innovate at scale.
Sign up for our weekly newsletter