Documenters asked young people in Chicago about how they navigate finding work and career development opportunities.
by Grace Del Vecchio, Maureen Dunne, Eli Gillespie, Samuel Lisec, Monique Petty-Ashmeade, Jana Simovic, Camille Steinmetz, Caleigh Stephens, Molly Tinkey and Rubi Valentin
From left: Caroline Williams, Elsa Hiltner and Noah Tomko-Jones, three newly minted Documenters, gathered during orientation at the City Bureau office in Chicago’s Bronzeville neighborhood June 16, 2025. [Grace Del Vecchio/City Bureau]
In Chicago, the question continues to be raised: Where can young people be young?
It’s an issue making headlines most recently with the passage — and subsequent mayoral veto in June — of the controversial “snap curfew” ordinance. If implemented, the ordinance would have given the Chicago Police superintendent authority to impose a curfew for people under 18 years old with only a 30-minute verbal warning to disperse.
The ordinance was an attempted response to what has come to be known as “teen takeovers,” when large groups of young people gather downtown. Local officials have raised concerns about the “mass gatherings” escalating into fights, vandalism and violent crime.
The American Civil Liberties Union of Illinois, along with 19 other legal aid, civil rights and community organizations, wrote an open letter opposing the ordinance, raising legal and social concerns over the amendment and how it would be enforced.
Rather than heightened policing, community leaders and young people have repeatedly called for investment in third spaces in their communities — as well as increased job opportunities — as solutions to gatherings which could potentially end in violence.
To get more insight from those most directly affected, we asked Chicago Documenters under the age of 26 to interview their peers about how they navigate finding work and career development opportunities in Chicago.
Here are excerpts from those discussions. — Grace Del Vecchio
Interviews have been edited and condensed. Some names (marked with an asterisk) have been changed to protect the identities of interviewees who said they feared retaliation that could impact their jobs or student visas.
What do you find confusing or difficult about navigating work in Chicago?
Tatiana Sykes, 22, is a current Morgan Park resident and aspiring child psychologist. She cites working as both a day care educator and a resident adviser at Illinois Wesleyan University as core jobs that helped shape her career aspirations.
I feel like everybody’s hiring, but nobody’s hiring. That’s what gets me. Because if you have something that says you’re hiring now, and I fill out the application, and you never get back to me, what's the point of you saying you’re hiring? The least you can do is be like, “Oh, I'm sorry. We moved on to another applicant.” But so far, no one has done that to me, except for one person. So it’s confusing. Why are you hiring, but not hiring?
Alessia Antoine, 24, moved to Chicago from Miami when she was 18 to study at Columbia College. She now works at the Music Box Theatre in Lakeview and at Reckless Records’ location in the Loop.
I feel like jobs in general, not just in Chicago, often want you to have a certain level of experience to get the job. But you can't get experience if someone doesn't offer you that first opportunity. I don't understand how employers want me to know all this stuff, but no one will teach me. I don’t know what to do.
If I don't feel like a job is valuing me or my time, [or] they don't want me, then I don’t want to be there. And maybe this isn't the way to approach it. You should try hard. You should try to get jobs that you want. But it just feels like exerting so much energy into something that is not working out for me, you know? I just want to go somewhere that’s opening its arms.
Grace Bloom, 23, is a Chicago-based musician. Before moving to Chicago, Bloom lived in Tampa, Florida; and Cleveland, where she was also involved in the local music scenes.
A big difficulty for me is that my physical capabilities have changed a lot the past couple years. It’s hard to do a lot of these jobs that have more physical requirements. And there’s not really much information out there on how to ask for accommodations.
I think also in creative industries, especially, there’s such high demand, but there’s also less turnover, because once people get these opportunities, they want to stay in these jobs. Even if you’re qualified for a job, a lot of people who are overqualified for the job are unemployed currently.
I’ve been applying regularly since January, [and] I've gotten maybe three interviews. Most of it’s just ghosting and not even getting a formal rejection. So it’s hard to keep motivated when you’re putting so much out there, but not really getting much back.
Syed*, 25, is a computer science and music student at a local university, along with working as a musician, gas station attendant and bartender. He’s originally from Islamabad, Pakistan, and moved to Chicago in 2019 for school.
Accessibility is an issue for me, because not a lot of employers are very willing to hire international students. There’s also the question of whether the person wants sponsorship and stuff like that, which a lot of employers are like, “OK, I’d rather just not get into that.” Whenever I’ve interviewed for something, they've usually been like, “Are you an international student and would you require any particular form from us?” And, whenever I answer that, they’re like, “We don’t usually get students, but we may have a position for you,” and they haven’t really gotten back to me.
How have you been treated while on a job? Either by a boss, supervisor or patron. What were positive or negative experiences that stick out to you?
Sahian Hernandez Sotelo, 25, is a Mexican-American Latine from the Northwest Side of Chicago. They’re currently searching for full-time work after graduating with a degree in English from the University of Illinois Chicago in December. In the meantime, they are working as a server and STEM studio educator.
At one job, I have to hassle my boss for my pay, but that’s OK. Sometimes he doesn't send it right away, or there's not a consistent time he'll send it. I always get paid, but it can be frustrating at times. Because when I want my money, I want it now.
All my other jobs, besides my job at Aldi, have been overseen by male authority figures. Aldi was run by women. It was a beautiful environment to be in. I loved working there when it was women-run.
In other jobs, I was always trying to prove that I knew what I was doing — that I wasn’t just an airhead. It was a constant battle. Even in the food service industry, although it can be an easy job, they look at you like you don’t know what you’re doing, especially if you’re an attractive woman. A lot of the time, they see that first, and then they see you as an employee, and then they see that you’re, you know, an actual person who has a voice.
It was always very uncomfortable, because there’s always an inappropriate comment being made, but you can’t really say anything because that’s the higher-up, the manager.
Since graduating from the University of Illinois Urbana-Champaign, Nicholas Nevarez, 24, has spent the past couple years working at an immigration law firm. He is now looking for a new job — and overall guidance as he navigates the application process for law school.
I think there are pros and cons to the amount of autonomy that my boss is giving me. My boss has been very hands off in terms of overseeing the work that I do. It’s a bit complicated because I started this job expecting that he would be the one guiding me. But throughout the years, I’ve been talking more to his wife, who was also my boss.
And so I’ll tell her when I finish an application and she’ll review it. But sometimes, it'll take her weeks — or sometimes it’s been months — since I finished an application. I’ll finish a motion for court, and there’s a deadline, and when it doesn't get met, I have to remind her. If she still hasn’t done it, then I have to explain to the client why their work hasn’t been submitted. So that's been complicated.
What has also been complicated is the fact that the pay has been very inconsistent. I wasn’t really asking for my paychecks. I would go maybe a month or more, and, all of a sudden my boss would be like, “Oh, I haven’t paid you, right?” And I was like, no. So then he would pay me, and then I think he would get surprised by how much he would need to pay me, because he didn’t see how much work I’ve been doing because of how hands off he’s been. And then I guess he delayed paying me. This happened multiple times throughout the years that I’ve been with him, where I struggled to receive a payment from him, or other times he’s just completely not paid me for certain work that I’ve done.
How else did you spend time as a teenager? Did you participate in sports or other school-related activities?
Naylé Garcés, 23, is a Pilsen native and graduated last year from Loras College in Dubuque, Iowa. Equipped with her political science degree, she plans to pursue a law degree and become a lawyer.
Because my mom did work long hours, I had to find something to do after school. I did a lot of clubs or organizations in high school, like student government. I did this club called Las Chicas, an all-girls club where we talk about girl topics like our periods or we would just have various different activities about womanhood and girlhood. I really loved it. I was president of it, actually.
I had scholarships in high school, so I had a lot of activities that I would do for my scholarships, like I would tutor freshmen. I was just very involved in high school and, even in college, I was always very involved. Anything I could do to help, I would do it. I just loved being so involved, and it also helped me meet new people and get to know people that I didn't expect I would like and I ended up liking.
What are your thoughts on non-work opportunities for teenagers, including school-related activities or the availability of gathering places outside of school, home and work?
Maddy Hu, 22, moved to Chicago less than a year ago. When she’s not working one of her three jobs, you can find her rollerblading through the city or going on side quests with friends.
I’m a shift lead at The Butterfly House, and I have a 17-year-old working under me, so someone who’s very, very young, and he was working a lot of shifts. He hinted that his home life isn’t great, and that he can’t really go home, so he’s turning to work. I think there is respite in that.
But what are the non-work opportunities for kids to go out and be away from home? I don’t know how many opportunities that do exist, that are safe. I feel like, in general, there are a lot of spaces where there are just so many laws against loitering.
What do you expect kids to do? You want them to be outside, but they can’t loiter. That’s illegal. You've made it illegal to hang out outside. What do you want these kids to do?
What are some of your favorite or most important skills or experiences you gained through work?
Hannah Brody, 24, is currently a substitute special education classroom assistant with Chicago Public Schools, primarily working on the far North Side. They graduated college in 2023 and have had a difficult time finding employment in their field of urban studies and architecture.
Lately, I’ve been learning a lot as a substitute special education classroom assistants, and just working at CPS as a school assistant, which meant helping kids in the lunchroom and stuff. I’ve learned a lot about how terrible it is to keep school records, and how every piece of paper needs to go somewhere. It’s impossible to keep up with a never-ending task.
I’ve also learned a lot about working in special education. Above all, it has been kind of intuitive, but at the same time, I got no onboarding to work with high-needs minors. Not all of them are high needs — I just have been taking a lot of jobs at Chappell Elementary and realized that it was a school that had a severe and profound needs program, so it was kind of wild that I could just take those jobs and I got no onboarding.
What advice would you give to someone looking for a job on a college campus? Is there any advice you would give specifically to someone who isn’t a U.S. citizen?
Henry*, 24, currently works as a research assistant at a lab affiliated with a Chicago-area university. He came to the United States as an international student studying a scientific field. Since graduation, his visa has allowed him to work in positions related to his major. He talked about his experiences finding and navigating research positions as a recent college graduate who is not a U.S. citizen.
I would advise them to start with the people they know personally. That's how I landed my current position, and that’s probably why I was able to find an employer willing to pay me significantly more than what this position typically requires. People who know you are more invested and more willing to deal with the logistics and the paperwork of hiring you, especially as a noncitizen. That imposes more requirements and more hurdles. So I would definitely apply, for sure, through the job portals and to positions with people that you don't know personally, but definitely lean into your network and see if your [graduate program lead researcher] has friends that are hiring. That definitely helped me a lot.
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