From Prison Inmate to Business Owner: Melissa’s Journey of Transformation

Nov 4, 2025

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How community, grace, and second chances change everything

Ten years ago, if you had told Melissa she would own a thriving business in downtown Billings, she would have laughed. At 37, she was caught in a cycle that seemed impossible to break, full of addiction, incarceration, and broken relationships that stretched back over two decades.

“I’m the oldest of six kids, and we come from a big family, but we weren’t very close to each other,” Melissa reflects. “I started using drugs at an early age, around 14. I’ve always done whatever I wanted, whenever I wanted, however I wanted, and nobody was going to tell me any different. I’ve had a lot of hard lessons in life that I had to learn the hard way.”

The Cycle That Seemed Unbreakable

By the time Melissa reached her late thirties, her life had become defined by the revolving door of the justice system. “I got done with probation and parole in 2018, and I have not reoffended,” she says. “But before then, I had not had a period in my adult life where I was not on probation and parole. I think I went two weeks before I was back in jail.”

The statistics weren’t in her favor. Most people in her situation don’t break free from these cycles. Her family had lost trust in her ability to change. “I had lost a lot of respect from my family,” she admits.

But in 2015, after treatment at Rimrock, Melissa found herself at CLDI’s Hannah House, and everything began to change.

Learning Community at Hannah House

When Melissa first arrived at Hannah House in November 2015, she was resistant to the most basic elements of community life. “I’ve always been really used to doing things on my own,” she explains. “At the Hannah House, they always had dinner together and they had family meetings, and that was really uncomfortable for me. It’s just not something that I was used to doing.”

The structured community life felt foreign to someone who had grown up in a family where “everybody came and went as they pleased.” But the Hannah House staff didn’t give up on her.

“I was really defiant. I just wasn’t good at hanging out with the girls. I always thought somebody wanted something from me, like they were trying to trap me,” Melissa remembers. “But it took some time and some real work.”

One of her most vivid memories from Hannah House involves a mouse problem that got the entire house involved in finding a solution. “I couldn’t sleep because I could hear this mouse chewing on the furniture,” she laughs. “I was up for days trying to catch this mouse. We got the whole house involved, and it just got a lot more fun when I finally let my walls come down and would actively participate.”

Caring for Grandmother

After graduating from Hannah House, Melissa faced a choice that would define her future. Her parents asked her to help care for her grandmother, who was in home hospice in Bozeman. “My brothers and sisters all thought that I was going to run away, that I was not going to stick it out,” she recalls.

But Melissa surprised everyone, including herself. For 18 months, she provided round-the-clock care for her grandmother. “She was supposed to only live a couple months, but she ended up living 18 months because life is so much better when people can be at home.”

The experience was transformative. “A week before she passed, she told the hospice nurses, ‘Melissa is my best friend.’ I never really had a relationship like that with anybody – somebody that actually trusted me and relied on me like that.”

The impact on her family was profound. “My brother, which is kind of a big deal, told me that I gained his respect back,” Melissa says. “When people lose respect, they don’t usually get it back.”

Rebuilding Relationships and Securing Stability

With her family relationships restored, Melissa focused on the most important goal: getting full custody of her son, who had been living with his father’s family. “I decided I wasn’t going to work jobs at night anymore. I was only going to work during the day so I could be present in every area of his life. That meant taking a job that was $10 an hour, and that was a struggle.”

That $10-an-hour job was at the Mail Drop, where she worked for Lynn, who had owned the business for 45 years. “I was not a very good employee when I started there,” Melissa admits. “I was late more times than I can count, but he always just was very kind and gracious with me.”

When Melissa’s sister passed away, Lynn demonstrated extraordinary grace. “He just let me take all the time that I needed. After some time off, he came to me and said, ‘Do you want to come back to work? Because customers really like you.’ But he said, ‘I really need you to be on time.'”

Melissa made a commitment that changed everything: “I said, ‘I can’t promise you because I don’t know, but I will do my very best.’ And I was never late again.”

From Employee to Owner

What started as a joke became reality when Lynn decided to sell the Mail Drop. “I told the other employees, ‘He’s selling the store, he better not. He better sell it to me,'” Melissa laughs. “So it was just like a joke. And then I told him, ‘Well, if you’re really going to sell it, I’m really going to buy it.'”

Despite having no credit history and never having taken out a loan, Melissa found a way to make it happen with her mother’s help. On June 30, 2024, she became the owner of the Mail Drop.

“I never really thought about it until I made the joke, she reflects. “I never thought that I would be a business owner, especially with the criminal background that I’ve had.”

Paying It Forward

Today, Melissa’s transformation extends far beyond her personal success. She’s created a workplace culture built on the same grace she received. “My employees are also recovering addicts and single moms,” she explains. “I try to do that with my girls because we all have things that go on in our life.”

She’s intentional about serving her entire community: “We serve downtown Billings, and we have every type of person you can imagine come in there. I like to keep our prices lower so that we can still serve the underprivileged community because everybody deserves to have their stuff safe.”

The ripple effects of her transformation continue to spread. “I make sure that we take care of our drivers too. We have a refrigerator with some cold drinks,” she says. “I’m in a position where I can help, and now I get to sponsor community events. I always wanted to be that person that supported this, that, and the other, and now I get to.”

A Message of Hope

Today, Melissa’s story serves as a beacon of hope for others who might feel trapped in their circumstances. 

“I’m not embarrassed of my past because it’s just who I am, and it’s just what’s happened. It doesn’t mean that that’s happening today, but I wouldn’t be where I’m at today if I didn’t have that past.”

Her relationship with her son, now 18 and a high school senior, exemplifies the complete transformation of her life. “I have such a good relationship with him now. He tells me things, and he just cracks me up because he says, ‘Mom, there’s something I’d like to talk to you about.’ I never had that kind of relationship with my mom.”

For those supporting organizations like CLDI, Melissa’s message is clear: “I had a lot of help from a lot of people, undeservingly, I think. Sometimes you just need a little bit of hope.”

Her journey from Hannah House to business owner proves that with the right support, community, and opportunities, transformation is not just possible – it’s powerful enough to change families, communities, and futures for generations to come.


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