First off, congrats to the 2019 World Series champs, the Washington Nationals, the oldest team (age-wise) in the Major Leagues! Nice way to celebrate my birthday today, Halloween. Elders still know how to get in the groove! Why is the owl perceived as the wisest animal in the kingdom?

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.

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.

Context is everything. The rule of thumb for social media videos is to keep them less than 2 minutes. And, yet, there’s a plethora of podcasters aping my friend Tim Ferriss whose interviews are nearly 2 hours. If you have a message, understand the context. Empathize with the recipient. It's Monday: that’s why I’m gonna keep this one short. LOL.

Life used to be so simple. We learned till our early 20s, earned till our mid-60s, and then retired happily to our La-Z Boy. We paid our dues early in our career so we could coast with our three-martini lunches (especially if we were male and pale). Society’s outdated three-stage model (learn, earn, retire) taught us...

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...