Columbus Sanders has spent more than three decades in Missouri prisons. During that time, he’s been a productive member of the state’s incarcerated population, holding kitchen, factory and janitorial jobs. 

Most recently, Sanders, 73, has worked as a hospice porter, where he keeps dying people company.

Despite his work success behind bars, Sanders is unsure how he’ll make money when he leaves Northeast Correctional Center in Bowling Green, Mo., which rests near the border with Illinois. 

“Honestly, I don’t know. I have never had a legitimate job” on the outside, Sanders told me during an interview at our prison.

After a moment, Sanders reconsidered and said that he could “maybe be a mentor to the kids out there, to help put them on a better path.” 

Landing a job will be only one of many challenges that Sanders will face when he leaves prison in four years. Those barriers to reentry underscore an important fact that any incarcerated person faces if they are lucky enough to leave: Regaining freedom is exciting, but reentering the outside world can be frightening too.

Recidivism statistics for the U.S. and my state confirm those feelings. One report, from the Most Policy Initiative, found that about 50% of people who left Missouri prisons between 2012 and 2016 returned within five years.

As people leave prison, they face challenges not only with finding employment but also many other basic necessities. Depending on the severity of the charge that sent you to prison, you might be ineligible for social services such as student loans or public housing — not to mention that many states bar people with felonies from voting. 

That leaves people who are reentering the outside world with barriers to housing, employment and education — and, often, good and affordable health care too. 

Sanders was first incarcerated at the old Missouri State Penitentiary, once dubbed “the bloodiest 47 acres in America” by Time magazine. He survived his stay there, and is approaching the finish line to freedom. But leaving the familiarity of prison for the inevitable confusion and concerns of reentry is scary.  

“In here, I know everyone and everyone knows me,” Sanders said. “Out in the world I would be nobody, just another ex-con.” 

Wyman Brown, 53, feels similarly. Like Sanders, Brown has also been incarcerated for more than 30 years. I interviewed him in the summer, months before his release in mid-September. 

“Prison is what I can handle,” Brown told me at the time. “It’s the unknown of a world that has become foreign to me that scares me. But I’d rather face a world of unknowns than spend another second incarcerated.”

Both men faced the daunting task of reentering a world that has changed in ways they cannot fathom. Brown said his biggest fear is “not being able to make it” on the outside and returning to prison. 

Brown has watched some of these changes take place on his clear, plastic, 13-inch TV. But that’s not the same as experiencing them firsthand.

“The internet, cellphones, no more pay phones, even money — people don’t use cash as much,” Brown said.

Sanders anticipates reentry will make him feel “like a fish out of water.” 

“Things have changed so much out there,” he said. “I’m not sure I would even know how to order a pizza anymore.” 

After he leaves prison, Brown plans to get a commercial driver’s license from a trucking school in south central Missouri. Upon graduation, Brown said he would have a job waiting for him. 

“It is the perfect job for an ex-con with no [kids or wife], and there is a high demand for truck drivers,” Brown said.

Brown said he’s worried his older age will get in the way of adapting to life on the outside. 

“My age bothers me for a couple reasons,” he said. “I don’t have any money saved up for retirement, and I worry if I will be able to be successful as a truck driver long-term [as I age into] my 60s.” 

Sanders is concerned about connecting with family. He has only spoken to his grandchildren over the phone because he did not want them to see him in prison.

“I worry about how long I will have to spend with my children and my grandchildren who I have not even met yet,” he said. 

Despite the uncertain future, both men said they were excited and determined to be successful. They believe good things await them. Brown, for one, said he was ready to be independent again.

Brown said freedom will allow him to make his own decisions. “Freedom to eat what I want, to go where I want, and to do what I want,” he said. “The freedom to not be told when to go to bed or when to shower.”

Sanders wants to experience baseball and football games for the first time. And he wants to take his grandkids to Disney World for ice skating. But even the smaller moments of freedom will be meaningful. 

Right after he returns home, he’d like to go fishing again.

“I want to catch a great big catfish,” he said, “and fry him up, with some hush puppies.”