My Night On The Street | How Emerging From Homelessness Is Harder Than You Think

In February this year my best friend Brian was doing research to write a grad school paper. He’s studying Marriage and Family Therapy. He was required to interact with, and write a paper on, interacting with a disadvantaged minority group. Brian chose to spend a night on the street as a homeless person. When he told me the idea I thought it sounded pretty awesome. I mean, haven’t you always dreamt of sleeping exposed on the street? Well, for me, I actually had wanted to spend a night on the street for a while.

Doing Our Homeless Homework

Leading up to our night on the street we did our homework. We visited a place called the Isaiah Project (aka The Waterman), who gives out water in downtown San Diego to the homeless. These dudes were pretty rugged. A number of the people who worked for this non-profit were actually still spending their nights on the street. Like it wasn’t even a big deal. Saving money, showering in the morning, eating fast food, doing their thing.

They were pretty cool people, but warned us that it was going to be dangerous. We wanted to be safe, but one of our new friends, apparently an aspiring boxer because he spent half the time talking to us while hitting a heavy bag. (I also think he wanted to be intimidating to any potential water thugs). He shushed the guy that was gonna give us safety tips. He said, “No way man, they aren’t going to get the homeless experience without the feeling of danger. They’ve got to be in danger.”

They reminded us that sometimes kids get stuck on the street. They don’t know where to go or where it’s safest. They don’t know how to get food. They don’t have tazers and pepper spray to protect them. They’ve got to figure it out on our own.

Danger Danger

I actually wasn’t too worried about “danger” yet, I just wanted to know where to go to the bathroom during the night or in the middle of the day. I didn’t really get any tips, other than to pee on a building or hopefully not get kicked out of Burger King or the Public Library because I look like someone who spent the night on the street.

night on the street

Not everyone lives like this on the street.

We made our way to the Salvation Army and bought some sleeping bags and old clothes to do our best to not look like middle-class white folk faking it on the streets.

Finally later that night we headed back downtown around 10PM and found the area most populated by homeless people. We figured under the street lights sleeping near where other’s thought was safest was the best place to spend a night on the street. I could see how someone might think hidden away from everyone is a good spot, but that’s probably where people get robbed and taken advantage of.

Getting Our Fragrance On

Sleeping like a homeless person wasn’t that difficult. Our adrenaline was pumping as we imagined the worst-crazed hoodlums stabbing newcomers with makeshift knifes while pulling crack out of their butts. AND we thought we definitely looked like  and smelt like newcomers. So Brian and I didn’t shave for days and even smoked a couple cigarettes (my first ever actually, how do people inhale that hot fiery stuff?) because we were convinced people would smell our phoniness. I even rubbed my clothes against my tires because Brian thought I looked too clean.

night on the street

I was surprised to see how organized many people sleeping on the street are.

Once we had laid down under the bright street lights a few feet away from other homeless on our left and right, we slipped into our sleeping bags and settled down. We chilled and talked for a bit, and tried to take it easy.

Where we were sleeping wasn’t far from the bars and clubs so it was really odd to have nice shoes and pants walking past my face around midnight shouting drunken profanities. It was really strange actually. Kind of like I was this invisible person-someone who didn’t exist. My friend is a grad school student, has a wife and child. Lives in a nice house. I wonder how different we were from the rest of the people sleeping on the street. Just one bad situation, bad illness, or bad choice away from having to spend the night on the street for real.

It was kind of hard to fall asleep. People’s feet scurrying just a few feet from my face had me frequently waking up throughout the night afraid I’d get stabbed in my sleep.

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  1. This is a very interesting concept to me. Living downtown in a major city since college, I’m exposed to several homeless people per day. I often wonder how they became homeless and why they don’t take the steps to get a simple part-time job. I’ve come to the conclusion (maybe incorrectly) that many homeless have mental issues or drug problems. Did you experience this at all John?

    • JW, thanks for crediting me with this aritcle. 🙂 I’m guessing you meant to ask Todd that last question. But since it’s a Monday morning at work I think I’ll go ahead and answer. I have the same conclusion as you because I believe you don’t become homeless overnight but it’s through a series of bad decisions over months or years. At the same time I sympathize with them because we all do our best with the cards we’re handed. I’m fortunate to have had a somewhat stable childhood, while some grow up in foster homes or on the streets. I’m sure a percentage have “baggage” because of horrific experiences while kids like abuse or lack of direction and education. For some their lives seem to be decided before they even hit 18. So I guess I try not to generalize or stereotype them, even though my brain says otherwise, because in the end they do need help. I won’t offer money but try to help in other ways. I’ve found food to be the best option along with some encouraging Godly words.

    • Todd Mayfield says

      It’s true that there are a number of homeless with mental problems. It’s a sad state because some of those people have families that want to help, but they just “disappeared.” Some are mentally off enough that they may prefer living on the street.

      Drug abuse is a problem, it may have led some people to the street from repeated bad mistakes. But I don’t think it’s what’s keeping people there. Several drug users had plans and goals to get off the street, it really is extremely hard to get rolling.

      When you are spending two hours walking to a place that serves breakfast, then walking an hour to panhandle, then walking another two hours to get dinner, it’s hard to have the time to apply for jobs. When you’re walking around with all you own under your own, you’re not allowed into the library to surf the net and look for jobs. Even if you landed an interview, the amount of effort it would take to wash your clothes, get a shower, then walk however many miles/hours to the interview is challenging.

      They are programs out there to help people, but they are often full, and awareness is low.

  2. I think that real homeless people figure out places they can go to pee and get water. I’m not saying it’s easy and I’m not saying they don’t get kicked out of most places, but I think if you’re on the street for awhile, you start to know where you can go to get what you need… or at least you know of a handful of places and hopefuly one pans out on any given day. It’s crazy you did this, dude, and pretty aweomse actually. What an experience. I wouldn’t have slept well either. And then to have nicely dressed people walking around so close to you… weird. And sucky.

    • Todd Mayfield says

      People definitely figure out their routine. Some people just pee in public. But people that don’t want to stoop that low sometimes walk an hour (maybe a couple miles) to pee under a bridge or something.

      If there’s any luxury in life that I missed being around poor people, it was having a toilet!

  3. Todd,

    I really enjoyed this article.

    I wonder, were you able to engage people in conversation, or were you seen as outsiders because you were “new” guys on the street?

    • Todd Mayfield says

      Great question. No one thought we were outsiders. Some people on the street really didn’t even look that “homeless.” They hadn’t been beat down by years in the son yet. I think we just looked like people down on our luck. But sure, other homeless were very warm and inviting. These people want to help each other.

  4. Love this. I’ve been challenging myself to take more responsibility for my homeless neighbors in Los Angeles. I’m convinced most of them got there because of a deficiency of love. In their lives they weren’t loved and honored enough, and this lack of value became their reality. Honor is simply showing someone their value, and I’ve been trying to think of creative ways to do that with what is in my hand. Sometimes that is money, but sometimes I don’t have money to give, so I think of other ways to show them their value. One of the biggest ones you mentioned in this post: simply acknowledging them- making eye contact – smiling- saying hi! I imagine most of them got there because they were simply overlooked their whole lives! The second thing I’m trying out is simply using the gifts or talents God has given me to bless them. Things that I hope one day to be paid for doing, I offer freely to them to show them value and bring hope and beauty into their lives. It’s not easy. Often the conversations are awkward and frequently end in a proposal of marriage, but when I take the time I always walk away knowing more about the heart of Jesus…and that is worth pushing past any discomfort or fear.

    • Todd Mayfield says

      Wow that’s really good Jewel! It’s true, I think people on the street certainly are down because they are “poor.” But what’s even more disheartening and paralyzing? Being poor in spirit.

      There’s a small proportion of homeless that like to live that life. I assume they live by the beach or rivers (totally making that up).

      If I were living on the street, and wasn’t in touch with family that could help, I don’t know how I’d get off it. It seems too hard to eat, drink, sleep, and bathe to track down a job and get hired.

      I did meet one homeless guy that had a job. He didn’t get paid much, but he was planning on staying on the street for another 6-12 months until he saved enough money to stay someplace for a while. I assume he would then attempt to get a better job.

  5. Great post/experiment Todd. Here in Vancouver most of the homeless have to sleep during the day for safety reasons. Then when it’s dark out they are awake so they are not as easy a target. That would sure contribute to the difficulty in finding work to get out of their situation. As much as I’d like to give money directly to them, the sad truth is most would be using that money for alcohol or drugs. So food or clothing is a much better option.

    • Todd Mayfield says

      It’s true that some will use the money for alcohol or drugs, but possibly less than you might think. The problem is, there’s no way to tell who will and who won’t unless you know them.

      We actually have a pretty big homeless community in San Diego, and there’s a lot of homeless kids born into it, or brought into it with their parents. Down here there’s some cool opportunities to help kids out in these situations like Monarch Schools ( I actually found out about them at a fundraiser at a dive bar!

  6. This was a very interesting read. Homelessness is kind of a foreign concept to me being from a tiny town away from the big city. It’s always a shock to see it when traveling through a larger city. I’d never thought about the struggles with basic things like a place to relieve yourself or finding clean water to drink.

  7. This is a great article Todd. I’m not real sure why you did it though? As a child I ran away from my foster home and spend about a year on the street. Our worst fear was the cops! As an adult when i got into trouble, lost my job, got kicked out the house or what ever, The street was a natural place to return. My last stretch of homelessness lasted about half of 2007, and it was God and God alone that got me off the street! And is now disciplining me to stay off the streets, be a good husband and father. Our homeless need Love and prayer! We have to learn how to Love the homeless like they were our own kids. (Better yet, James 1:27 says: Religion that God our father accepts as pure and faultless is this: to look after orphans and widows in the distress and to keep oneself from being polluted by the world.) Maybe your next experiment should be to bring one of these widows and orphans home with you, give them a good meal, let them take a shower with some hot water and tell them that Jesus Love’s them! Don’t forget to tell them that he will free them, if they are willing to submit! I mean brake all the chains of bondage.

    • Todd Mayfield says

      Wow that’s a wild story. What did it take to get back off the street? Was it going to friends and family, or were there other steps you took? Thanks for the insight and encouragement!

  8. Homeless people have suffered great rejection and abandonment in their lives. My heart cries out for grace and justice for them all at the same time. I’ve recently been seeking the Lord about how He would have me help some of the homeless people in my city in China. I’ve had a friend teach me how to say “God loves you. I love you.” in Chinese and want to say this when I offer help of any kind. (I’d leave out the “I love you.” part if it’s a guy.) But my heart longs to do so much more. Once I know more Chinese I’ve thought about taking them to get a new shirt or coat or other clothing they need too or take blankets and give them out when it’s cold.

    I’ve noticed a couple aspects not mentioned regarding homeless people getting a job to help themselves get off the streets. You have to fill out an application to get a job and you’re required to put your address and phone number so they can contact you later for an interview. When you have no address or phone the likelihood of getting an interview is next to nothing unless they interview you & hire you on the spot. But, then they still want your phone number to contact you if you aren’t at work when your supposed to be, etc. Then, there’s the aspect of showing your new employer your actual Social Security card and picture ID to fill out required government forms. I’m sure all the obstacles before them are daunting when you’re homeless; and, how hopeless that must make them feel.

    To have experienced a night on the streets must have been very eye opening in many ways. The next step is what one should do with this knowledge (beyond sharing the experience with others or writing a grad paper). May EACH of us be sensitive to the Spirit in how He would have us walk out Matthew 25:34-40 so that those in need on the streets will experience the love of Christ and be drawn closer to Him.

    • Todd Mayfield says

      Your points in your 2nd paragraph are really true. There are just so many obstacles to go through for homeless people. Many people say it’s not impossible, and it may not be. But it’s so confusing and difficult that while you’re down on your luck and in despair, man it’s got to be tough to do all the little and big things to emerge from homelessness.

      As for the homeless in China, do you think they’re there for the same reasons American homeless are? What does China do to help them? Very interested to know the difference.

  9. Interesting article, thanks for sharing. I have a few friends who did the homeless experience thing, as part of a program called YWAM, in Vancouver. A lot of them had mixed feelings about it. This was a different take. I appreciate that you took the time to write it 🙂

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