Modern Elder

I’m beginning to think I should have renamed my recent book, “Wisdom@Work: The Making of a Modern Elder,” with “How Boomers Boo-Boo With Millennials.” How often have we seen older workers lecture younger workers on how the world works? The irony is that nearly 70% of those in their mid-50s have a boss younger than them today.

I was honored to be the finale speaker at the annual TEDxMarin a couple months ago. The video was just published and offers answers to some of the following provocative questions: What are the three 20th century life stage inventions and why hasn’t midlife been given the same public policy attention as the other two?

I loved spending nearly 90 minutes on stage with Brian Chesky at the Commonwealth Club almost exactly a year ago. It was a wonderful opportunity to show in public how we’ve operated in private over the past six and a half years. One of the things we discussed was the disadvantage of being a young entrepreneur. Brian suggests that...

Wisdom is about pattern recognition. It’s time for investors to recognize a pattern that is destroying value and making a mess of companies. The start-up game isn’t the same as the keep-it-up game. Start-ups are full of idealism and chutzpah, charisma and hubris. But, these blitzkrieg tactics wear thin when the keep-it-up game requires diplomacy with regulators, humility with competitors and clients, empathy with employees, and stamina to run further than a start-up sprint.

During my time at Airbnb, I recognized a new kind of elder emerging in the workplace. Not the traditional elder of the past, regarded with reverence simply for years lived. But a Modern Elder, striking into new territory due to the growing value of their relevance: the ability to use timeless wisdom to address modern day problems. By understanding the importance of context, today’s Modern Elder is the perfect alchemy of curiosity and wisdom (curiosity to open up possibilities and wisdom to distill down what is essential).

“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.