Chip Conley
2,662,989 views • 12:22

It was my third day on the job at a hot Silicon Valley start-up in early 2013. I was twice the age of the dozen engineers in the room. I'd been brought in to the company because I was a seasoned expert in my field, but in this particular room, I felt like a newbie amongst the tech geniuses. I was listening to them talk and thinking that the best thing I could do was be invisible. And then suddenly, the 25-year-old wizard leading the meeting stared at me and asked, "If you shipped a feature and no one used it, did it really ship?"


"Ship a feature"? In that moment, Chip knew he was in deep ship.


I had no idea what he was talking about. I just sat there awkwardly, and mercifully, he moved on to someone else. I slid down in my chair, and I couldn't wait for that meeting to end.

That was my introduction to Airbnb. I was asked and invited by the three millennial cofounders to join their company to help them take their fast-growing tech start-up and turn it into a global hospitality brand, as well as to be the in-house mentor for CEO Brian Chesky. Now, I'd spent from age 26 to 52 being a boutique hotel entrepreneur, and so I guess I'd learned a few things along the way and accumulated some hospitality knowledge. But after my first week, I realized that the brave new home-sharing world didn't need much of my old-school bricks-and-mortar hotel insights. A stark reality rocked me: What do I have to offer? I'd never been in a tech company before. Five and a half years ago, I had never heard of the "sharing economy," nor did I have an Uber or Lyft app on my phone. This was not my natural habitat.

So, I decided at that moment that I could either run for the hills, or cast judgment on these young geniuses, or instead, turn the judgment into curiosity and actually see if I could match my wise eyes with their fresh eyes. I fancied myself a modern Margaret Mead amongst the millennials, and I quickly learned that I had as much to offer them as they did to me.

The more I've seen and learned about our respective generations, the more I realize that we often don't trust each other enough to actually share our respective wisdom. We may share a border, but we don't necessarily trust each other enough to share that respective wisdom. I believe, looking at the modern workplace, that the trade agreement of our time is opening up these intergenerational pipelines of wisdom so that we can all learn from each other.

Almost 40 percent of us in the United States have a boss that's younger than us, and that number is growing quickly. Power is cascading to the young like never before because of our increasing reliance on DQ: digital intelligence. We're seeing young founders of companies in their early 20s scale them up to global giants by the time they get to 30, and yet, we expect these young digital leaders to somehow miraculously embody the relationship wisdoms we older workers have had decades to learn.

It's hard to microwave your emotional intelligence. There's ample evidence that gender- and ethnically diverse companies are more effective. But what about age? This is a very important question, because for the first time ever, we have five generations in the workplace at the same time, unintentionally. Maybe it's time we got a little more intentional about how we work collectively. There have been a number of European studies that have shown that age-diverse teams are more effective and successful. So why is that only eight percent of the companies that have a diversity and inclusion program have actually expanded that strategy to include age as just as important of a demographic as gender or race? Maybe they didn't get the memo: the world is getting older!

One of the paradoxes of our time is that baby boomers are more vibrant and healthy longer into life, we're actually working later into life, and yet we're feeling less and less relevant. Some of us feel like a carton of milk — an old carton of milk — with an expiration date stamped on our wrinkled foreheads. For many of us in midlife, this isn't just a feeling, it is a harsh reality, when we suddenly lose our job and the phone stops ringing. For many of us, justifiably, we worry that people see our experience as a liability, not an asset. You've heard of the old phrase — or maybe the relatively new phrase — "Sixty is the new forty, physically." Right? When it comes to power in the workplace today, 30 is the new 50. All right, well, this is all pretty exciting, right?


Truthfully, power is moving 10 years younger. We're all going to live 10 years longer. Do the math. Society has created a new 20-year irrelevancy gap. Midlife used to be 45 to 65, but I would suggest it now stretches into a midlife marathon 40 years long, from 35 to 75. But wait — there is a bright spot. Why is it that we actually get smarter and wiser about our humanity as we age? Our physical peak may be our 20s, our financial and salary peak may be age 50, but our emotional peak is in midlife and beyond, because we have developed pattern recognition about ourselves and others.

So how can we get companies to tap into that wisdom of the midlife folks, just as they nurture their digital young geniuses as well? The most successful companies today and in the future will actually learn how to create a powerful alchemy of the two.

Here's how the alchemy worked for me at Airbnb: I was assigned a young, smart partner, who helped me develop a hospitality department. Early on, Laura Hughes could see that I was a little lost in this habitat, so she often sat right next to me in meetings so she could be my tech translator, and I could write her notes and she could tell me, "That's what that means." Laura was 27 years old, she'd worked for Google for four years and then for a year and a half at Airbnb when I met her. Like many of her millennial cohorts, she had actually grown into a managerial role before she'd gotten any formal leadership training. I don't care if you're in the B-to-B world, the B-to-C world, the C-to-C world or the A-to-Z world, business is fundamentally H-to-H: human to human. And yet, Laura's approach to leadership was really formed in the technocratic world, and it was purely metric driven. One of the things she said to me in the first few months was, "I love the fact that your approach to leadership is to create a compelling vision that becomes a North Star for us."

Now, my fact knowledge, as in, how many rooms a maid cleans in an eight-hour shift, might not be all that important in a home-sharing world. My process knowledge of "How do you get things done?" based upon understanding the underlying motivations of everybody in the room, was incredibly valuable, in a company where most people didn't have a lot of organizational experience. As I spent more time at Airbnb, I realized it's possible a new kind of elder was emerging in the workplace. Not the elder of the past, who actually was regarded with reverence. No, what is striking about the modern elder is their relevance, their ability to use timeless wisdom and apply it to modern-day problems.

Maybe it's time we actually valued wisdom as much as we do disruption. And maybe it's time — not just maybe, it is time — for us to definitely reclaim the word "elder" and give it a modern twist. The modern elder is as much an intern as they are a mentor, because they realize, in a world that is changing so quickly, their beginners' mind and their catalytic curiosity is a life-affirming elixir, not just for themselves but for everyone around them. Intergenerational improv has been known in music and the arts: think Tony Bennett and Lady Gaga or Wynton Marsalis and the Young Stars of Jazz. This kind of riffing in the business world is often called "mutual mentorship": millennial DQ for Gen X and boomer EQ.

I got to experience that kind of intergenerational reciprocity with Laura and our stellar data science team when we were actually remaking and evolving the Airbnb peer-to-peer review system, using Laura's analytical mind and my human-centered intuition. With that perfect alchemy of algorithm and people wisdom, we were able to create and instantaneous feedback loop that helped our hosts better understand the needs of our guests. High tech meets high touch. At Airbnb, I also learned as a modern elder that my role was to intern publicly and mentor privately. Search engines are brilliant at giving you an answer, but a wise, sage guide can offer you just the right question. Google does not understand, at least not yet, nuance like a finely attuned human heart and mind. Over time, to my surprise, dozens and dozens of young employees at Airbnb sought me out for private mentoring sessions. But in reality, we were often just mentoring each other.

In sum, CEO Brian Chesky brought me in for my industry knowledge, but what I really offered was my well-earned wisdom. Maybe it's time we retire the term "knowledge worker" and replaced it with "wisdom worker." We have five generations in the workplace today, and we can operate like separate isolationist countries, or we can actually start to find a way to bridge these generational borders. And it's time for us to actually look at how to change up the physics of wisdom so it actually flows in both directions, from old to young and from young to old.

How can you apply this in your own life? Personally, who can you reach out to to create a mutual mentorship relationship? And organizationally, how can you create the conditions to foster an intergenerational flow of wisdom? This is the new sharing economy.

Thank you.