Written on August 22, 2026
Share this article with curious people.
This summer, I spent 99 days sleeping on the sidewalks of downtown Chicago.
I’ll write more about this in my book, but for now, here’s an article about my experience.
Why would anyone voluntarily do this?
A few reasons.
First, I have always loved the minimalism and complete trust in Divine Providence that Jesus had. He walked through the desert without food or water. When he got to a well, his friends went to go buy food, and he asked a woman for a drink of water.
Second, Jesus was homeless. He slept in the garden of Gethsemane, on Mount Olivet. This is mentioned in only three verses, spread far apart (Luke 21:37, John 8:1). And Jesus hints at it (Matthew 8:20, Luke 9:58). Am I better than Jesus? Yet he was the cleanest and best dressed man in the whole area. The entire Bible, from Adam and Eve until Revelation, makes it clear that nothing on earth is our true home, that we are only passing through this place until we complete our trial. Heaven is our true home.
Third, I was inspired by two movies years ago. One was Ignatius of Loyola (2016) in which the saint became a homeless pilgrim. The other was Our God’s Brother (1997) written by Pope John Paul II. I wrote two articles (thoughts, survey) about it already. In the movie’s third act, the saint joins the homeless in order to help the homeless.
Pope Benedict XVI made the point somewhere that it’s not material help that can truly help people in poverty, it’s the love transferred to the person in poverty when material help is given to them personally and from genuine love. He argues that systemic support is therefore ineffective and inferior in comparison to individuals giving individually to the needy out of love. Sure, this can be organized and scaled, as St. Mother Theresa and St. Vincent de Paul did, but that’s not the same as it becoming cold and systemic.
There is a fundamental Catholic belief that any suffering you endure patiently for God, you can use as currency to purchase sinners, in other words, to pay the debt they owe God, and obtain for them the grace to quit sin and love truth. St. Monica prayed and sacrificied for years for the grace of conversion for the great St. Augustine, which paid off in spades. Saints used to fast and pray all night for the conversion of this or that individual. St. Louis de Montfort recommends giving all your sufferings to the Blessed Virgin Mary and simply letting her choose how to spend it. This is what I did. Being homeless for 99 days is just another form of suffering.
How did I survive?
First, I was able to easily make money every weekend, by holding a sign that said “Terrible Advice Only $3”, partly to innovate a way that homeless people could earn money, and partly because I did not think begging would be dignified.
Some homeless people I met told me they were making $50 a day on weekdays and $100 on weekends, at least. I tried suggesting they do what I do to earn money, but even if they were making less than me, they said no.
Getting a cheap gym membership allowed me to shower every day. Thrift stores are cheap enough that I could buy new clothes each week. And my briefcase allowed me to store extra socks and underwear, while I was able to wash the old ones in the gym shower with travel Tide. A laptop briefcase is able to store quite a lot more than a laptop.
I moved in the end of winter, beginning of spring, when it was still cold enough that I had to buy a blanket. Fortunately it was only $5 at a thrift store. When that got stolen, another was still only $5.
The hardest part was stashing my briefcase and blanket somewhere safe during the day and night, so they wouldn’t get stolen, and I could travel light. Eventually I found a spot behind a construction wall. Thieves are generally lazy and without imagination, so just the slightest bit of creativity outsmarts them. The only reason my blanket was stolen was because I hung it up on a sidewalk scaffold to dry when it got rained on one day. I didn’t make that mistake again.
For the first month, I slept in a little crevice, between two unrelated construction spots. After that, I slept under awnings when it rained, or just on the open sidewalk right next to the street.
As for food, Jewel has hotdogs, chicken sandwiches, and 10-piece chicken nuggets, for $1 each for lunch and dinner. Extremely good deal, and very filling.
What good things happened to me?
Several times, I would wake up to find food, water, or money next to me.
I met a few friends who, even after I told them I was homeless, still accepted me.
One man, who worked in IT, stopped one morning on the way to work, to have a conversation with me. The whole time, he treated me like a normal person, which was unusual.
One young woman, on the way to work in the morning, asked if she could pray over me. So we held hands and she prayed a sincere prayer for me. She also gave me $20.
More good things happened, but I’ll save that for my book.
What bad things happened to me?
Obviously it was humiliating to sleep outside on the sidewalk. This was very emotionally painful for me.
A few people I knew, when they saw me being homeless, were visibly uncomfortable, and it clearly ruined the relationship. People have the belief that, if you’re homeless, you’re either on drugs or have a mental illness. In general they’re right. That’s basically every other homeless person I saw except me.
Many women (and some men) flirted with me when I was selling Terrible Advice by the bars. I’m listing this in the bad section for two reasons. First, not a single person out there is my type. I’ve never been a bar or nightlife kind of person, which is relatively incompatible with Catholicism. Second, even though I am hoping for true love, I would want it to be romantic but celibate, modeled after the marriage of the Virgin Mary and St. Joseph, who were both celibate virgins their whole lives, even during marriage, yet were deeply in love. This was a choice they each individually made before marriage, having no interest in physical pleasures, only spiritual ones. (Either would have yielded to the other if asked, and happily, given they were the most attractive people alive.) I do not plan on getting married ever again, and the appeal of sex has worn off long ago. I’ve all but lost hope that I’ll ever find such a woman, who wants to fall in love, but without sex or marriage.
One night when I was sleeping, I woke up and found two water bottles next to me. Apparently someone gave them to me, how nice of them. I went back to sleep. I woke up again, because a group of black teenage girls were pouring those water bottles on me.
One night, a very drunk, very large man told me to stop sleeping on the sidewalk, and to go find a spot under a bridge. He was clearly ready to get violent, and he was just “breathing threats and murder”, like Saul on the road to Damascus.
I saw him again a few nights later. He was across the street with his friend, shouting insults at me. So I literally stood up for myself. He then crossed the street. My attempt to deescalate it by introducing myself and trying to shake his hand, was useless. He was too drunk and too angry. He just kept walking into me with his alcohol-sweat drenched shirt pressing up against my clean button-up, and his alcohol-saturated breath distracting me from thinking of what to say or do. Later, his friend came back and apologized to me, and offered me his leftover food, which I declined.
One evening, I finished dinner at Panera on State St. and noticed their bathroom was out of toiler paper. It was slow, and two lazy employees were chatting. I let them know about it and they did nothing. An hour later I let them know again, and as I walked away one told the other I was pissing her off. An hour later, I let them know again, still nothing. Finally, 20 minutes before closing, I asked if they could fix it. They said no, they have none, a truck would be coming. First thing in the morning, 6am sharp, as soon as they opened, I went in and told one of the hard working employees, and he immediately put some in their bathroom. They had it all along. Those two girls should be fired. Better that they’re fired, learn their lesson, and go to heaven, than remain lazy liars, and go to hell forever.
One night, a very fat black woman in what looked like a police uniform, but which I now know to be a security guard uniform, who I believe worked at the SAIC residence on State St., came over when I was praying the Rosary and laying down, and loudly told me to move. She lied and told me it was illegal to be homeless (it’s not). She looked like a police officer so it tricked me into thinking she was. She threatened to spray me with pepper spray if I didn’t move. She didn’t listen to almost anything I said, and just kept shouting “MOVE.” She grabbed my blanket and walked 50 feet south and threw it on the ground. I hope she gets fired, but more importantly, I hope she develops any compassion. Heaven certainly doesn’t let bullies and liars like her in. I’ve been bullied my whole life, and I was disappointed that I gave in again. So the next night, I slept in that same spot, preparing myself to be pepper sprayed for standing up for myself, but she didn’t come over and tell me to move.
Eventually I had to buy Off! bug spray, because waking up to mosquito bites was extremely unpleasant. It mostly worked, but it was expensive.
More bad things happened, but I’ll save that for my book.
The end
Anyway, I moved back to my hometown.
I’m still recovering from the trauma of being bullied and threatened, and losing a few friends and acquaintances and the respect of the general public. So you won’t see me as much, as I’m taking a little time off, to focus entirely on my book.
