Horrific Childhood, prison, helping others, college graduate - Jessica Henry

Okay Nightmare Success lifters, we are back, and man am I excited about this guest. Jessica Henry and I had to do this conversation twice because our first recording had tech issues, but I’m glad we did. Her story is one of those that just stays with you.

Jessica is a manager at Nation Outside now, working with reentry programs in Michigan. She graduated last spring from Spring Arbor University with her bachelor’s in social work, focusing on corrections counseling, plus a double minor in psychology and business. The thing that really gets me though? She earned three associate degrees from Jackson College while she was incarcerated. With honors.

Growing Up in Detroit’s West Side

Jessica’s story starts rough. Her mom was 18 with three daughters already when Jessica was born. They grew up on Detroit’s west side, and things changed when her parents divorced when she was five.

“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,” Jessica told me. “I always think what would my life have been like if I would have went in the house so that was like my first turning point looking back.”

The abuse at home was something they didn’t talk about outside the family. Jessica and her sisters weren’t allowed to wear shorts or skirts, always had to wear long pants. Looking back, she realizes everyone probably knew something was wrong, but as a kid, you think you’re hiding it.

Foster Care and Separation

By age eight or nine, Jessica was running away from the abuse. When authorities caught on to why they were running, the three sisters got placed in foster care. They were split up and sent to different homes across the Flint area.

“On the way there I kept trying to memorize the path and remember a tree or a sign 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.

Jessica spent two and a half years in three different foster homes. The first was with a couple in their 60s in a tiny village of 400 people. Talk about culture shock for a kid from the hood. She’d sit by the ditch with her Walkman listening to 90s music and reading library books.

The monthly visits with her sisters were in sterile rooms with just a couch and board games. No real conversation about what was happening to them or when they’d be together again.

Back to the Streets

At 13, Jessica returned to live with her mom, but that didn’t last long. After her mom had a nervous breakdown, their dad came up from Florida and got custody. Jessica was pregnant by 15, living the cycle she’d grown up seeing.

Her dad was what she calls “the dope man” and always had been. When Jessica needed money at 20, she got into cashing fraudulent payroll checks. That led to 19 charges and her first taste of jail when the Michigan State Trooper Fugitive Department showed up at 6 AM.

Her daughter, who was four or five at the time, opened the door for the cops. Jessica had tried to prepare her, telling her that when adults are bad, they go to the big house to get grounded.

Eight Times in Jail

Jessica ended up going to jail eight times total for various violations related to those original charges. She got her prison number during this time, even though she hadn’t been to prison yet. The number was 478775, and she still remembers it.

Her dad died of a heart attack in 2011, and Jessica tells this incredible story about his last words to her. She was holding his hand as they wheeled him to the ambulance, feeling his life leaving, and she said, “Dad please just say one word to me I promise you I’ll be quiet.” He said, “Just shut up.” Those were his last words to her.

The Final Arrest and Prison

In 2014, Jessica got arrested for armed robbery after being at a casino on Sweetest Day. She didn’t do it, but she wasn’t living right either. When the cops showed her a picture from the casino surveillance, she actually identified herself.

“They showed me the picture I said yeah that’s me like I snitched myself out,” she laughed. “I would look at that like you idiot but I didn’t do anything.”

After seven months in Wayne County jail, fighting a case she knew she’d probably lose, her daughter visited and told her to take a plea so her time would count. The judge gave her five years for unarmed robbery.

Finding Sobriety Behind Bars

While in county jail, Jessica opened her Bible for what felt like the thousandth time, looking for help. She found Matthew 13:45-46, about finding a great pearl and selling everything to get it. For Jessica, that pearl was her sobriety.

“I wrote it down on a little post-it note from my law pack and taped it with some shampoo tape,” she said. “I read it every day.”

She didn’t get sober right then, but she cut off all unhealthy relationships. On May 15, 2015, the day she got to prison, she got sober. She’s been clean for over eight years now.

Education Changes Everything

In prison, Jessica threw herself into education. She got her GED first, then started working on associate degrees. Having someone believe in her worth and see her potential made all the difference.

“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,” Jessica said. “I still had the same skill from what I used to do but now I’m using them for good for my education.”

Full Circle

Today, Jessica uses everything she went through to help others in reentry. She starts most conversations by saying she spent nine years of her life incarcerated total, because that shared experience is what builds trust.

Her daughter is 24 now, doing amazing. She has her own apartment, a job, a three-year-old daughter, and her life together in ways Jessica never had at that age.

Jessica’s working with six or seven interns right now, teaching them skills for reentry. When I talked with her, she was always looking for funding and resources. The difference between her help and others? She’s been exactly where her clients are. That matters more than any degree or training manual ever could.