When it comes to power in the workplace, 30 is the new 50

We’re in the midst of two tectonic demographic shifts in the workplace that, at first glance, seem to be at odds with each other. We’re living longer and working longer–either by choice or necessity (it’s hard to finance a 30-year retirement with a 40-year career). The fastest-growing age demographic of employees in the workplace is 65 and older, which has experienced a 35% jump in numbers over the past half-decade. In fact, nearly half of the age-demographic increase in the number of people participating in the U.S. labor force between 2016 and 2026 is attributable to those 60 and older. So, many of us are surprised today to find ourselves at midlife and mid-career.

At the same time, there’s such a growing reliance on DQ (digital intelligence) that companies are desperate to hire and promote digital natives. Nearly 40% of Americans now report to a younger boss, and this will become the majority by 2025. Seven of the 10 most valuable companies in the world today are tech companies. The average employee age at giants like Facebook, Apple, and Google isn’t quite 30. And we’re seeing startup entrepreneurs in their early 20s become global disruption billionaires before they turn 30. Sixty may be the new 40 physically, but when it comes to power in the modern workplace, 30 is the new 50.

Some like to portray this as a generational war now that we have five generations in the workplace for the first time. I beg to differ. Because, based upon my experience over the past half-dozen years, I’ve seen how a symbiotic relationship between generations can be created–like an intergenerational potluck–to take companies to great heights.


After selling my boutique hotel company, Joie de Vivre, around my 50th birthday at the bottom of the Great Recession, I wasn’t sure what was next for me. In the film The Intern, Robert De Niro’s character suggests, “Musicians don’t retire, they quit when there’s no more music left inside of them.” I knew I still had music left to share, but I wasn’t sure who wanted to riff with me. That’s about the time when Airbnb cofounder and CEO Brian Chesky approached me to help turn his fast-growing tech startup into a global hospitality brand, as their head of global hospitality and strategy, and Brian’s in-house mentor.

Sounded good. But I was an “old-school” hotel guy and had never used Airbnb. I didn’t even have an Uber or Lyft app on my phone in early 2013 I was 52 years old, I’d never worked in a tech company, and I was twice the age of their average employee. And, after running my own company for well over two decades, I’d be reporting to a smart guy who was 21 years my junior. I was a little intimidated. But I took the job and, as Brian has described recently, we developed “one neural network between the two of us.” We were able to combine Brian’s impressive design skills and visionary leadership with my “know-how” and “know-who” of the hotel industry to turn home sharing from a peripheral to a mainstream part of the hospitality sector.

Additionally, with my Director of Hospitality Laura Hughes Modi, who was a quarter-century younger than me, and our smart data science team, we took on evolving Airbnb’s peer-to-peer review system, using Laura’s analytical mind and my human-centered intuition. Together, we were able to create an instantaneous feedback loop that helped improve our hosts’ understanding about what was most important to our guests. Now Airbnb’s guest satisfaction scores are higher than the hotel industry’s. High-tech meets high-touch. My four years as a full-time leader and two years now as a part-time strategic adviser proved to me that opening up the pipelines of intergenerational wisdom in the modern workplace is the essential trade agreement for our times.

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My experience was fortunate as I was tapped on the shoulder by the Airbnb founders. That’s not the norm; many young leaders don’t know how to find experienced talent, as many wise middle age managers are invisible to this world. So if you’re starting to feel a little irrelevant, how do you shift your mind-set to repurpose yourself in this new environment? I believe there are four steps that outline the path to becoming what I call a modern elder, someone who is as curious as they are wise.