My Afternoon as a Homeless Man

Post 22 - Sign

For a brief period three years ago, almost to the day, I was homeless. (By brief, I mean “two hours.”)  Voluntarily.

This post is about what I learned – and who I met – when I decided to dress “homeless” and stand on a street corner in Baltimore panhandling for change.

The Backstory:
Coming out of grad school, I struggled to find a company/position that was a good match. And, in my first three years out, I went through just as many employers. When I finally signed with my current job (where I’ve been since December 2016), I was thankful for the opportunity. While my finances during that period of job-hopping were somewhat…shaky, I was always thankful that I never had to beg on the street for money.  So after a period of what I hope was as close to it as I would come, I wanted to see what homelessness was like first-hand.

I put on the oldest, rattiest clothes I had, went outside to roll in the mud, and rubbed some dirt on my face.

I wrote up my cardboard sign (pictured at the top), sprayed it with cooking spray to make it look worn, and headed to an intersection where I’ve seen lots of homeless men and women panhandling before.

My plan was to stand outside for two hours and see what would happen. I took my ID and $10 in small bills.

Everything I could gather, I promised myself, I would give to whichever other homeless people were around at the end of my “shift.”

As soon as I got to the corner and stood on the median, I immediately felt a sense of shame. It was instantaneous. Like, this is finally what my life had come to. Obviously, I didn’t have to be there, but the shock that I was now one of the people standing in an intersection, holding a cardboard sign, asking for spare change, stuck with me longer than I was expecting.

At first, a few cars ignored me, and I figured that they somehow knew I wasn’t homeless. But after a few minutes, I got my first donation.

It was from a young Hispanic man, probably in his thirties, driving maybe a 10 year old Toyota or Honda. He handed me two quarters.  (Remember the story of the Widow’s Mite?

Two copper coins was all she had to put into the temple offertory, and Jesus pointed out that she was the one who gave the most: she gave out of her poverty, while the others gave out of their abundance. Mark 12:41-44) I wasn’t all that surprised to see a small change donation, but I remember being so humbled and honored that I was just standing there looking helpless, and this man reached into his pocket and gave money that he had worked for just to help me. No questions, no contingencies, no request or expectation of repayment. Just generosity. As if to say, “you look like you’re in need, and I can help. Here you go.” It was one of the most profoundly touching experiences that I’ve had. And that alone almost made my eyes water. Those two coins are the only ones I kept from that day, and I still have them.

I kept some mental stats on the day, and minorities dramatically over-represented in giving. About one out of every two or three minorities gave something, whereas about one out of every ten white people gave something.

A few more cars passed by, and eventually someone else rolled down their window for me.  Another young man. Maybe in his early twenties, with a few other people in his car. I think it was a Honda Civic, the kind with a poor tint job on the windows, mismatched fenders and door panels, and a coffee-can-weed-whacker-sounding muffler. The man seemed to match the car.  He had a few piercings, the obligatory dyed hair, tattoos, and dark clothing.

The guy handed me an overflowing handful of change. It looked like he emptied out his change tray. In fact, he needed two hands to pass it all to me. And he was so nice about it, too.  That stuck out the most. He smiled genuinely and said, “Hey!  Here you go man.  Good luck. Hang in there.” But it came across so relatable as if he were saying, “hey, I get it. I’ve been on the outside too.” (In my experience, people who dress counter-culture are usually some of the nicest, most accepting people around. They know what it’s like to be unfairly judged or mistreated.)

Luxury cars, brand new cars, or cars with any kind of religious decorations didn’t give anything. At all.

I wasn’t surprised by the luxury cars, and I was only a little surprised by the new cars, but the religious emblems surprised me a lot. You can draw your own conclusions about hanging something from your mirror verses holding something in your heart, but as a Christian, I was shocked and embarrassed to see that so few people who wore the badge wouldn’t put their faith into action in that circumstance. After a while, I wanted to just point to whatever icon was hanging from their rearview mirror as they sat awkwardly in their cars next to me.  Maybe I should have given them a few bucks…

A little while later, a cop car rolled up.  As he approached my intersection, he turned on his lights, and when he pulled into the turning lane (right near the median where I was standing), I figured he was coming for me.  My plan was to play the character as long as I could without lying, and really experience what it was like for a homeless man to get hassled by the cops.  But instead, he just looked at me, smiled kindly, and pulled a U-turn to go back the other way.

Another memorable gift was from a man driving an Isuzu box truck. He was probably in his forties, handsome, and well-dressed for a guy driving a delivery truck. (Not like suit-and-tie, but new-ish, quality, work-appropriate clothes.) He didn’t look flashy by any means, but he looked like he had his life together: he was driving the truck, and he was 100% content with that. Rather than money, he handed me two oranges. Now, I’ve talked to some people who don’t want to give money to the homeless out of fear of enabling a drug habit, so they give food instead. This man was the only one who did that, and it was pretty touching on a different level.

If he was anything like me or my wife, he knew exactly what he wanted to eat that morning when he packed his lunch. And he was probably looking forward to working through every stage of food that he brought. Somewhere in there, his oranges were part of that plan. But this day, he saw me, saw that I was in need, and shared what he had. And it wasn’t like he was bringing a pre-meditated gift to a party, or inviting a houseguest to look through his refrigerator or pantry and take from his abundance.  No, he actually gave a portion of his entire lunch to someone who he thought needed it. Just opened up his lunchbox and shared what he had.  Somehow, I have a feeling this man’s heart was accustomed to operating the same way.

Then there was another man, also in a truck, that stuck out, too. He was noticeably different from the man in the delivery truck. Maybe 10 years older, but he wore his age like it had been a heavy burden. Like he had lived a rough life and his face was a testament to it. He drove an old pickup truck. When he stopped at the intersection a few cars away from me, his window was down, and I heard him mumble something. As I got closer I asked him what he said and he didn’t answer. I asked him again as humbly as possible, and he said with a thick rural accent, “I can’t do nothin’ for ya.”

And very quickly, a lot of thoughts ran through my head. First, I was somewhat pleased that my disguise was good enough to convince him that I was homeless. Second, part of me wanted to challenge him on the word “can’t.” I thought about engaging him and asking, “can’t, or won’t?” And then, however he responded, I was planning to use big words and complex sentence structure to upset his perception of the level of intelligence a homeless person might have. But then, finally, I thought better of it. If I were to do that, I’m sure he would have drove away completely turned off from homeless people. More so than he already was. I wasn’t going to win him over by making him feel guilty (or stupid), and I didn’t want to push him away any further for the next homeless person who may have been in serious need. So, I just smiled and said reassuringly, “that’s okay.”

As I thought about our exchange, it felt a little surreal. Yes, I was standing on the street holding a sign, but in reality, this man had no idea about that which he seemed so certain. I had more teeth then he did, straighter and whiter. I drove a better car. I spoke with better grammar, which implies more education. And, I am willing to bet, that this new job of mine paid more than his job. And he was looking down on me, withholding his benevolent help and mercy.  (<-sarcasm)

The longer I thought about it, I began to wonder if my view of this interaction was at all similar to how God sees some of our actions or reactions in certain cases. We only see the surface of people, of situations, of problems, of challenges, of anything. Our scope is so limited by time and the world that we know around us. We have, like this man in the pickup truck, no idea what really is, or what’s really going on behind the scenes. Yet, like the man, oh, we are absolutely certain about what’s happening, and what we can do. Or can’t do.

That exchange didn’t hurt my pride.  Maybe because at my core, I knew that I was somehow better than that man.  Or that I was really just playing a character and not engaging with him genuinely.  I don’t know.  Maybe my pride was/is so powerful a monster that the piddly arrows he slung at me didn’t even stick to the scales.  I hope that’s not the case, but if so, I have some work to do.

As I write this now, three years wiser, I wonder if this man actually touched my heart more than any of the others. Not by what he did for me, but by revealing to me me what I was…

So my time was up, and I had collected about $20, which was a solid haul for someone with zero bills and almost no expenses.  True to my plan, I began looking for the nearest homeless person to unload my bounty on. The two men that were in the same intersection earlier in the day had moved on. And as I looked around, the only person I saw was a young woman sitting on the curb of a carwash nearby. She had been there about a half hour. She was wearing older clothes, but she didn’t look too destitute. What gave her away was that she was sitting on the curb near a carwash at 2:00 pm on a weekday. Most people at carwashes are either walking into the store or out of the store. Not sitting there.

I walked over to her. As I got closer, the first thing I noticed was how pretty she was. I’m willing to bet that in high school, she was the dream girl for more than a few young men. And with a shower, makeup, and decent clothes, I don’t think she’d ever have to buy her own drink in a bar.

The sad part is that I don’t think being “pretty” is the asset for homeless women that it is for women in offices.


Me, smiling: “Hi, are you looking for money?”
She, perking up: “Yeah!”

I reached into my pockets and started giving her the haul from the day. She was surprised and said, “no no. This is yours. You’ve been working for it. You earned it.”

Me: “No no, really. It’s okay. I got more than I need for the day. Why don’t you take the rest. Do you like oranges? Someone gave them to me, and I’m not crazy about them. Here.”
She, smiling: “Oh, thank you!  What’s your name?”
Me: “Cory. What’s yours?”
She: “Lindsay / Sarah / Jennifer…”

To this day, I wish I could remember. When she told me her name, it was something very normal, like Lindsay or Sarah or Jennifer. I don’t know why, but I was expecting a homeless woman to have a strange and unusual name.  Really, no name at all. Maybe because on some level, I didn’t believe (or didn’t want to believe) that homeless people were actually people, but a subgroup all their own.

As she took the money, she hesitated, “are you sure?”
Me: “Of course. It’s much harder out here for women than for men.”
Jennifer: “I know! I keep telling my boyfriend that, but he’s like, ‘just stand out on the street and people will give you money.’ But I’m like, ‘no, they all want sex, and I don’t want to do that.’”
Me: “Ugh, that’s terrible. Do you have a place to stay warm?”
Jennifer: “Yeah, my boyfriend and I have a tent behind Wendy’s. What about you? Do you need a place? You could stay with us.”

This woman that I met 90 seconds ago was ready to open up her home to me. I had given her about an hour’s wages, and a small amount of genuine kindness, and she was ready to open her home. She offered to let me sleep next to her (literally, not sexually) for my own warmth, safety, shelter. All she had, she was ready to share it.

It really made me think about my own situation. If I had met a man on the street and he needed help, I don’t think I could invite him into my home to stay, let alone my bed. If the I-can’t-do-nothin’-for-ya man was one end of the spectrum, Jennifer was the other. And if he was showing me what I was, she was showing me what I should be.

It reminded me of Abraham’s nephew, Lot, in the town of Sodom. When the angels went to stay with him, the men of the town wanted to gangrape his guests. Instead, Lot offered his two daughters in their place as a substitute. Here’s the story. (Genesis 19:1-29)

Me: “I’m okay. I have a place to stay a little bit north of here. Do you need anything else?”
Jennifer: “No. Thank you. This was wonderful.” And she gave me a hug.  A really good hug.
Me: “Okay. Maybe I’ll see you around.”
Jennifer: “Okay. Bye, Cory.”
Me: “Bye, Jennifer.”

I walked away. Across the street, and around the corner. Into the parking lot at the nearby strip mall. I got in my car, turned on the heat, and went back to my house to shower. And eat lunch.

One thought on “My Afternoon as a Homeless Man

  1. From a mothers point of view: Im glad I didn’t know when you were out there…my heart would’ve been hanging on that corner with you. Your in depth search for the truth at all levels comes to the very forefront with this message. None of us know where the other comes from, what they’ve been through, where they are going. We can only assume compassion for them & an uninformed but “no requirements necessary” love for them.
    As you learned “They” all come in different colors & sizes…many among us in very well chosen costumes…suits, uniforms, gowns, jeans. The person on the corner we obviously see he is in need of help….the person in the car driving by…??? We all are in need of something but struggle to identify what it is. Feeling lost or inadequate would likely define the majority of us. The joke is helping the person next to you who is empty can fill your own personal void. Quarters, dimes, oranges, time…the message is give what you can to help. Prayer is the most powerful & fulfilling…..& to remind them all they’re not alone because there’s a big guy in the sky with arms outstretched waiting to give them a hug like you did for that girl sitting on the curb.
    I am continually learning myself, thank you for the reminders. Your “first day I met you soul” still warms my heart, makes me proud, & makes me so appreciative that you are who you are….lucky world.


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