I bike to Pilsen in the morning Saturday. Avi opens the door as I’m walking up. I follow him upstairs. I’m here to help Sophie with her art school applications. I met her when she was five or so. Time flies.

Her mom, Wendy, and I went to art school together at the beginning of the 90s. Wendy was going to be a painter like me. We were on the same horrible floor of the Herman Crown Center dorm at Roosevelt University reserved for SAIC students. Then we lost touch.

A couple years into the Chicago leg of my cab career, I picked Wendy up randomly. We hadn’t seen one another in twenty years. She was now a flamenco dancer with a small daughter. We hung out a few times. I met Sophie. Wendy asked me to decorate some lunch bags for her.

Some time later, Wendy called up and asked if I’d be willing to give Sophie art lessons. I’d had a few isolated experiences with teaching, but nothing substantial. I hesitated. My feelings about how art is taught are pretty complicated. Depending on the day you catch me, I may say it’s impossible to teach art; then, on another day, I might be more hopeful about it. Wendy somehow talked me into it.

At around ten years old, Sophie already had her own art ego and personality. My job was to suggest some exercises but mostly to stay the fuck out of the way. One of the big hazards of art teaching is imposing one’s own personality with all its flaws on your students. There are many damaged people in classrooms trying to mend their own damage by manufacturing little carbon-copy acolytes. The last thing I wanted was to have Sophie reflect me back to myself as a result of something I’d shown her.

I needn’t have worried. She pushed back and resisted my lessons, just as I had when I was her age. It warmed my heart. Every artist runs their own race. No one can do your work but you, for better and worse.

I think back to an Amtrak trip to Chicago in the late 80s. My first visit to the city I didn’t know then that I’d call home. The sheet of slides of high school artwork I kept taking out as the train went west. I was convinced there was dust on the slides that would prevent the people at SAIC from making out the quality of my work. When that time came, the woman put the sheet up to the light for all of five seconds, then went back to pitching the school to me.

Sitting on the back deck of her family’s apartment in Pilsen, Sophie shows me her half-completed application essay. Over the past decade-plus, I’ve edited many pieces of text for her mother. Grant applications, art statements, you name it. This feels similar. I try my best to talk Sophie out of going to SAIC. Tell her to ignore whatever reputation these institutions purportedly have. To concentrate on finding teachers and facilities that can expand her skills, rather than go for name-recognition or prestige. Tell her how, thirty years on, I’m still not convinced going to art school was worthwile.

I tell her I think she’ll always make art, no matter what degree she gets. She liked hearing that. It’s remarkable to me that a young person today would want to dedicate herself to making marks on paper and canvas, just like I did once.

Maybe I shouldn’t be surprised. It felt like I was about a century late when I started out. What’s a few more added decades matter? We’ve been doing this thing since we lived in caves. Odds are, we’ll still be at it when we’re forced back into caves or whatever survival bunkers are in our near future.