Horrific Childhood, prison, helping others, college graduate - Jessica Henry
Jessica Henry shares a first-hand addiction story and practical lessons for people navigating legal pressure, incarceration, or reentry.
Key Takeaways
- Jessica earned three associate degrees with high honors while incarcerated and graduated with a bachelor's degree after release.
- She got sober on May 15, 2015, the day she went to prison for the final time and has maintained sobriety for over eight years.
- Jessica now leads reentry programs at Nation Outside, using her lived experience to help others navigate the challenges of coming home from prison.
When I talked with Jessica Henry about her journey from a horrific childhood to earning a bachelor’s degree, she told me something that stopped me in my tracks. “Everything I’m doing is something I love,” she said. “I had been through so many things in my life, juvenile delinquency, foster care, teen pregnancy, addiction, rehab, therapy, prison, jail, probation, parole, and I’m like, why did I go through all this? And now I know why. It’s because I can help those who are struggling on going through similar things to make changes one step at a time.”
Jessica spent nine years incarcerated across multiple sentences. Today she’s a manager at Nation Outside, mentoring people through recovery and reentry. She just graduated from Spring Arbor University with her bachelor’s in social work, focusing on correction counseling, plus a double minor in psychology and business. She also earned three associate degrees with high honors while incarcerated at Jackson College.
But getting to this point meant surviving a childhood that would break most people.
Growing Up in Crisis
Jessica’s story starts on the west side of Detroit. Her mom had three daughters before turning 18. When Jessica was five, her parents divorced, and she remembers it as a turning point. “They had my little sister play in tug of war, one had her arms, one had her legs and my mom’s like getting the van and my dad’s like getting the house and I went the van with my mom and I always think what would my life have been like if I would have went in the house.”
The abuse at home was physical, psychological, and verbal. The girls weren’t allowed to wear shorts or skirts, always forced to wear long pants to hide the evidence. “We didn’t take it outside of the home you know maybe it was a fear of being judged or a fear of being taken away from our home,” Jessica told me. “But you know I would go to my friends my friends knew you know the abuse that was going on in my home but their parents didn’t know.”
By age eight or nine, Jessica was running away. Not for adventure. To escape. When authorities caught on to why the girls kept running, they were placed in foster care. Jessica was ten years old.
Split Up and Searching for Home
The three sisters got separated into different foster homes across the Flint area. Jessica ended up in three different placements over two and a half years. “On the way there I kept trying to memorize the path and remember a tree or a sign you know so I could make my way back home because even if those things were going on that’s where I wanted to be with my family with my mom in my home,” she said.
The monthly family visits happened in a sterile room with a couch and some board games. “It was just like what’s the word like sterile,” Jessica remembered. “There wasn’t love that we didn’t talk about the things we should have talked about like mom why did this happen to us right you know or mom when it you know we of course we said mom was going to get us back.”
After her mom had a nervous breakdown and another incident involving Jessica’s older sister, their dad came up from Florida and gained full custody. Jessica was 13 when they moved in with him. There were no rules or structure this time. She got pregnant at 15.
The Criminal Path Opens
After leaving her daughter’s father at 20, Jessica moved back with her dad, who was still dealing drugs. She started selling too. When rent was due and drug money wasn’t enough, a neighbor suggested fraudulent payroll checks. Jessica opened a bank account in her real name and cashed checks at nineteen different banks across three counties.
Eight months later, the Michigan State Trooper Fugitive Department showed up at 6 AM. Jessica’s five-year-old daughter opened the door. “I thought Jill was the police here to take my mama,” the little girl said. Jessica had prepared her by explaining that when adults are bad, they go to the big house to get grounded.
That first taste of jail at Genesee County was nothing like Jessica expected. The smell hit her first. “Smashed up baloney and body sweat,” she describes it. “I have been in there once since my incarceration on a good note and it still smells like that.”
Finding the Pearl
Jessica went to jail eight times on those original charges, violating probation repeatedly. In 2011, her dad died of a heart attack. His last words to her as she held his hand in the ambulance: “Just shut up.” Jessica was holding the house together for her 13-year-old daughter when she got arrested on an absconding warrant in February 2012 and went to prison for the first time.
She got out, enrolled in college, got her daughter back. But she needed money and went back to selling pills. In October 2014, she was arrested for armed robbery after being at a casino where a crime occurred. She didn’t do it, but she wasn’t living right either. After seven months in Wayne County jail, her daughter told her to take a plea so her time would count. Jessica got five years for unarmed robbery.
“The day I wrote out the prison May 15th 2015 is the day I got sober and I’ve been sober since then it’s like eight years and four months I’ve been sober,” she told me. In jail, she’d found a Bible verse that hit different this time: Matthew 13:45-46, about finding a great pearl and selling everything to get it. “For me that pearl was my sobriety and I knew I needed it I knew that was getting in my way.”
Education as Liberation
In prison, Jessica threw herself into education. She got her GED on her first bit, then earned three associate degrees with high honors at Jackson College while incarcerated. “Somebody took the time to see value in me and I felt so worthy that I could get my education and start a new path. I still had the same skill from what I used to do but now I’m using them for good for my education.”
Music got her through the hard days. She’d use her JPay player to download songs and write emails to family. On the difficult moments, she’d remind herself that emotions wouldn’t kill her, but they could strengthen her.
Helping Others Navigate the System
Now Jessica works at Nation Outside, mentoring people through recovery and reentry. Her approach is direct. “That’s one thing that I usually do. You’ve got to know your audience, but I usually start off with, hello, my name is Jessica. I’ve spent nine years total of my life incarcerated because that lived experience is key, especially somebody coming home who may have issues with authority or somebody who hasn’t been where they’ve been.”
She’s working with six or seven interns, teaching them skills for reentry. She’s always looking for funding and resources. The difference between her and other service providers? She’s walked the walk.
“If you’re coming home and you have it in your heart to want to help others, that’s the thing that it is that shared lived experience that’s going to help somebody maybe take the next step that they were leery to take before because of authority issues,” Jessica explained.
Her daughter, now 24, has her own apartment, a legitimate job, and a three-year-old daughter. “My daughter’s doing so much better than you know I ever was at her age,” Jessica said.
Jessica’s collecting degrees and helping others do the same. She knows why she went through everything now. Every nightmare led to this moment where she can grab someone else’s hand and show them the way forward. One step at a time.


