Why Ageism Should Be Included In Your DEI Strategy: The Founder Of Modern Elder Academy

For the first time ever, we have five generations together in the workplace. When we talk about DEI, it’s important to also talk about ageism and generational diversity.

In this episode of Breaking the Bias, Consciously Unbiased founder Ashish Kaushal sits down with Chip Conley, founder & CEO of Modern Elder Academy. Just a little about Chip: At age 26, Chip grew a successful boutique hotel company and later became a best-selling author. Then, at 52, he joined AirBnB as the Head of Global Hospitality and Strategy, where most of the employees were half his age. Today he is promoting the idea of a “Modern Elder,” with his latest book, Wisdom at Work. He defines an elder as someone who is as curious as they are wise, and is helping to reframe aging as an opportunity for growth. 

In this episode, Chip shares how a near-death experience changed the way he lives his life, how his work at AirBnB helped him bridge generational divides, and how to hold on to a beginner mindset in midlife and beyond. 

Read on for key takeaways below, and listen to the full conversation here. 


*This is an excerpt of the Interview has been condensed for length and clarity


Ashish: Can you share your personal journey, and how a near-death experience changed how you lived your life?


Chip: “I started a boutique hotel company, one of the first boutique hotel companies in the United States in the mid-1980s when I was 26 years old. It was called Joie de Vivre and was based in San Francisco. We had 52 boutique hotels, each with their own name, around the state of California. 

I loved it for 22 years. Then my last two years, I hated it and I didn’t want to do it anymore. Everything that could go wrong was going wrong in my life. And I was in essence having a little bit of a midlife crisis—which I now call a midlife chrysalis. I think I was in the dark and gooey cocoon in between caterpillar and butterfly. Long story short, I had a NDE (near death experience)…That experience woke me up and I said, ‘Do I want to continue to live my life this way?’ 

It’s not a bad way to look at your life on a daily basis—although you don’t want to make decisions based upon one bad day, one bad week, or even one bad month. But what I knew for sure was that I had outgrown the identity that was firmly implanted on my body. I needed to do something new and to reimagine and repurpose myself. So that led me to selling my company at the bottom of the Great Recession, which led me to being open to seeing what was next in my early fifties. That’s when I got a call from the three founders of Airbnb 10 years ago when nobody had ever heard of Airbnb.

They were a small tech startup in San Francisco. They said, ‘Listen, you are a hospitality entrepreneur who knows the travel industry well and has run companies. Will you come and help be our in-house mentor?’ I did that for seven and a half years, and then for three and a half years as a strategic advisor. So I saw the worst side of midlife when I was going through my bad period. Then I saw my best part of midlife, which is in my fifties when I saw how you can be relevant and how intergenerational collaboration in the workplace can be incredibly energizing. So that’s my story: I know that midlife can be bad. I also know that it can be good.”

Related: Ageism: Unlocking The Power Of The Multigenerational Workforce

Ashish: How has your definition of success evolved as an elder compared to your younger days?


Chip: “I’m a big fan of Carl Jung’s work as the famous psychologist. And, there’s a guy named Richard Rohr, who’s a famous Christian mystic and who’s come to the Modern Elder Academy as a student. Both of them said the same thing, which is that the primary operating system for the first half of our adult life is our ego. It’s what propels us forward; it’s what individuates us. It can be a very positive thing, but it also can be negative if it gets out of control. But they also both said that around midlife is when you realize that there’s a primary operating system change, and it’s moving from the ego to the soul.

Most of us have no manual for how to now drive this new operating system of the soul. What became really apparent for me is the success script that I had lived during my twenties, thirties and forties was very much ego driven. It served me well in many ways, but by the time I got to the point where I sold my company at the bottom of the Great Recession, and I didn’t want to do it anymore after having been CEO for 24 years, I realized that there was something much deeper and more meaningful I was looking for in my life. 

I can look back now and say, ‘Wow, I was having this operating system change. I’m 62 now, and for the last dozen years, success has really been more about, ‘Who am I serving and how am I serving them?’ 

Eric Erikson, the famous developmental psychologist, said, ‘I am what survives of me.’ So what will survive me? What is it that I will be able to offer to the world that is going to live beyond me? So often, so much of that is the relationships we build. For me, a lot of the success that I define today comes from who I mentor, who I support to help them be more successful in their lives.”

Related: Why Security Is An Illusion—And How The “Forgotten Generation” Can Build Wealth


Ashish: Can you share an example of something that really sticks out in your mind that you learned from a younger person at work, and a lesson you learned from an elder at work?


Chip: “When I joined Airbnb with the founders, I thought, ‘Well, they brought me in as the mentor, so I guess I’m supposed to be the wisest one. And very quickly I learned, I’m not the just the wise one, I’m also the dumb one, because I was 52 years old and I never worked in a tech company before. 

So I have learned a lot of DQ, or digital intelligence, from younger people, and especially during my time at Airbnb learning about how to create a compelling website or how to use functionality on my iPhone that I’d never used before or how to understand the customer journey when it comes to a digital relationship. So all those are things I learned from younger people.

What I’ve learned from older people and elders along the way is usually that at the end of the day…the ones you most remember and most admire are the ones who taught you character qualities. As David Brooks famously wrote in a New York Times op ed, it’s not the resume you look at, it’s what people say at your eulogy. Along the way, I’ve gotten really great advice about how to become a more emotionally intelligent leader, typically from people older than me.”

Related: Gen X Career Coaches On How To Articulate Your Value

Ashish: Do you think part of the thing that’s missing in today’s digital intelligence workplace is that we’re not tapping into the wisdom of older generations, and also sort of hiding behind this digital platform and not having that human interaction that builds a bond for creativity?


Chip:  “In the Covid era everybody’s doing things by means of video conferencing, and something gets lost. As a leader, or as an emotionally intelligent person in an organization, you need to say, ‘How do I integrate humanity back into the relationship?’ Because Zoom is a very transactional technology. That’s the first point. Number two is, yes, a lot of organizations need to look at how they develop age diversity, but this goes in both directions. It’s like old-school manufacturing companies or law firms or [where] the hierarchy tends to be top down, from old to young…They could use age diversity because those older people at those organizations might actually learn something from the younger people.

But in Silicon Valley, what’s very clear to me based upon my experience is you have these young people—often Millennials, but sometimes Gen Z—who are getting funded for huge amounts of money from venture capitalists to go create these ventures. The young people, they have a beautiful idea. They may be brilliant technologists, but they’ve never run a company before. They’ve never understood what I would call ‘process knowledge.’ How do you get things done in an organization? So there’s a lot of opportunity. 

The AirBnB founders called me the modern elder. I didn’t like that at first, but they said, ‘Chip, a modern elder is someone who’s as curious as they are wise.’ It was like, okay, if that’s what a modern elder is, I will be the modern elder here.

What they really wanted and needed was my wisdom more than anything. How do we create organizations where a young technologist says, just like Brian Chesky the CEO [of AirBnB], I need Chip to be my in-house mentor and to run certain functions of the company, even though he’s 21 years my senior and double the age of the average person in the company? He also had to have enough courage and confidence to know that he was going to continue to be CEO. My job was not to come in and take his job. He had to be humble enough to say, I want to learn a lot here.

It is often hubris that actually raises the money from venture capitalists, but it’s humility that runs the organization. So that was a beautiful experience.”




The Modern Elder Academy

Generations Over Dinner

Wisdom Well Blog