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Jessica Whittaker drives a bus for the Omaha Regional Transit Authority through the same city where she committed her crimes. She got there, she will tell you, by way of a phrase: “Can you Amy this?”

“Oh, look at you. You’re a little girl, you’re short.’”

That was what one of the men in the room with Whittaker said during a class in Southeast Community College’s UPWARD program. She was training for her commercial driver’s license alongside four other students. By the end, she was the only one of the five who finished.

“I looked at him and said I’m going to be here,” Whittaker said. “At the end, I was literally the only person who made it.”

Whittaker grew up in Omaha, raised by a single mom with six kids. She joined the military as soon as she could, but got kicked out and went to jail for robbery at 18. After her release, she had a child and was incarcerated again on drug charges.

This time was supposed to be like the last: keep her head down, do the time, and get out. But it wasn’t. She fought a lot. Then she got the news her son was diagnosed with Asperger’s Syndrome.

“I can’t do this,” Whittaker remembers thinking. “I can’t tell him not to let the world beat him up while I’m letting the world beat me up. I started taking classes and ultimately ended up in work release where I met Amy Doty.”

Doty, the dean of UPWARD, would become the gravitational center of Whittaker’s next chapter. She introduced her to the UPWARD program, and asked her point-blank about getting her CDL. Doty told her she would pass. So Whittaker showed up. For every class.

Every morning at 8 a.m., they drove her from work release to the Milford Campus. She spent every day on the road—to Lincoln, to Omaha, to small towns nearby.

It was Doty who took her to get her driver’s license and Doty who attended her graduation. When Whittaker got sent back from work release and didn’t get her photo taken for her license, Doty arranged to have the DMV take her photo at the prison.

In the Whittaker household, that kind of move had a name: “Can you Amy this?”

“Amy has this thing, where I say ‘Can you Amy this?’ and she does it,” Whittaker said. “And, oh my god, she hasn’t failed me yet. Anytime she asks me to do anything, anything she has ever stood behind, I’m 100% with it.”

After graduating from the program, Whittaker found a job with Grand Island Express driving over the road. They agreed to train her and she finished their six-week training program in under three. She spent most of 2025 driving a semi.

But coming home for Thanksgiving, she could see the math wasn’t working—two or three days a month with her family. She needed to be home. She needed a different route.

She found one driving a city bus for the Omaha Regional Transit Authority.

“I work for the city bus in Omaha. The same city I committed my crimes in, I now work for,” Whittaker said. “It is amazing what second chance opportunities will do.”

Now Whittaker is one of UPWARD’s most public advocates. She talks about the program as a voluntary one—about how the moment a student signs up is the moment they’re declaring they want to invest in themselves. Thanks to people like Doty, Whittaker also knows SCC will give students the tools they need to be successful in whatever comes next for them.

“I’m watching other people become chefs and CDL holders, and it is just leaps and bounds on changing for people to not become incarcerated again,” Whittaker said. “Nobody would know I was in prison. They can’t even look at me and imagine that. I’m just a regular person again, and that’s really all I wanted. I feel like when you serve your time, you should get that.”

Damon Bennett
Activities Information Director
402-437-2077
dbennett@southeast.edu