Jackie Tress never imagined she’d end up behind a dumpster, strung out on heroin and meth, stealing to survive. She certainly never saw herself waking up in abandoned buildings, shivering through winter nights, or looking over her shoulder, running from the law. But addiction doesn’t negotiate. It takes everything. And for years, it had taken everything from her.

“I was completely lost,” Jackie recalls. “I didn’t care who I hurt, who I stole from, or what I had to do. I told myself I had camaraderie with other homeless people, but it was really cutthroat. At my lowest point, I accepted that I was probably going to die on the streets.”

But fate had other plans. After yet another arrest—her seventh or eighth, she had lost count—Jackie heard about The Other Side Academy (TOSA). It was a two-and-a-half-year program, nothing like the short-term rehabs or halfway houses that had failed so many she knew. TOSA wasn’t just about getting clean; it was about learning how to live a completely new life. For Jackie, that was the only kind of program that had a chance of working.

A Second Chance, the Hard Way

When Jackie stepped into TOSA, she had no idea what to expect. What she found was structure—unwavering, intense, and at times, brutally honest. There were no handouts, no shortcuts, and no coddling. Instead, there was work. Real work. Jobs with purpose, where every individual was expected to pull their weight.

At first, it was overwhelming. Jackie had spent years living moment to moment, her only goal being her next fix. Now, she was surrounded by people who had been exactly where she was, but had transformed their lives.

“I looked at these women who carried themselves with confidence, and I couldn’t believe they were once addicts like me,” Jackie says. “But then they told me their stories. And I realized, if they could do it, maybe I could too.”

Learning to Be Trustworthy

Jackie didn’t just learn how to work, she learned how to be accountable, responsible, and trustworthy. One moment in particular stands out in her mind: when one of TOSA’s leaders, Lola, trusted her to clean her home.

“There was her engagement ring sitting right there, the keys to her car,” Jackie remembers. “She trusted me. And because she trusted me, I wanted to be worthy of that trust.”

For someone who had spent years lying, stealing, and manipulating, that trust was everything. It was the first step toward rebuilding her sense of self.

Hitting Rock Bottom: A Blessing in Disguise

Before TOSA, Jackie had plenty of opportunities to change. People had offered her shelter, food, even money when she was flying a sign. But every time, she had found a way to use those resources to sustain her addiction.

“When people gave me a tent, I’d trade it for drugs. When they let me shower in their home, I’d go through their medicine cabinet,” she admits. “I didn’t need a softer landing—I needed to hit rock bottom.”

And she did. That final arrest saved her life. If she had been released back onto the streets, she knows she wouldn’t have survived much longer.

The Hardest Part: Facing the Truth

At TOSA, there were no excuses. The hardest lesson Jackie had to learn was that she had created her own reality. For years, she had blamed her circumstances, her childhood, her trauma. But at the Academy, there was no space for victimhood.

“It was hard to accept that I was the one responsible for my life,” she says. “But once I did, I realized that meant I had the power to change it.”

She learned that addiction wasn’t a disease she was doomed to battle forever—it was a choice. And every day at TOSA, she made the choice to be different.

A Future She Never Imagined

Jackie didn’t just graduate from TOSA; she stayed on for an extra year as a mentor, helping others find their way through the same process that saved her. Now, she’s a coach at The Other Side Village, helping people who are transitioning from homelessness to stability.

“I wake up some days and I can’t believe this is my life,” she says. “I get to see people come in broken, just like I was, and then I watch them change. I get to be part of that process. It’s incredible.”

She doesn’t plan on leaving anytime soon. Watching others transform is what keeps her going. She sees herself at The Other Side Village for years to come, paying forward the second chance she was given.

Breaking the Cycle

Jackie knows that many people see addicts as lost causes. But she also knows firsthand that real change is possible. She’s living proof.

“It’s not about throwing money at the problem. It’s not about making life on the streets more comfortable,” she says. “It’s about giving people a real opportunity to change, but making them work for it. That’s what TOSA does.”

Jackie’s story isn’t just one of survival. It’s one of transformation. And it’s a story that proves, no matter how lost someone may seem, there’s always hope.