Earlier this week I had a CFCC meeting in Chicago, so I left the wife and child carless and drove 400 miles to Chicago (gas may be expensive, but it was still cheaper than planes or trains). I used to drive that stretch of Interstate between St. Paul and Detroit all the time in college (at least six times per year?), so it was just like old times. I also realized that I haven’t taken a long road trip by myself in a long time. I think 2005 was the most recent, and before that it was probably 2001. I guess marriage does that to you.

I also realized the last time I spent any considerable amount of time in Chicago was 1999 when I lived there for a summer. Welcome to nostalgia land.

But first I stopped for gas in DeForest, Wisc., and discovered a giant pink elephant with glasses and a giant cow with a veiny udder. Wisconsin rules.

The first exit for nostalgia land was Elgin, where I lived and worked for the summer of 1999. Geography has always had a strong hold on me. It’s why I love going back to Kansas even though there’s nothing to do there, and it’s why I took a photographic tour of my childhood the last time I was in Michigan. So stopping in Elgin seemed like a no-brainer (I’ve actually done it before).

First I visited Judson College, where I lived for the summer. I stayed at Volkman Hall, which was built in 1963 and resembles those craptacular hotels where the hallway is the balcony outside. It was a strange summer, the first one officially on my own. I spent many a days in the basement of that dorm watching the Simpsons by myself before making a supper of french toast or eggs. I lost weight that summer (which for me is saying a lot). I lived like a resident alien on that campus. I only lived there because I had an internship in town and Judson offered housing. My roommate was in the same boat (though he spent his evenings sidled up to the bar at TGI Fridays). I met a few people who lived there and actually went to Judson, but it was less than an acquaintance.

Next I stopped at the former offices of Real Magazine. The buildings of the office complex resemble old Pizza Huts and they haven’t changed. A few current workers were milling around outside smoking, so I didn’t want to be too much of a tourist dork. But I did sit down on the curb and reflect. This office is where I got my start in professional writing (can you call it professional when you don’t get paid?). I spent many late nights here IMing with the girl I’d eventually marry, relishing the air conditioning and working on web sites (who knew nine years later I’d be doing the same thing). This curb (well, the one across the parking lot, in front of the smoking lady who keeps eyeing me up) is where I sat down after my parents called to tell me they were getting separated.

It seemed poetic that I spotted a dandelion a few feet away from where I sat. That summer I was big on dandelions, seeing flowers in the weeds and all that.

And with that I moved on toward Chicago, eventually seeing the skyline open up before me and racing the train towards the looming Sears Tower (it was neck and neck until I passed the Lincoln and took the lead—at least until the next train stop). While I lived in Chicago for a summer, it was rare that I drove downtown. I worked weekends downtown, but I always took the train.

Most of the rest of my trip was business meetings, hanging out and enjoying Chicago’s public art (but that’s another entry). But I did take a walk down Adams Street and Michigan Avenue, remembering my encounters with Leon. His usual spot in front of Panda Express across from the Art Institute of Chicago was empty, though I really didn’t expect to see him. I don’t know where he is, but I hope he moved on and got help after nine years.

Leon was a homeless man. Having never come face to face with gripping poverty before, the summer of 1999 forced me to decide what to do. I could either ignore all the dirty, tired, hungry faces, or I could do something. I opted to befriend one of them, a handicapped man named Leon. We nearly got thrown out of McDonald’s and one day when I had heatstroke he helped me into an air conditioned store and hailed a taxi for me. One day he looked up at the Art Institute and said he wished they’d open it up at night and let the homeless people sleep there.

Walking the streets of Chicago again I saw many faces like Leon’s. Sadly, I didn’t take the time to befriend them. But the usual contradictions and contrasts still bothered me. On one corner I saw a man sitting on the sidewalk and leaning against the building, calling out to passersby to help him out. Across the street I passed a man in a suit telling people they were going to hell. I wondered why he didn’t cross the street and help out the one guy asking for help, but I didn’t help him either.

Just before I left I found myself walking down the street with half a leftover pizza in my hands, and it became much harder to ignore those hungry faces and tell them I couldn’t help. So when one grizzled face asked for help, I held out the pizza box and asked if he were hungry. He shook his head and said something about being too stuffed with that pizza. Apparently he wasn’t that hungry (which proves that a handout isn’t always what they need). Later on I was able to give it to another man who shuffled down the street in long pants and a sweatshirt, carrying a cardboard sign asking for help. His expression never changed, but he took the box and nodded a few times.

I didn’t get to the corner of Michigan Avenue where I earned change swinging my yo-yo. That will have to be another trip. I hit the Art Institute gift shop for the required presents for the family and headed home. I stopped once in DeForest to get gas and make sure I really had seen a giant pink elephant with glasses.

Thus ended my pilgrimage.