Our Guest: Jessica Hicklin’s Journey from Darkness to Advocacy

The 16-Year-Old Making Life-or-Death Choices

Jessica Hicklin was a 16-year-old kid trying to save her mom from jail when everything went wrong. Her mom had written $2,400 worth of bad checks to a casino and was facing charges. Jessica tried to get a loan, tried to access her college fund, but nothing worked. So she turned to what she knew: drugs. What started as a plan to help her mom became a nightmare that would define the next 26 years of her life.

“Over the course of probably four days it went from, I’m going to save my mom to, I am going to save my own life,” Jessica told me when we talked. “There are police reports that show where I told friends that like I think the guy was supposed to be doing the deal that’s going to try and kill me.”

That guy was Sean, her best friend at the time. The person she trusted most. When the drug deal went bad and he tried to rob her at gunpoint, Jessica took his life. A week later, she was arrested and certified to stand trial as an adult. At 17, she was sentenced to life in prison without parole.

Growing Up in Chaos

The path to that moment had been building for years. Jessica grew up in what she calls “generational abuse”, a broken home with a physically and emotionally abusive father and stepmother, and a mother who didn’t have the tools to protect her kids because she came from the same background.

“You know, as kids that go through that type of abuse, there’s two phases,” Jessica explained. “There’s the one where you all band together to try and save and protect each other. My brother got a lot of physical abuse because he would try and take the beatings for his siblings and my sister would be there similarly. So we all kind of took our turns trying to defend the others.”

By age nine or ten, Jessica was looking for an escape. She found it in drugs and alcohol, watching her family use substances to cope with their problems. The family even tried to get help through family services, but Jessica’s father was on the family services board. They referred the case right back to him.

“When you scream loud enough and nobody cares, then you go inwards,” she said.

The Unlikely Scholar

What makes Jessica’s story even more complex is that she was brilliant. While her home life was falling apart, she excelled in school. She was accepted to college at 16, inspired by watching Doogie Howser and wanting that kind of life.

“I was, from the time I was young, I grew up watching Dookie Hauser, for those of us that are old, not but never Dookie Hauser. And that’s where I wanted to be,” she told me. “That was my, and I dedicated myself to doing that. I just wanted to live the right life a good life. And I just couldn’t.”

School was her refuge, the only place she felt safe. When a principal was ready to throw her out for attendance problems, a guidance counselor stepped in. Jessica had scored a 28 on the ACT as a freshman. Something didn’t add up, and that counselor helped save her academic future, at least temporarily.

Walking Into Maximum Security

When Jessica entered Potosi Correctional Center in Missouri, she was still a teenager facing the rest of her life behind bars. This wasn’t just any prison, it was a maximum security facility that housed death row inmates in general population.

Her orientation was brutal. “My R&O was, I tell people, my R&O was basically three sentences. A lot of time, you’re going to die here for what to do with your life. There’s the door,” she said.

They classified her as a “high alpha”, a predatory inmate, and threw her in with the most dangerous prisoners. There were no security cameras, many guards were corrupt, and it was one of the most violent prisons in Missouri.

Jessica was assaulted three times in her first two years. The fourth time someone tried to attack her, she fought back and ended up in solitary confinement for nine months. Those first few years, she admits, she was “not a nice person.”

The Transformation

Everything changed during that nine-month stretch in solitary. A tiny nun named Sister Elaine would come by every two weeks and talk to Jessica through the slot in her door. At first, Jessica was frustrated and angry. Who was this woman? Why did she care?

But Sister Elaine became the image of the person Jessica wanted to become. “If I was going to spend the rest of life, my president doesn’t mean I was dead and doesn’t mean that I couldn’t become a good person,” she realized.

Jessica became a Buddhist, took vows seriously, and began retraining her brain. A spiritual advisor later told her something that stuck: in any moment, you have two choices, to increase happiness in the world or decrease it.

“You can’t change your life if you can’t change your mind,” Jessica said.

Building Something from Nothing

From that foundation, Jessica built an extraordinary prison career. She became a paralegal for death row inmates, helping people who were within 30 days of execution with their legal research. She taught GED math classes. She got involved in hospice care.

When the state cut education funding for maximum security prisons, Jessica saw an opportunity. She taught herself computer programming from a stack of books as tall as a fifth-grader, eventually co-founding Unlocked Labs, an organization that helps incarcerated people continue their education and find better jobs when they’re released.

After 26 years, Jessica walked out of prison in 2022 as the first transgender inmate in Missouri to successfully sue for the right to access hormones. The deputy warden called her a “superstar” for her ability to change the system from the inside.

Today, Jessica continues to wake up each morning asking the same question that guided her transformation in prison: “What is the best thing I can do today to reduce suffering in the world?” Sometimes the answer is building technology to help formerly incarcerated people. Sometimes it’s something else entirely. But the principle remains the same, choosing to increase happiness rather than decrease it, one moment at a time.