Chip Conley

“From our sixties onward, let’s enjoy being stylish once again!” So, proclaims one of Japan’s hottest new magazines targeting women over 60. Japan has a variety of new magazines targeting “the nice generation” (as chronicled by Monocle magazine).

Warning: this next sentence is bawdy. In an episode of The Simpsons, when Marge was about to board a ship, Smithers said, “'I think women and seamen don't mix." Of course, double entendres have been with us for centuries. Even Shakespeare used them in “Romeo and Juliet” (Google “bawdy hand”).

“Freed from the yolk of ambition and responsibility, released from the hunger of destiny, the elderly have time for themselves….old age is the embryonic phase of the afterlife.”

“This has not been a happy year. This is not a happy country.” I wrote those words in 2008. Of course, they’re even more relevant today. A dozen years ago, I decided to venture to Bhutan to study their Gross National Happiness index.

I find progressions fascinating. It’s probably why I’m obsessed with our life stages: childhood, adolescence, adulthood, middlescence, elderhood. I also love the progressions of the four seasons, which can be a perfect metaphor for life.

What would be your ideal title when you’re 50+? I was connecting with a friend who I’ve had the pleasure of working with both at Joie de Vivre and Airbnb and she was telling me about a recent conversation she had with the “Resident Wise Woman” Deb Ryan of the Tahoe Truckee Community Foundation (scroll down to the second row of leaders to find Deb).

I got my real estate license while in college at age 19. I was subsequently hired to work for my uncle’s commercial real estate brokerage firm in 1980, at a time when Silicon Valley was primarily fruit trees and vacant land.

In my mid-twenties, I told a friend I was going to the Esalen Institute to “find myself.” He responded matter-of-factly, “You’re out of luck. You won’t find yourself there because I see you’re here.” Clearly, my friend didn’t get what I meant.

Diane Flynn and Patty White are co-conspirators of mine and they’re popular MEA guest faculty. Their book, “The Upside,” showcases the business case for gender diversity and specific actions each stakeholder can take to build more inclusive cultures.

I was once called “the daring crossing guard at the treacherous intersection of psychology and business.” Someday, I hope to walk on stage for a speech with a day-glow orange vest and STOP sign. No doubt, having a sense of humor reacquaints us with our humanity.