After an introduction via the recovery home he was living in, Jesse begins his Cara journey with the October 2002 cohort.

“I figured I had nothing to lose. A few clients ahead of me were already attending Cara and sharing positive stories, so I decided to give it a try.”

After impressing staff with his dedication to and coordination in his job search, Jesse begins his Cara career as our first-ever Student Liaison.

“I created an organized job search system for myself — a binder with leads, processes, and follow-ups. Staff noticed, and we turned it into a system for all participants.”

Jesse is promoted to Assistant Trainer and teaches his very first class.

“My supervisor said, ‘Jesse, you know this stuff; why don’t you teach it?’ I acted surprised, but inside I was celebrating. I was nervous, but I had prepared myself for this moment. That class changed everything.”

Jesse is promoted to Trainer and begins building up the Training Department and codifying Cara’s curriculum.

“When I came through, the structure was still forming. It was more ad hoc. Over time, we grew organically — building curriculum as new challenges arose, adapting when participants struggled, and making improvements based on lived experience.”

Cleanslate launches and Jesse leaves the classroom to become the first hired employee of Cleanslate.

“I loved dressing professionally, and suddenly I was being asked to put on a lime green shirt and clean streets. But I trusted Cara, and I trusted the mission. So I said, ‘If this is what you need me to do, I’ll do it.’ It turned out to be one of the most transformational parts of the Cara story.

When Cara moves from the basement of Old St. Patrick’s Church, structures for Motivations began to form including the call and responses, the room setup, and the varying topics of the day.

“By 2006, Motivations became a well-oiled production. Done right, it’s corny as hell—and it absolutely works. You can feel the sincerity and the energy. It empowers participants and shows (not just tells) what transformation looks like.”

With the increasing number of people achieving one year on the job, the team ideates on a way to commemorate our graduates – leading to the creation of the Great Wall.

“We were seeing sustained success and wanted to display those names. Eventually we named the feature The Great Wall and added a monthly ceremony to honor those hitting one year on the job. It’s experiential proof. Peers can see what’s possible.”

After the success of Cleanslate’s launch, Jesse returns to the classroom as Director of Student and Alumni Affairs in Cara’s new permanent home at 237 S. Desplaines.

“My proudest accomplishment is the training team I’ve helped build. Their strength allowed me—for the first time in my career—to feel like I could step away and take care of myself.”

Cara begins celebrating new hires by announcing their job with the ringing of a bell in the Great Room. It becomes one of our most visible celebrations.

“I wanted a rallying cry for victories. I remembered, It’s a Wonderful Life, ‘Every time a bell rings, an angel gets its wings.’ For us, every ring meant a new beginning, a step toward self-sufficiency. The energy it creates is undeniable.”

Recognizing a desire from Cara graduates to remain connected, the Cara Alumni Association is founded. Today, they host three signature reunion events a year and continue to find ways to engage our growing alumni community.

“Many people found their community at Cara. The Alumni Association is only the tip of the iceberg—it can be extraordinary with continued participation and investment. Give people something worthy of belonging to, and they’ll keep coming back.”

At the first-ever Cara Gala, the Jesse Teverbaugh Distinguished Alumni Award is created and presented to Jesse by Cara founder Tom Owens. Ten other Cara alumni who exemplify this work have since received this honor.

“The award’s not about me. It honors distinguished alumni who embody Cara’s five ways to transform your life—those who walk the walk, applying our principles to real life in visible, inspiring ways. The hardest part is choosing just one each year—there are so many who deserve this recognition.”

The first Next Steps ceremony is held—which recognizes job seekers who have completed our core competency training and moving onto their job search process with our corporate partners.

“It’s not just for the person being honored; it’s for everyone still straddling hope and doubt, thinking, ‘I can’t wait until that’s me.’ I remember how depleted I felt as a participant—any flicker of hope mattered. These rituals create that spark.”

The Road Up, a documentary filmed in 2016 that follows four job seekers on their path out of poverty at Cara, has its premiere. The film would hit the festival circuit, screening everywhere from Chicago to Melbourne, Australia.

“The Road Up is a living document. I’d seen so many miracles in that classroom—things hard to explain without witnessing. I wanted the world to see it. My worry was that it would be scripted or inauthentic. What you see is exactly what happened—first take, real time.”

With the COVID-19 pandemic, Cara Collective was forced to suspend in-person programming for the first time in our history. During that time, pivots were made to virtual training and transformations continued to happen. In January 2022, we excitedly reopened our doors for fully in-person, cohort-based training again.

“That time was bittersweet. The Great Room felt empty. Honestly, it was part of why I delayed retiring—I promised our leadership I’d help restore the true DNA of Cara before I left. It took detailed work and coaching (for staff and participants), but today you can feel it again.”

Jesse Teverbaugh retires, closing the chapter on a 23-year career, 200 cohorts teached, and more than 20,000 lives transformed.

“Without Cara, I don’t think my legacy, self-awareness, and sense of belonging would be what they are. I lost a lot once—mostly material things—but I gained the chance to reinvent myself and to help thousands reinvent themselves, too. What I’ve received back—in relationships, meaning, and impact—is tenfold. The pain was real. The purpose is greater.”