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There are people in our community who have surrendered to prison with a comprehensive plan. They put it on paper, thought it through, walked in ready to go. And on day one, the case manager dismissed it. “I didn’t ask for this. I don’t have time to read it. I know what’s best for you.”

Some case managers don’t care. Others are testing you. They want to see if you’ll fold at the first pushback, if you’ll quit, or if you’ll stick with what you built.

Earlier this year in Tampa, I filmed a video about a physician who had the opposite experience. His case manager called him in out of the blue and said, “I’m going to give you ten months in the community.” He had only expected a few. He didn’t ask for it. He wasn’t lobbying. He just lived in a steady, healthy routine. He figured nobody was paying attention. He was wrong. They were watching. They always are.

And it isn’t just case managers. The people you associate with matter just as much. On my first night in prison, a man named Arthur approached me. He told me this could be a productive experience. He got me running, got me thinking about diet. He looked like me—middle-aged, white, law school background, supportive family. It made sense that I gravitated toward him.

Then the cracks started. He mocked a man with a neck tattoo that read “too blessed to be stressed.” He laughed at another prisoner who had lined up a fast-food job for reentry. Many of us congratulated him. Arthur said, “I’d rather stay in prison than work in fast food.” At first, I ignored it. I rationalized that nobody was perfect, that Arthur had helped me, that it wasn’t my place to say anything. But I felt like a hypocrite. I was blogging daily about accountability and not enabling, yet I was enabling Arthur by staying silent.

The smaller moments stuck with me more than any big confrontation. Walking to chow and hearing him sneer. Walking the track with a man who had white-supremacy tattoos. He explained he had taken them on in state prison for survival, not belief. Arthur mocked me later for talking with him, calling him “white trash.” That was the final push.

I ended the friendship. I told him directly: this doesn’t align with my values, I don’t feel comfortable with it, I wish you well. And I felt free. I spent more time with Michael and others who were building, who showed gratitude instead of contempt. I found myself among people who didn’t look like me, didn’t talk like me, but who were generous and authentic. The man with the neck tattoo was one of the most helpful in the dorm.

That choice gave me space to contribute. Someone suggested I teach a finance class. For 30 days, I explained the basics—stocks, dividends, why saving $50 or $100 a month matters. I got more satisfaction out of that than any lap around the track. And the men appreciated it. I should have documented that class more deliberately, because that record would have mattered later.

If you’re going in, remember two things. First, case managers may dismiss your plan on day one just to see how you’ll respond. Don’t fold. Keep building. Second, the people you associate with will either reinforce your values or corrode them. Choose wisely, and document what you contribute. That record may be the difference between more prison time or more liberty.

Justin Paperny