The System

By Colleen Edwards


Go outside and sleep on the streets. Sleep on the side of a dumpster. Sleep, but only where nobody can see you. Sleep, but with a knife because someone will rob you. Sleep, but with your children tied around your waist because someone will try and take them. Sleep, but only after having not eaten all day—hunger pains will keep you awake.

Welcome to the houseless experience. 

I have been volunteering and working within the homeless system for the past six years. I’ve volunteered in shelters and on buses, I worked with homeless youth for a year and then switched to working directly with case managers, clients, and landlords. I studied journalism in college and spent two years reporting on people on the streets of San Diego. 

I want to begin by saying I am nowhere near an expert on the homeless system.

The system is broad and incorporates different practices and strategies for each specific houseless subpopulation. Here are some experts in the houseless world that are worth a follow if you are interested: Ann Marie Oliva, Peggy Peattie, and Corianne Payton Scally.

I recently left my job working with Chicago’s homeless, and learned a lot in the past couple of years working directly in the system. 

During the first year, it was my job to form a Youth Action Board. A Youth Action Board (YAB) is a critical part of Continuum of Care (CoC) funding for agencies to get the money they need to house people. It was December of 2020, middle of COVID, and I was assigned to go out and find homeless youth aged 18-24 to participate in the YAB. The YAB’s core function is to receive lived experience expertise from the youths who actually live on the streets. Remember, most kids are on the streets because they’ve been made to believe living on the streets is safer than any other option they have. 

A lot of homeless youth were placed in hotels and motels during COVID, so I went out to see if any of them wanted to join the board. These motels were often in dangerous areas, and there were people and groups you knew to avoid. I’ll never forget the first two men I met who agreed to join. I carried around $25 gift cards from my organization to get them to speak with me for ten minutes about joining. One was 16 and the other was 18. They didn’t really have any family and both were working on figuring out a way to get to Oregon. I met with them about four times. 

The streets of Chicago in winter.

They were funny, sweet, and always willing to share their experiences. They had been on the streets for a year. They grew tiny tomato plants in the window of their motel room. 

Every time I came with the gift cards, they would be happy, because it meant they would be able to eat that day. On one occasion, I brought donuts because one of them had a birthday coming up. 

He looked confused and sad and happy at the same time. He whispered, “This is the first birthday gift I have ever received.”

Anyone who claims that homeless youth need to “grow up and get home” is an asshole. 

One little girl, who was probably about 11 years old, met me in the parking lot of her motel for a gift card. It was probably 10 degrees with massive wind chills. (Chicago winters are no joke and the amount of homeless people that die on the streets is heartbreaking.)

She came out with no shoes and a flimsy little sweatshirt. She didn’t say a word. She was scared of the men standing around the parking lot. She took the gift card, looked up at me once, and left. Her face will forever be etched in my mind—she looked like she had the entire weight of the world on her and didn’t know what to do with it.

No hope, no wonder, no thoughts of ever believing anything could be different. 

I regret not going to buy her shoes every single day. I think about her often. 

A year later, I switched jobs and became a housing associate in Chicago. It was here that I really learned about the ins and the outs of the homeless services system. 

I worked with a team of five women who were all around my age. It is difficult to explain the type of bond we had. When you work within the social services field, there is a different kind of understanding between coworkers. Every day, we felt the weight of human life in our hands. We heard our clients’ stories, we vouched for them, we struggled when landlords couldn’t see past what was on paper. My little group of coworkers will remain the most inspiring group of women I know. I was lucky to work alongside them.

We worked with different homeless service agencies, shelters, case managers, landlords, and property managers throughout the city of Chicago. The types of discrimination I saw were horrendous. 

The one question I consistently get asked is “Why are the majority of people homeless?”

It’s not because they’re lazy. It’s not because they’re criminals. It’s not because they want to be on the streets. 

I have spoken to hundreds of people on the streets throughout my life, and here are a few of the main reasons people are homeless: 

  1. They had a rough childhood (parents weren’t around, they were abused, had no support ever, etc) and aged out of foster care with no skills and nowhere to go.

  2. They have paying jobs (this is the case for many homeless), but just don’t make enough money to afford rent or support themselves. 

  3. They are victims of domestic violence. The amount of women and children who are fleeing domestic violence is appalling. 

  4. They were evicted because they couldn’t pay rent (often they have serious health issues and their medical bills are exorbitant). If you’re evicted at any point in your life, it is close to impossible to try to get a new landlord to rent to you, no matter how far you’ve come since the eviction. 

  5. Homeless youths are typically running away from dangerous home lives, kicked out of their homes, or don’t have a home to go back to in the first place. 

Homeless in San Diego, California.

One day, I went on a ride along with a couple of case managers. They are assigned to check on clients on the streets. They usually know exactly where people are hiding. We went behind an abandoned house into the woods.

Here, an older man had been living in the forest for 25 years. He had piles of things. Old children's toys, tremendous amounts of trash, tarps, and junk lying everywhere. He had an oxygen tank and was close to 90 years old. He was a math teacher his entire life at the local high school, but after his wife died, he couldn’t stand the thought of living in his house anymore. He left his house and retreated to the forest, where he has stayed ever since. Every time the case managers tried to get him into a shelter, he refused.

Grief, especially when you have nobody to lean on, can be all-consuming. Sometimes people just want to be left alone, and that’s okay. 

The landlords were a different kind of abhorrent. Some of them were helpful and really did want to get people off the streets. However, most didn’t care at all, were just in it for the money, and didn’t give two shits about where they placed people or what condition their apartments were in. 

It usually takes a bit of time to get people through the application process and into apartments. We hosted AMEs (Accelerated Moving Events) where people who had received housing vouchers would come in and pick which apartment they wanted to live in. We had anywhere from 40 to 60 people at each of these events, and after they were over, it was part of my job to send over the application to the landlord of the apartment that was chosen. Some landlords had extremely strict requirements, and some had almost none at all. 

I had a landlord cancel a move the day before a client was supposed to receive his keys because he hadn’t paid his $35 portion on the voucher. His paycheck didn’t come until Monday. It was Friday. The move was canceled. 

We had a landlord ask if clients were “professionally homeless.” What they meant by that was—we don’t want anyone in our buildings that has been on the streets for an extended period, or wasn’t receiving benefits, or didn’t have a job.

I worked with a family who were victims of domestic violence, fleeing a dangerous situation. It was a mom and her four girls and they were moved into an apartment building. Her apartment was broken into and her youngest daughter raped by another tenant in the building. 

After countless complaints about safety, the landlord did nothing. That story still haunts me. 

A homeless individual’s living situation near the Ocean Beach Pier, San Diego, CA.

The system is broken.

Some people wait for years (sometimes decades) before they can receive housing vouchers to get into apartments. They are chosen for vouchers based on who is higher risk, and this can look different in certain situations.

Once they get these vouchers, they still face discrimination from landlords on all fronts.

So, when a client states they want to remain on the streets, it is often a result of how many times the system has failed them. They don’t want to get their hopes up anymore for something that may never happen. 

Many people make the mistake of thinking they know exactly how to help another person. You need to ask what the other person needs instead of making assumptions based on your own biases and judgments. We often have no idea what kind of past trauma people carry, and this holds true for everyone we meet. Be gentle, be kind, and be understanding. 

Honestly, I don’t have a lot of advice to give. However, I have listened to a lot of stories and experienced the system as a whole. 

Here are a few things to remember: 

  1. Housing is a human right. 90% of the time, once an individual gets into housing, their mental, emotional, and physical health improve. If you had to fight for your life sleeping on the streets every night… What would you be like? How would you interact with others? 

  2. Help looks different for each individual. Ask. Listen to what they need. 

  3. Socks and toiletries are the most requested items at homeless shelters. Drop some off next time you get a chance. Pads and tampons are vital, too. So is sunscreen. 

  4. Do no harm. Loneliness is the biggest factor in mental health deterioration. Don’t criminalize the houseless. 

  5. A lot of people struggle with housing instability, couch surfing and living paycheck to paycheck. Just because you don’t see the struggle doesn’t mean it is not there. 

“Love and compassion are necessities, not luxuries. Without them, humanity cannot survive.” —Tenzin Gyatso (Dalai Lama)

Do not make people feel unloved, worthless, or anything less than a human beings. We treat stray dogs better than we treat some people. It is not that difficult to make someone feel like they mean something. Buy someone a new pair of shoes, give someone a dollar, or even just offer a smile.

Everyone needs a little bit of hope.


Colleen Edwards loves burritos, writing, and camping. Until recently, she worked for Chicago’s Homeless Coalition to find housing for people who are in need. She hopes to one day write for National Geographic. Follow her on Instagram: @colleenedwards.

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