The CARA Collective, an innovative Chicago workforce development nonprofit founded in 1991, is currently ending its third decade of helping Chicago residents find ways back into the workforce by giving them hope and developing the skill of persistence. CARA’s clients’ struggles and successes coming back from homelessness, incarceration, and addiction, are reflected in The Road Up, a new documentary by Greg Jacobs and Jon Siskel.

The film is also a reminder of CARA’s multiple early connections to leaders from River Forest. Eric Weinheimer served as CARA’s CEO for 18 years, from 1996 to 2014 (Weinheimer is currently on the board of Growing Community Media, the nonprofit owner of Wednesday Journal). Mark Carroll took a one-year sabbatical from Goldman Sachs in 2005 and arrived at CARA to launch Cleanslate, a business within CARA that created jobs for clients not readily hired by private enterprises due to their criminal records. Kristin Carlson Vogen, former executive director of the Oak Park-River Forest Community Foundation and now at the Chicago Community Trust, was a longtime CARA board member.

Those local ties are one reason the documentary will have a free screening at 7 p.m., Dec. 2, at the Lake Theatre.

The film follows four job trainees over a two-year period, detailing their experiences with CARA and the job market. At the center of the movie, though, is Jesse Teverbaugh, director of alumni and student affairs, affectionately known as “Mr. Jesse.” According to Jacobs, “Jesse is really the core of the film. So much of the film takes place in the class that he teaches. He’s responsible for what’s kind of the ‘boot camp’ part of the program, where everybody has to take this month-long class called ‘Transformations.’ Jesse is really one of the greatest teachers I’ve ever seen in action. It’s amazing the way he connects with everybody in that class. People are coming from all backgrounds and they’ve all had different challenges; they’re at different low points in their lives. His job is to spark something to give them the sense that maybe, just maybe, there’s some hope. That’s the kind of thing that will keep them getting out of bed, keep them showing up, and turning that hope into a habit.”

Using a combination of genuine concern and tough love, Teverbaugh continually pushes students to give better than their best. Despite being front and center, leading the charge, hardly anyone has felt the need to challenge his dominance, which was well-earned.

“If you go to CARA, you have to want to change your life,” says Jacobs. “Because of that, people are going in, and they are vulnerable enough that when they see someone like Jesse who is really putting himself out there to help them, they want to respond.”

Despite the respect, Teverbaugh still works hard to sustain his impact. “A lot of people in the class every month are people who, because of their experiences, it’s incredibly hard for them to trust,” Jacobs says. “So he has to both be an authority figure and be somebody that they can believe and buy into. It’s a really delicate balance to strike. There are always people who are going to challenge and be a struggle for him to win over. It’s one of the reasons why he treats it like a boxing match each month. One of the first times you see him in the film, going into the classroom from the back, it may remind you of the boxer going into the ring. He just exhausts himself. By the end of the four weeks, he is completely spent.”

The age range of students varies, from early 20s to early 60s. The various stumbling blocks these individuals have to move past varies.

“It’s people who, as Jesse puts it, have ‘lost their mojo’ in some way or another,” says Jacobs. “It can be addiction or incarceration or homelessness. But it can also be a marriage ended and you’ve just kind of sunk after that. Or there was a financial problem and things spiraled out of control. It doesn’t have to be those kind of big categories, but it often is.”

This movie also introduces us to Clarence, Kristen, Alisa and Tamala, four graduates of the class who are shown putting the lessons to work. Jacobs notes, “We followed them over the course of the next two years — not constantly, but staying in touch with them and going out and filming, occasionally, seeing the challenges and the obstacles they faced,” along with “the internal and external barriers that keep people from being able to get steady employment. It’s really a powerful thing to watch people overcome both. For all these people, the story never ends, because it’s a constant up and down. The good thing is, so far everybody has found some measure of stability.”

Free screening at the Lake

The Road Up will have a free screening on Dec. 2 at Oak Park’s Lake Theatre. Following the 7 p.m. screening, there will be a Q&A with Kathleen Caliento, CARA CEO; Jesse Teverbaugh, CARA’s director of student and alumni affairs, and Siskel and Jacobs, the film’s co-directors.

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