How Sierra Robinson Is Breaking the Cycle Of Incarceration

Sierra Robinson’s story begins where too many do: with generational incarceration, an unstable childhood, and a justice system that saw her coming.

A Childhood Shaped by Systemic Cycles

“I was three when both my parents were locked up for selling drugs,” Sierra Robinson began in a recent interview. “That’s when I went into foster care.”

Sierra’s early life was marked by instability—bouncing between homes, struggling to feel safe, and witnessing her parents’ continued battles with addiction after their release. “They were still addicted. My mom would disappear for days. I never really knew where she was.” She adds, “People used to tell me all the time, ‘You’re gonna end up in prison just like your parents.’”

By the age of 17, society’s vision of Sierra’s future had become a reality. Sierra was involved in a robbery where someone lost their life. At 18, she was sentenced. “I felt like I wasn’t a good person. I thought I was just going to be a career criminal.”

Her story echoed the expectations placed on her. Once inside prison, Sierra found something she hadn’t expected: a path that would lead her not only out of incarceration but toward a life of purpose and leadership.

Sierra’s life began as another statistic in the cycle of generational incarceration. It quickly became a story about breaking the cycle of incarceration through education, mentorship, and self-belief.

Redefining Possibility Behind Bars

At first, Sierra didn’t see a way forward. “When I first got to prison, I was hopeless. I didn’t think I’d ever get out,” she says. “I didn’t think I could do anything different with my life.”

Things began to shift when she joined Televerde, a program that employs incarcerated women in business development roles. Her supervisor, Ron, played a pivotal role in reshaping her perspective. “Ron was the first person to talk to me like I had a future. He treated me like I could be somebody,” she says. “That helped me stop seeing myself as just a criminal.”

Soon after, Sierra started hearing about The Last Mile (TLM) from a close friend on the inside. “She would tell me about learning coding, CSS, HTML—all these things I didn’t understand,” she says. “But I could see the joy on her face.”

“I Didn’t Think I Belonged”

At first, Sierra believed she didn’t belong in the TLM classroom. She turned down the opportunity to apply twice. “I didn’t think I belonged there. I thought I wasn’t smart enough,” she admits. Finally, the Director of Education personally encouraged Sierra to give it a try. That third offer stuck, and she applied for The Last Mile.

Once she enrolled, the change was almost immediate. “I was reading books and reflecting on my life. I was thinking differently,” she explains. “TLM taught me that I was capable of more than I ever thought possible.”

This moment marked a turning point. She was no longer defined by her past, her prison sentence, or societal stigma. Sierra was now defining her own future in a classroom of life-minded students and facilitators.

A Program That Feels Like Family

Sierra refers to her time in The Last Mile as completely transformative. “I didn’t expect to feel so seen,” she says. “The classroom was filled with people who had stories like mine. We weren’t talking about what we did in our past—we were all talking about who we wanted to become.”

She quickly bonded with instructors like Terrell Lemons, Henry Dillard, and Brett Buskirk, all of whom are TLM alumni and returned citizens. “The instructors really invested in us. They believed in us. They didn’t look at us like we were broken.”

Sierra completed the full curriculum, despite COVID-19 extending the program’s length. “We were in class longer because of the pandemic,” she explains. “It actually worked in my favor. I had more time to really learn.”

After graduating, she continued her growth and served as a Teaching Assistant. “That’s when I really started to see myself differently. I wasn’t just a student anymore. I was helping other people understand their potential.”

Eventually, she was transferred to a lower-security prison. Without daily access to TLM’s program, she feared she might lose the skills she had gained. “I hadn’t coded in almost a year. I thought I lost it,” she says. “But I held on to the mindset I learned in class. That made all the difference.”

The environment she experienced at TLM was unlike anything else in her incarceration. “It felt like family,” she says. “And that stayed with me, even when I left.”

Returning Home, and Returning to The Last Mile

Sierra was released in October 2023, unsure of what her life would look like. “I didn’t have a job, I hadn’t touched code in a year, and I was scared,” she says.

One of the most important services The Last Mile provides to recently released Alumni is pairing them with an Alumni Success Coach. This person serves as an advisor and valuable resource to returning citizens who may otherwise struggle to find stability and employment after their release from prison.

It was in a conversation with her own Alumni Success Coach that Sierra learned about an offsite TLM event in Indianapolis. “He told me about the event and encouraged me to apply for a job at The Last Mile,” she recalls. “I was like, ‘What? Me?’”

Still filled with doubt, she applied for the Academic Success Representative role. “I didn’t think I would get it. I thought I hadn’t coded in a year. There’s no way,” she remembers.

Two weeks later, she interviewed with two previously incarcerated members of the TLM team. “They didn’t make me feel like I had to prove I was good enough. They made me feel like I already was,” she says.

The offer came shortly after. “Three weeks after I came home, I had my first job offer. I cried. It was the first job I ever got in my life.”

That moment was a milestone, and working for The Last Mile proved to be a full-circle moment for Sierra. “I went from student to staff. That blew my mind,” she says. “I was like, wow, I really made it back.”

Learn more about getting your merch from Turn2U Productions

Teaching From A Life Of Experience

As the Academic Success Manager, Sierra now leads the team that supports justice-impacted students as they navigate The Last Mile’s web development curriculum.

When she first joined the team, her role focused on help desk support, project grading, and encouraging students through setbacks—an experience that continues to shape how she leads today.

Sierra’s role goes far beyond technical guidance, often helping them with the psychological strain of incarceration and imposter syndrome. “I talk to students about their confidence,” she says. “Because I know what it feels like to want to give up.”

Sierra brings something to the classroom that no textbook can teach—experience. “I don’t hide where I come from,” she says. “I let students know, I’ve been where you are. I’ve felt what you feel.”

That connection makes a difference. “They listen to me because they know I understand,” she says. “And when they start believing in themselves, that’s the best part of my job.”

Her presence in the classroom shows what reentry success looks like. She’s a living example of how employment for justice-impacted individuals leads to real transformation, both personally and professionally.

“The work I do now—this is my passion,” she says. “This is my way of giving back.”

Breaking the Cycle of Incarceration for Others

Sierra isn’t stopping here. She’s currently planning to pursue degrees in computer science and education—and she has Stanford in her sights.

Her dream is even bigger than personal advancement. She wants to open a community center that offers career and life skills to at-risk youth. “It would have trades like plumbing, mechanics, cooking, coding,” she explains. “But also mental health services and a safe place to just exist.”

She envisions a space where young people can find the tools—and the role models—to escape cycles of poverty and incarceration. “I want to be the person I needed when I was younger,” she says.

For Sierra Robinson, The Last Mile was a pathway to break the cycle of incarceration and to build a better future for people who share her lived experience.

“According to the expectations of society, I’m not supposed to be here,” she says, “But I am. And now, I’m bringing others with me.”

---

By Robert Roche, VP of Marketing at The Last Mile.

Want articles like this one in your inbox? Subscribe to The Last Mile Marker. This is a biweekly newsletter offering in-depth insights, critical updates, and inspiring stories on criminal justice reform and second chances.