Water glasses gently chime over white table clothes as author, educator and journalist Mitchell Jackson, 38, talks about being incarcerated and how some dudes he knows who, with little else to hang on to except the most rudimentary forms of respect, will kill you for stepping on their sneakers.

“I know people who would rather die than be disrespected,” Jackson says.

Just a few months ago, Jackson was back in that world at a house party in Portland, Ore., feeling the push-pull of the old life that informed so much of his new novel The Residue Years, and his present reality as an acclaimed writer and teacher living in Brooklyn.

“I didn’t even know that I was attending a gang-member party until I got inside and I noticed that everyone around had on red and they were all saying, ‘Bloods,’” Jackson recalls. “I could have left. But I started seeing people that I knew. I felt a certain comfort. The smart guy inside of me said, ‘Get out of here.’ But the other guy inside me said, ‘But these are people you know, and this is your scene. This is the life that you know. So, you don’t have to leave. You should feel comfortable here.’ I guess I’m always struggling with how far to go on either side.”

Although he ultimately fell prey to the culture of drugs and despair for a time, Jackson says he never really fully committed to the lifestyle—and that made all the difference in the world.

“I had a friend and he said that the first time he ever went out to sell drugs, he saw a guy get shot and killed,” Jackson recalls. “At that moment, my friend said he had to decide whether he was going to be in this life, or this was going to scare him off and he was going to do something else. He decided then, ‘I’m in this full time.’ I think for a guy that says that, it’s really hard to divorce yourself from that mentality. I was always half-in. I never committed to it. I was either half-playing basketball or half-hustling. But I was never fully on either side. And I think that allowed me to pull away from it when I needed to pull away from it.”

Jackson, whose prior work includes Oversoul: Stories and Essays, started much of his writing behind bars. But not necessarily because he was suddenly overcome with some kind of insistent muse. 

“I didn’t grow up saying, ‘I want to be a writer,’” Jackson says. “I didn’t grow up saying, ‘I’m going to write a novel.’ And even when I had 100 loose-leaf pages, it still didn’t equate to me that it was going to be in book form one day.”

Since dedicating himself to the writing life, Jackson has earned an M.A. in writing from Portland State University and an MFA in Creative Writing from New York University, where he also teaches and edits “Dossier Journal.” He also garnered fellowships from The Center for Fiction and Urban Artist Initiative.

To shoot the equally provocative documentary that accompanies The Residue Years, Jackson sat down and talked with the very judge who years ago sentenced him to prison.

“We sat in his courtroom,” Jackson says. “I sat on the witness stand. He sat up on his...I don’t know what you call it...to me, it’s his throne. And so, we talked. He didn’t necessarily remember my case, but he remembered all the drug cases that he had that were like mine. It was interesting to see his vantage point.”

What’s not as clear, however, is to what, if any extent, the sentencing judge appreciated Jackson’s reality growing up.

“People don’t have options,” Jackson says. “If you do five, seven, eight or nine years, and you come home, what are you going to do? You can’t get your record expunged. No one wants to hire you. And then you have this legacy of once having money. So when you come home, everyone is judging you by what you make, the kind of car you drive. In a small city where everyone knows what you did, I think you feel compelled to keep up that standard.” 

But Jackson’s journey didn’t stop at the judge; he went all the way back to prison—this time in an effort to help others get out of the same trap that ensnared him and so many friends.

“I hope it resonated. I told them that ‘I’m no different from you guys. I know what it’s like be here and to have to go and get on your bunk for count time. I was in that same seat. I don’t feel like I’m better. I just made some different decisions”

And had he not had the experiences he had growing up, Jackson doesn’t think he would ever have become the writer he is today.

“If I had lived a charmed life, I would have been playing ball until I was 30 or something, and then got a job coaching somewhere,” Jackson says. “That really was the dream for people back home.”

Joe Maniscalco is a writer living in Brooklyn.