Learning the Ropes Later in Life

(This essay is the fifth in the Milken Institute Center for the Future of Aging series, The Business of Aging, running on Next Avenue weekly over the next few months. The essays are a companion piece to the center’s new report,  Silver to Gold: The Business of Aging.)

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A growing number of people feel like an old carton of milk, with an expiration date stamped on their wrinkled foreheads. One paradox of our time is that boomers enjoy better health than ever, remain young and stay in the workplace longer, but feel less and less relevant. They worry that bosses or potential employers may see their age more as a liability than an asset. Yet we workers “of a certain age” are less like a carton of milk and more like a bottle of fine wine — especially now, in the digital era.

I started a boutique hotel company when I was 26 and after 24 years as CEO, sold the company. That’s when Airbnb came calling. In early 2013, co-founder and CEO Brian Chesky and his two millennial co-founders asked me to help turn their growing tech startup into a hospitality giant, as their head of global hospitality and strategy. Sounded good.

But I was an “old school” hotel guy and had never used Airbnb. I didn’t have an Uber or Lyft app on my phone. I was 52 years old, I’d never worked in a tech company, I was twice the age of the average Airbnb employee, and, after running my own company for well over two decades, I’d be reporting to a smart guy 21 years my junior.

I was a little intimidated. But I took the job.

On my first day, I heard an existential tech question in a meeting and didn’t know how to answer it: “If you shipped a feature and no one used it, did it really ship?” Bewildered, I realized I was in deep “ship,” as I didn’t know what it meant to “ship product.”

Brian had asked me to be his mentor, but I also felt like an intern. I realized I’d have to figure out a way to be both.

First, I quickly learned that I needed to evolve my historical work identity.

The company didn’t need two CEOs, or me pontificating wisdom from the elder’s pulpit. More than anything, I listened and watched intently like a cultural anthropologist, intrigued by this new habitat. Often, I would leave a meeting and discreetly ask one of my fellow leaders, who might be two decades younger than I was, if he or she was open to some private feedback on how to read the emotions in the room a little more effectively.

My next lesson can be summarized in a one-line trade agreement: “I’ll offer you some emotional intelligence for your digital intelligence.”

Many young people can read the face of their iPhone better than the face of the person sitting next to them. I was surrounded by folks who were tech-savvy — but were perhaps unaware that being “emo-savvy” could be just the thing to help them grow into great leaders.

I realized that we expect young digital-era leaders to miraculously embody relationship wisdom, with very little training, that we elders had twice as long to learn. Over time, I learned how to intern publicly and mentor privately.

I also reconceived my bewilderment as curiosity and gave free rein to it.

I asked a lot of “why” and “what if” questions, forsaking the “what” and “how” questions on which most senior leaders focus. My beginner’s mind helped us see our blind spots a little better. Paradoxically, this curiosity kept me feeling young.

Management theorist Peter Drucker was famously curious. He lived to 95, and one of the ways he thrived later in life was by diving deeply into a new subject that intrigued him, from Japanese flower arranging to medieval war strategy.

I’ve spent a lifetime being curious about people and things, which, I guess, means I’m well-read and well connected. I’m not sure there’s anyone in Airbnb who’s been asked to chat by a more diverse collection of employees. I always responded with an enthusiastic yes to these invitations because if I were to plot all of those conversations across the various islands (or departments) of the company, you’d see a rich web of relationships and knowledge.

This served me even more as a strategic adviser to the founders since I had a real sense of the pulse of the company and its various teams. And, I felt a sense of meaning being a confidante to so many.

Boomers and millennials have a lot to offer and learn from each other. Enter the “Modern Elder,” who serves and learns, as both mentor and intern, and relishes being both student and sage.

The opportunity for intergenerational learning is especially important to boomers, as we are likely to live 10 years longer than our parents, yet power in a digital society has moved 10 younger. This means boomers could experience 20 additional years of irrelevance and obsolescence.

Wisdom is about pattern recognition. And the older you are, the more patterns you’ve seen. There’s an old saying I love: "When an elder dies, it’s like a library has burned down.”

In the digital era, libraries — and elders — aren’t quite as popular as they used to be. But wisdom never grows old.