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The Working Poor - A Week With Chicago's Homeless

“Some people are so lazy. Why can’t they just get a job?” It’s a common sentiment I hear from people who learn that I’m on the Board of an organization that helps Chicago’s homeless.

Unfortunately, it’s also misguided. As the Chief Revenue Officer of a billion-dollar software company, I’m familiar with hard work. And if “being lazy” was the primary cause of homelessness, I probably wouldn’t be interested in getting involved. Yet I’ve taken a closer look at the issue, and know there’s a lot more to the discussion.

The Chicago Coalition for the Homeless conducted a study which found that 18,000 homeless people in the city have completed some college and 20% of Chicago’s homeless have some form of employment.

Yet a variety of factors prevent the working homeless from securing housing.

Even When Employed, It’s Hard To Get Out of Homelessness

Jetaun completed a welding training program and landed a job at a Chicago manufacturing plant – yet the $1,000 security deposit required at the apartment she wanted to rent was a blocker that kept her and her son homeless.

It’s a common challenge – researcher Barbara Ehrenreich found that low paid workers – including restaurant hostesses, hotel housekeeping staff, and Walmart workers – often are challenged to save enough money from their hourly wages to get the typical “first and last month’s rent” required for apartments that they could otherwise afford. Lacking an apartment, workers may turn to motel or hotel stays – whose nightly rates add up to more than what their monthly rent would cost, continuing to prevent them from amassing a security deposit and getting out of homelessness.

Unexpected medical expenses are also a key contributor to employed people becoming homeless. NerdWallet found that three in five personal bankruptcies in the US are due to medical bills, while the Kaiser Family Foundation found that privately insured people who had out-of-pocket medical expenses that exceed five percent of their income are about twice as likely to have difficulties paying their rent and utilities. These working folks look like the rest of the employed population, so aren’t as easy to identify as “homeless,” but are nevertheless a key constituency we need to serve when we talk about homelessness in Chicago.

Homelessness Makes It Hard To Stay Employed

The working homeless also often have challenges in keeping their job, due to limitations that homelessness presents. Just about every job requires employees to have clean clothing and maintain good personal hygiene – and this is especially true in the service industries that typically hire unskilled hourly workers (almost 12% of all jobs available in the US are in the retail sector, which includes food service).

Homeless individuals often lack ready access to shower and laundry facilities – making it difficult for them to be able to meet this minimum standard of cleanliness required to keep their jobs. Yes, there are some public showers, laundromats and toilets throughout the Chicagoland area, but membership fees at gyms are often prohibitively expensive for the working homeless, and the owners of fast-food restaurants and stores often lock their restroom doors and limit their use to paying customers.

Being homeless also creates a lot of mental and physical stress that also can impede a worker’s performance. Aside from their day job, homeless people need to deal with a host of activities – including visiting government agencies, attending food services, finding shower and rest room facilities, and more – while depending on public transportation or (in the event that they can’t afford a transit card for the day) – walking. As a result, the homeless worker is challenged to get the full amount of regular rest and sleep required to function effectively at work. People living outside a home also lack personal safety, and need to stay vigilant of their surroundings at all times - meaning that the hours they do manage to get sleeping are often not completely restful.

Securing a Job Is More Difficult When You’re Homeless

If you’ve ever been unemployed, you know the desperation and difficulty you feel in finding a job. For homeless workers who have lost their jobs, the circumstances of their homelessness only compound the difficulties – making it seem nearly impossible to find employment.

Even the most entry-level jobs require some form of identification in the hiring process, which also practically requires an address to receive mail at. For the higher-paying, skilled jobs that the 18,000 college educated homeless might covet, credit checks and arrest records are also often part of the pre-hire qualification process. And the very nature of homelessness – sleeping in a car parked in the wrong place, or on a bench in a public park – makes the homeless individual a target of police.

The challenges of personal hygiene and access to clean laundry and interview clothes that make it hard to keep a job also are limiting factors in participating in interviews and securing a job.

What We Are Doing

At Care For Friends, we connect Chicago’s most vulnerable with the resources they need to achieve a better quality of life. With 15,000 homeless contact per year, we create a community that doesn’t just connect Chicago homeless with basic needs like food and hygiene, but also connection to job training, housing, and better mental and physical health.

Our homeless youth initiative also provides a venue for nearly 300 of Chicago’s homeless students to have a safe place to study, receive tutoring, and prepare for college exams. Partnering with DePaul University, we have a goal of getting three of them enrolled in college next Fall.

To support these initiatives, we will be hosting our annual “Sleepout For Homelessness” where we plan on having 200 individuals spend one night with us to fund a year’s worth of programming. Learn more about the event (and sign up as a sleeper, supporter, or volunteer) at

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