Wisdom

Lost and clueless. That’s what I felt six months after I launched my boutique hotel company at age 26. I had quickly renovated the “no-tell motel” we’d bought in a dodgy San Francisco neighborhood—partly due to my putting a beer keg in the courtyard each weekend, so my friends would come over and help paint the place (learned a thing or two from Tom Sawyer).

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.

Jaws drop when I answer the question, “What’s your favorite leadership book of all-time?” Improbably, I consistently answer, “Man’s Search for Meaning” by Viktor Frankl. What does this rumination on life inside a Nazi concentration camp written by a psychologist have to do with leadership? Frankl chronicles how meaning can be the fuel for life even in the most challenging of situations. He articulates that character can overcome circumstances, which is an extremely valuable lesson for leaders.

“Juxtaposition” is one of my favorite words. It suggests maximum possibility through the attraction of opposites—what happens when two separate elements join together to create magic and power. Laurel and Hardy. Laverne and Shirley. Harold and Maude. Tony Bennett and Lady Gaga. Call it Modern Day Alchemy—turning lead into gold, or better yet, transforming opposing ideas into order, meaning, and beauty.