What 36 Hours on the Streets of Chicago Taught Me

Gene had picked me up from O’Hare, and we were sitting at a small café in Chicago’s Pilsen neighborhood. It was winter — snowy and much colder than the Oregon I’d left behind.

“So… why are you here?” he asked.

I grew up in suburbia and had recently come across the writings of Dorothy Day, co-founder of the Catholic Worker movement, where she spoke about not only loving the poor, but living with them. Her words and experience seemed very foreign, but struck home with me — it rang true. She had fleshed out her faith into a radical way of life. It was a way of being a Christian that I’d been longing for, aching for, and I just had to find out if it was possible — if other people were doing it as Dorothy described it, if I could do it.

But where to start? A friend had contacts with the Urban Life Center in Chicago, and they were hosting an “urban plunge” — an experience that invites people to spend 36 hours on the streets to see the world through the eyes of people living in poverty in the city. Stepping into poverty on the plunge would give me a new perspective on my faith and the opportunity to make a visit to the Catholic Worker house on Chicago’s north side to actually meet people who were living like Dorothy Day was.

So I packed a box of books and a bag of clothes, and went. Gene ran the Urban Life Center and was the first person I met when I arrived. He agreed to let me stay at the center and teach me how to make it in the city. Other than that, Gene knew nothing about me. Hence his question.

My reply didn’t really clear things up. “I’m here to die,” I flatly stated. It was very dramatic, but I was searching for a new way to live. Gene’s eyebrow twitched.

I proceeded to blurt out my story, and Gene just sat there and took it in. As a veteran peacemaker, activist, and educator, Gene knew all about youthful idealism, and I was grateful that he didn’t scoff at mine. “Well, I don’t know about dying,” he eventually said, “but you’ll find plenty of poverty here.”

Once I got settled in the Urban Life Center residence, I went with the other students to a thrift store to purchase warm, non-designer attire. We were told that we’d be dropped off in the middle of the Loop the next morning and urged not to return until the following evening. Each of us would be provided with a subway token and a dollar.

It was snowing (of course) when we were dispersed downtown around sunrise. I wandered for a while, taking in the skyscrapers and morning bustle, and then decided to augment my dollar with a bit of panhandling outside a McDonald’s. I was genuinely grateful for the generosity I encountered, and I made more than enough for a burger and fries. I went inside to eat and get warm.

Next came more wandering, and then I made a stab at the Art Institute. “How much to get in?” I winced.

The lady behind the counter gave me a once-over before replying. “There’s no actual fee. Only a suggested donation.”

“A donation? Uh, how about a dime?” She sighed and shrugged and gave me a ticket, and I spent the rest of the afternoon mingling with masterpieces.

After the Art Institute closed, I made my way to a homeless mission center for supper and sleep. By then, I was starting to feel sick — achy and feverish — and I could not keep my eyes open during the church service before dinner (a casserole of some kind, as I recall, and maybe some vegetables). Along with scores of other men, I showered and then found a cot in an enormous, overwarm room. The snoring was deafening. I chatted with the night clerk for a while, but soon I nodded off.

The next day, bright and early, we were all up and fed — freeze-dried eggs, black coffee — and back out on the streets. I used the rest of my cash to take the “L” up to the north side to track down the Catholic Worker house. All I had was an address on Kenmore Avenue, and when I finally found it, I stood across the street and stared. I was way too intimidated to go in — too overwhelmed by the proximity of the end of my quest. I recall someone inside peeking out around a curtain for a bit. I was standing in snow. It was freezing — I was freezing. I reluctantly moved on to seek alternative shelter.

I stopped in at a public library to thaw, but I fell asleep and was asked to leave. My aches and fever were getting nasty at that point, plus I was disgusted with myself for copping out on the Worker. I dug out my subway token and headed home early.

As the train rattled its way southward, I coughed and snoozed, and in between I mulled over my plunge experience. “Those other guys will be back in the mission tonight,” I thought, “but I have a place to go home to” — not to mention resources and a college education and options.

My foray into the world of homeless poverty was an epiphany, but it seemed phony and hollow. I didn’t even last the whole 36 hours. And I chickened out from entering the Catholic Worker house and learning more about their way of life.

But it was a start. Over time, I’d return to the Catholic Worker and actually summon the courage to serve and share life there. There were more lessons ahead of me, inspired by Day’s vision see Christ in “even the lowest, most depraved” and “love them to folly.”

The monk and writer Thomas Merton wrote, “The only true joy on earth is to escape from the prison of our own self-hood.” When I left Oregon for Chicago that winter, I didn’t make the whole journey I set out on — I didn’t find and commit to the faith I sought all at once — but I had taken a step, which could lead to others.