Policy & Practice | Fall 2026

Back to the Future: Bridging the Technology Gap for Returning Citizens the human in human services By Ricky Hamilton

W e’re entering an era where a job search starts with a keyboard and entire industries get reshaped by artificial intelligence (AI) in a matter of months. That shift disorients most people already in the workforce. For someone coming home after decades in prison, it can be disqualifying before they even start. I saw this up close with Seneca Allen, my company’s most recent hire. Seneca taught himself to design flyers and run marketing campaigns using AI while still living in a work release center—no institutional support, no formal training. After 20-plus years inside, he lacked basic computer skills at first. A little coaching closed that gap fast, largely because AI itself was what he’d already taught himself to use. If someone can build that much from nothing, the real question isn’t whether returning citizens can adapt to an AI-driven labor market. It’s what becomes possible once we actually build the pipeline that lets more of them try. I know that gap personally. For 18 years, cassette tapes were the most advanced technology I had access to. CDs and mp3 players came and went without me. Computers and tablets—the basic tools everyone else uses to search for a job, learn a skill, or stay connected to the people they love—were off-limits for most of my sentence, until I reached a facility called Kewanee Life Skills Reentry Center. The justification at every other institution was safety and security. But safety doesn’t explain why a person should walk out after 20 years having never touched a keyboard, into a labor market that assumes everyone has.

Kewanee opened in 2017 as the first facility of its kind in Illinois, and I spent the last four and a half years of my sentence there. It’s where I became a teaching assistant for a manufacturing class and learned robotics ( https://www.youtube.com/ watch?v=4GPfU7Skth8 ). It’s where I finished the last few hours of my associate’s degree. It's also where, alongside my now-business partner Michael Cannon and psychologist Jim Estes, I helped build TWO ROADS ( https://idoc.illinois.gov/news/ tworoadse-zine.html )—a platform where we wrote articles, edited video, and produced a podcast, all from inside a facility. Nothing broke when they gave us real tools. People wrote, taught, and learned. The barrier was never really about safety. It was a system that had made restriction the default when it should have been the exception. Kewanee is also where GOT JOBS America started. Michael and I were in the first Defy Ventures/PERC entre preneurship cohort in Illinois—eight months of curriculum that end in a pitch

competition, with executives riding a bus down from Chicago to hear incarcer ated men defend a business plan. Ours was GOT JOBS America. We wrote it in a classroom, pitched it there, and walked out with it. The company making this case is one that was built inside the same system it’s trying to change. None of that pointed me toward the skilled trades my manufacturing and robotics training might have suggested. It pointed me toward reentry work— using lived experience to guide people through the part of reentry that matters most and gets talked about least: navigation. Knowing what door to walk through next, who to call, which program actually helps versus which one just looks good on paper. I had to learn that by living it, then learn how to teach it. I came home to job offers already waiting, based on work I’d done while still incarcerated. I chose Phalanx Family Services instead, specifically for a program called The Road Home—the first court-, county-, and state-funded reentry program of its kind. I started there

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