Intergenerational Collaboration

Steve Jobs and I share one thing in common beyond our round glasses. We’re both big fans of Stewart Brand, the founder of the Whole Earth Catalog. One of my guiding lessons, when I was an entrepreneur in my mid-twenties, came from Stewart. He suggested a key tenet in starting a business is to “keep it cheap, small, and local” because it allows you to reduce the size of your mistakes and learn from them.

The meme of the moment was accelerated by this New York Times article marking the end of friendly generational relations. Beyond the fact that the old cranky dude preaching in the TikTok video doesn’t vaguely resemble a Modern Elder who is as curious as they are wise, let’s accept that it was Boomers who created the original “generation gap” in the 1960s.

My favorite business article of 2019 (so far) was in the MIT Sloan Management Review with the same title as this post and the subtitle of “How Management Style Varies With Age.” This is a perfect segue after my riff yesterday about how young founders, who often have deep but narrow technical skills and fresh eyes for disruption, could be paired with seasoned leaders who are usually more adept at interpersonal collaboration and focusing on the big picture.

How often do you get a couple of leaders—one a Millennial, one a Boomer—on stage talking about the definition of wisdom? This short video of Airbnb CEO Brian Chesky and me will offer you a few of the ingredients of wisdom: good judgment, pattern recognition, curiosity, the perfect alchemy of confidence and doubt, willingness to seek guidance from those more experienced, and understanding the collateral consequences of your actions or decisions. Hope you enjoy.