Skip to main content
Move the World.
Transitional employment

It's a muggy Wednesday morning in Chicago's Wicker Park neighborhood, the temperature and humidity rising before the sun. Lena, decked out in her eye-catching slate shirt and chartreuse vest, leans slightly out into the busy rush-hour traffic, sweeping litter (wrappers, cups, lots of cigarette butts) from the gutter into her dustpan.

On the sidewalk, she empties her collection into a cart. As she moves down the street, cleaning curbs, sidewalks, planters, empty patios, and even under the grates around sidewalk trees, she greets the Chicagoans walking by.

transitional employment
Lena, an intern at Cleanslate in Chicago, spends her time making sure the streets are tidy. Credit: B. David Zarley

Lena is an intern (read: crew member of a cleaning team) at Cleanslate, a neighborhood beautification and landscaping business. Cleanslate offers transitional employment opportunities and is operated by Cara, a nonprofit that has been working in the city since 1991. 

Cara provides job training - such as resume workshops and mock interviews - and connections for people looking for work. This includes everything from jobs for felons, those dealing with domestic violence, addiction recovery, poverty, housing instability, and other missteps or misfortunes. 

"You'd be Surprised by What You Find in the Cans"

The work isn't terribly glamorous, but Cleanslate offers interns hands-on experience, a paying job, and work skills that go well beyond sanitation techniques. These transitional jobs can be a bridge on resumes and, for some, the beginnings of an employment history. Gott likens the job search to sports' free agency: if you were not on somebody's roster, other teams just won't be as interested. If you're already on a team, the likelihood of another coming calling is a lot higher.

Out on the street, Cleanslate teams remove trash and empty cans on neighborhood routes, power wash graffiti, and do snow removal. In crews of four to seven people, led by a crew chief, they handle up to eight routes across Chicago in a typical day. Crews meet at 7:15 a.m., sharp - punctuality is a must, Lena says - and move down their streets, cleaning as they go. 

For people like Jeremy, getting a job with trust, responsibilities, and even management can seem like a pipe dream. But since he started at Cara, he has bought a house and found stability.

Cleanslate teams are commissioned by city aldermen, neighborhood chambers of commerce, local businesses, or for special events: at the Mexican Independence Day Parade, Lena followed the horses.

Lena has been with Cleanslate for a few months. She had been a security guard at a local grocery store but decided she wanted to advance her career elsewhere. At Cara, she got help rewriting her resume and interviewing, and she's already spoken with a hospital and a transit police agency. In the meantime, Lena works her routes for Cleanslate. 

"You get hands-on with the job," Lena says. "Cleanslate (and Cara) do a good job, and let you know ... how to conduct yourself." As part of a crew, the interns learn teamwork, but along their routes, without the crew chief looking over their shoulders, they also learn how to self-motivate and work independently.

“You’re building out the whole person. You’re trying to give them access to flourish and become themselves, and take personal responsibility and really own their life.”

Brady Gott , Managing Director of Cleanslate

What makes Cleanslate different from other transitional employment opportunities is that it takes a holistic approach to job counseling, offering workshops and training on deeper developmental and emotional skills, like forgiveness and confidence.

transitional jobs
Lena works her way down Division Street in Chicago’s Wicker Park. Credit: B. David Zarley

"You're building out the whole person. You're trying to give them access to flourish and become themselves," says Cleanslate's managing director Brady Gott, "and take personal responsibility and really own their life."

As she moves down the street, Lena fills one of the trash cans on her cart. A block or so from the intersection where she started, she empties the first sidewalk can on her route: this one is overflowing, with bees circling it like electrons. 

"You'd be surprised what you find in the cans," Lena says - needles, bees, maggots, one never knows. 

With her new haul collected, Lena moves the full bags to her other can, which will be periodically collected by her crew chief, Jeremy, in his pickup truck.

"It's Actually for the People That Want to Change"

Jeremy stands in the bed of his Cleanslate pickup, tossing bags collected by his crew into a space at a city dump. Ferrying away full bags is just one part of his job as crew chief: his truck is always in motion (whenever he isn't standing in the back of it). 

transitional jobs
Jeremy empties the bags of trash collected by workers like Lena at the city dump. Cleanslate has given Jeremy the opportunity to work hard and thrive. Credit: B. David Zarley

He swings by to see if everything is going alright and helps to smooth over any issues on the street - one person on this route has a tendency to set trash cans on fire if his possessions are moved. He motivates and instructs the interns, as well as making sure Cleanslate's contract requirements are met.

Jeremy is himself an alumnus of Cara. He came to the organization six years ago after being released from prison. While talking inside with a fellow inmate about his desire to put his life together and find work - something that's often difficult with a criminal record - another inmate interjected and told him about Cara. Jeremy went to the South Side campus and has worked his way up to crew chief.

“If you’re ready for change, this is the place to come. And they will get your life on track.”

Jeremy , Cleanslate crew chief

Jeremy says there's a deep sense of pride when he sees an intern thriving in a job. For people like him, getting a job with trust, responsibilities, and even management can seem like a pipe dream. But since he started at Cara, he has bought a house and found stability.

"I did something within five and a half years that I didn't do my whole lifetime trying to chase the fast money," he says.

Cleanslate doesn't have any magic potions: interns have to be ready and willing to work and learn, Jeremy says. "It's actually for the people that want to change," he remarks, as he wheels his pickup through an intersection to meet up with his crew members.

"It's not a game here ... if you're ready for change, this is the place to come. And they will get your life on track."

Subscribe

Explore More Stories

Catalysts
This Nonprofit Gives Bikes and People New Life
This Nonprofit Gives Bikes and People New Life
Catalysts
This Nonprofit Gives Bikes and People New Life
Working Bikes has spent nearly two decades rescuing bicycles from the waste cycle to give people purpose, access to jobs, and independence.

Working Bikes has spent nearly two decades rescuing bicycles from the waste cycle to give people purpose, access to jobs, and independence.

Catalysts
The Crib: A Place to Call Home
The Crib: A Place to Call Home
Catalysts
The Crib: A Place to Call Home
For young LGBTQ adults, this is the shelter that accepts many people that are too often turned away.

Every night, young adults pass through the basement door of the Lakeview Lutheran Church, close to the heart of Boystown, the gay neighborhood-within-a-neighborhood on Chicago’s North Side. Like many institutions in Lakeview, the church offers a place specifically welcoming to the LGBTQ community. These young adults are taking refuge at The Crib, an overnight emergency shelter for people aged 18 to 24 who find themselves temporarily homeless. Founded by The Night Ministry in 2011, The Crib is one of the few places in the city where young LGBTQ adults, especially those of color, can find housing and community with others their age in similar situations.

Catalysts
This Woman is On a Mission to Turn Beer into Food
This Woman is On a Mission to Turn Beer into Food
Catalysts
This Woman is On a Mission to Turn Beer into Food
Jacquie Berglund is using the profits from her beer company to buy organic produce from local farmers and distribute the produce to food banks in the area.
By Teresa Carey

Jacquie Berglund considers herself more of a wine drinker than a beer drinker, yet she is building an empire around the beer brand, Finnegans. When Berglund purchased the brand for only a dollar, she knew that if Finnegans were to make an impact, the beer needed to be in every pub in Minnesota. Now you can find Finnegans in four Midwest states. But Finnegans is more than a beer company. From combating food insecurity to...

Building Community
This Chicago Urban Farm Grows Opportunity, Jobs
This Chicago Urban Farm Grows Opportunity, Jobs
Building Community
This Chicago Urban Farm Grows Opportunity, Jobs
Growing Home’s organic urban farms use agriculture as a vehicle for providing job training for people with...

Growing Home’s organic urban farms use agriculture as a vehicle for providing job training for people with employment barriers, whether due to prior convictions, medical concerns, poverty, homelessness, or any other issues which make gainful employment difficult.

#fixingjustice - Re-entry
24 Years For a Crime He Didn’t Commit
24 Years For a Crime He Didn’t Commit
Watch Now
#fixingjustice - Re-entry
24 Years For a Crime He Didn’t Commit
When a prisoner serving a life sentence is suddenly found to be innocent, it often makes national news. But what happens after the cameras go away?
Watch Now

There are around 2,200 exonerees in the U.S.—people who were convicted of a crime and then later proven innocent by their own doggedness or new evidence in a case. When they are freed from prison, their lives are often saddled by the same issues that hold back people who actually committed a crime—lack of education, no job skills or employment history, and the stigma of having spent years in prison. While their release is...

Steven Pinker Makes the Case for Optimism
Steven Pinker Makes the Case for Optimism
Watch Now
Steven Pinker Makes the Case for Optimism
Are things really worse than ever, or are we missing the bigger picture?
Watch Now

Author and Harvard professor Steven Pinker lays out what he see as a basic paradox. The news today seems worse than ever - but based on a number of key metrics, Pinker argues the world is better than it’s ever been. Pinker explores the data and makes the case for how can we tackle the world’s problems while not drowning in negativity. That’s the focus of his latest book, Enlightenment Now: The Case for Reason, Science,...

Coffin-Building Club Helps Seniors Face Death and Enjoy Life
Coffin-Building Club Helps Seniors Face Death and Enjoy Life
Watch Now
Coffin-Building Club Helps Seniors Face Death and Enjoy Life
These seniors are tackling the stigma around death by decorating their own coffins.
Watch Now

Most people are afraid to even talk about death, but New Zealand’s Kiwi Coffin Club is facing it head on. Founded by Katie Williams, a former midwife and hospice nurse, members build and then decorate their own customized coffins as a way of celebrating their lives and highlighting their unique personalities. "Death's pretty natural, you know," says Williams. "It shouldn't be a frightening sort of situation. It's part of...

Dispatches
The Eternal Sunshine of the Stressed Out Mind
The Eternal Sunshine of the Stressed Out Mind
Dispatches
The Eternal Sunshine of the Stressed Out Mind
Researchers at Cambridge University have finally figured out how the brain stops stressful thoughts and memories...

Researchers at Cambridge University have finally figured out how the brain stops stressful thoughts and memories from taking over our minds.