So, tone and intent need to weave in empathy. I found many of the Why questions I asked at Airbnb helped us to occasionally see both our blind spots and our mission.

In the spirit of wise people mixing gravitas with levity, here are ten Why questions on my mind today regarding the subject of aging in the modern world:

• Why isn’t the Fountain of Wisdom as popular as the Fountain of Youth?

• Why can’t life be more like a video game in which I “level-up” (rather than age) as I become more proficient at understanding how to live on Earth (a game in which we focus on our stage of life, not our age)?

• Why can’t we adopt the airline’s approach to earning loyalty points for “mile-age” as I’ve lived a lot of miles in my age?

• Why do I have “age amnesia,” often thinking I’m 20 years younger than I am, until I see my impromptu photo on Facebook?

• Why do they ask me to drink more water as I get older, just when I seem to have to pee every 15 minutes?

• Why do I need reading glasses just when my vision for life and myself is only getting better?

• Why do we call the bathroom the “John” when it would feel so much better calling it the “Jim” (trips to the potty imagined as a workout)?

• Why do we need to deliver emails on Sundays, especially in an era in which we’re all working at home and work and leisure life is so blended? Can’t we have a day off from the email pollution?

• Why are almost all of the radical longevity advocates (those who want to live forever) men when, in fact, men live almost 10% shorter lives than women?

• Why do so many people want to trade-in an old soul for a young body?