WATCH: ‘I wouldn’t have made it without StreetWise:’ How one organization provides jobs, support for those experiencing homelessness

StreetWise vendor A. Allen sells a magazine to a customer. Allen has worked for the organization for about 13 years and credits it with helping him maintain his sobriety.
StreetWise vendor A. Allen sells a magazine to a customer. Allen has worked for the organization for about 13 years and credits it with helping him maintain his sobriety. (King Jemison/MEDILL)

By King Jemison
Medill Reports 

Experts estimate there are 68,000 Chicagoans experiencing homelessness right now. This crisis may be worsening. 

That’s where StreetWise comes in. Hear incredible stories of how the organization has helped the unhoused for nearly 32 years — and why it continues to be so essential. 

KEITH HARDIMAN, StreetWise vendor: StreetWise has been a tremendous help. 

JEMISON: That’s Keith Hardiman. He’s experienced homelessness for much of his adult life. But about 20 years ago, he became a StreetWise vendor. He credits the organization for helping him turn his life around. He’s not alone.

A. ALLEN, StreetWise vendor and field supervisor: I’ve been with StreetWise going on like 13 years. It’s been a wonderful experience. 

RUSSELL ADAMS, StreetWise vendor: StreetWise, this is my job. I mean, I take this very seriously. 

SYLVIA SPIVEY, StreetWise vendor: Thank God I don’t go a day hungry, I’ll put it that way. 

JEMISON: StreetWise creates news magazines centering the experience of the unhoused. New vendors get 15 free magazines. After that, they can buy them for $1.15 each and then sell them for $3. Some of the vendors say this opportunity has changed their lives. 

HARDIMAN: Well, ever since then, I haven’t been broke. 

ADAMS: Because I was homeless. I had no money, nowhere to stay. I found StreetWise. Eventually, I figured it out: how to save money, get me a place to stay and do the right thing

ALLEN: And this has been keeping me sober. Every time I thought about getting high or drinking, I would come out and sell StreetWise. 

ALLEN [SELLING STREETWISE]: StreetWise, how you doing, ma’am? Hey, how about you, how you doing?

JEMISON: The need for StreetWise is perhaps greater than ever. The Chicago Coalition for the Homeless estimates there are 68,000 people experiencing homelessness in Chicago today. That number may be going up. 

JENNIFER KOUBA, DePaul University adjunct faculty: I feel like street homelessness is the worst I’ve seen it in the last 10 years. 

MOLLY BROWN, DePaul University associate professor: We’re also seeing incredible increases in rent prices and general inflation. Wages are simply not keeping up with that. This is a crisis that will continue to worsen unless we put some real money forward to address homelessness. 

JEMISON: I’m outside the StreetWise office in the Near South Side. And here, the StreetWise mission goes beyond just selling magazines. Because here, vendors can get a hot meal, a clean bathroom and, above all, a sense of community.  

JULIE YOUNGQUIST, StreetWise Executive Director: This is really the center, the heartbeat of StreetWise. And unfortunately, homelessness, people feel is a personal failing. And so there’s a lot of judgment and misperceptions that go around that. But when they come here, all of those misperceptions fall away. 

AMANDA JONES, StreetWise Director of Programs: We have one of our vendors that said this is the last house on the block. When there’s no other place to go, you can come here. 

JEMISON: One of the most powerful aspects of StreetWise is that it builds connections between vendors and the surrounding community. 

HARDIMAN: My favorite part is the people. The expressions, the smiles, that does me a lot of good. 

HARDIMAN [SELLING STREETWISE]: Good morning! Happy Friday! 

BROWN: So by having these day-to-day interactions with StreetWise vendors, it can paint a slightly different picture for the public of, “Unhoused people are just like us.” 

JEMISON: Experts say one of the keys to ending homelessness is building empathy for the unhoused. 

KOUBA: It’s easy to ignore that and think, “It’s not my problem.” Paying attention and thinking of people experiencing homelessness as our neighbors rather than “the homeless” is a big part of it.

JEMISON: In reality, many people throughout the city are living on the brink of homelessness. 

BROWN: About 50% of Chicagoans are living rent-burdened right now. Homelessness is becoming a threat to a large swath of Chicagoans.

JEMISON: StreetWise is by no means a blanket solution to this problem. But speaking to vendors, it is clear that working for StreetWise can restore a critical sense of confidence and dignity. 

ALLEN: My life became different because, first of all, StreetWise is a responsibility, when you talking about being your own boss. 

ADAMS: Hey, I’m a businessman! 

JEMISON: The StreetWise motto is “a hand up, not a handout.” For some of these vendors, that hand up might have saved their lives. 

ADAMS [IN STREETWISE OFFICE]: Thank StreetWise. Without StreetWise, I wouldn’t be here right now. I wouldn’t have made it without StreetWise. Thank y’all. 

JEMISON: StreetWise has played a part in countless stories like this over nearly 32 years. In Chicago, I’m King Jemison for Medill Reports.  

King Jemison is in the sports media specialization at Medill. You can follow him on X @king_jemison