Chip Conley

I used to think the whole “age is just a number” line was a bit of a cop-out, an empty cliché. Not so much anymore. And I can thank Satchel Page, a pitcher from the Negro Baseball League. Satchel was recruited to join the Cleveland Indians soon after Jackie Robinson became the first black Major Leaguer. Paige became the oldest rookie in Major League history at age 42, even though he wasn’t sure of his actual age. It was a good thing, too. Paige continued...

We learn in our teens. We earn in our twenties. We yearn in our thirties. We burn in our forties. We discern in our fifties. And, we adjourn in our sixties. But, what if we lived life as a mash-up? Maybe we ought to “unlearn and return” to new subjects and experiences throughout life. Live by the “learn, earn, yearn, burn” rule and I promise you heartburn and a midlife crisis. The Game of Life was created by Milton Bradley in 1860. Isn’t it time you deviated from that linear, one-size-fits-all board game?

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.

In 2018, I went scuba diving in Indonesia with my then 80-year-old dad. One morning before our first dive, I took an online longevity quiz that said I’d likely live to 98-years-old. I asked my dad how long he thought he’d live. He mused for a moment, and then to my great surprise, said, “98!” What’s miraculous about that is...

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).

Want to see what massive change looks like? Check out the table below, which depicts how economic power has evolved in the U.S. from an industrial to a high-tech economy. No surprise, right? What is a surprise is how little we are prepared for that change. How does learning keep up? More accurately, where do people repurpose themselves to keep up with the changing times? “Life-long learning” may be a trendy phrase, but they’re hollow words without a home.

A wise person can distill down the essence of a business or a person’s mastery. Long ago, we created an exercise in my boutique hotel company, Joie de Vivre, in which we asked management theorist Peter Drucker’s favorite question, “What business are we in?” five times in sets of dyads (you sit two people facing each other). The value of this repeating question meant the answerer, who couldn’t repeat an answer, needed to act like a miner in digging deeper into what’s their core differentiator. This approach led us to discover...

In most circles, it’s almost impossible to talk about getting older without the conversation turning to retirement, and questions of “when, where, and how.” Of course, no one stops to ask why. The “why” is built into what we’ve been taught our final act should look like—the promised pot of gold at the end of the rainbow. Retire is what you do when you reach a certain age—stop working, slow down, and take it easy. And if you can’t afford this dream, it’s easy to feel like you’ve been cheated, or you’re a failure.

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.