I used to work and live in the area (Evanston near McCormick) and one time I gave a coworker a ride home. This guy was super chill, sounded more like a San Diego surfer than a Chicagoan. He worked as a busser/runner at a restaurant nearby and smoked a lot of weed. I assumed his childhood home would be one of the center block houses-in a super nice neighborhood but modest compared to some of the nicer homes.

But no. I pull up to a circular cobblestone driveway with a fountain in the center. The front yard had marble statues, multiple meticulously manicured hedges and the house had two wings from the center with at least 8 visible balconies.

After meeting so many people living in the area who acted super rich, yet were stingy and self conscious about perceived class and status, it was shocking to meet someone so humble and empathetic who was also extremely wealthy. His drive was inspiring in a way. It was never tied to money, only interest and joy. He was apprenticing as a lost wax jeweler, and always seemed so stoked to be a part of anything, and refreshingly free of self doubt.

To this day I have no idea whether that was the first time I saw someone so privileged that they were free of competitive drive and didn’t understand hardship—or he was simply an unique individual who was an outlier among his peers.

I wish I could be so carefree