The Challenges of Reentry
- Spencer Shelton

- Jan 16
- 5 min read
I wish I could say that getting out of prison is the easy part.
That once you’re released, life is so much better.
That those hopes and wishes you had dreamt up during your incarceration become actualized. That life becomes normal again. That family, friends, and your neighborhood welcome you home with open arms.
But release from prison is not a new beginning or a second chance for many of the men, women, and teenagers we work with. Instead, it’s often just the continuation of a long, hard road.
Two of our horticulture students were recently released. Prior to their release, they both told me the same thing: “I’ll give you a call when I get home.” I’ve heard this same line many times and by this point, I know what to expect.
Their call won’t come for several weeks. You see, when released, a couple different things happen.
They spend days catching up with family and friends. Everyone is excited to see them again. They sleep long hours, making up for years of fitful sleep inside prison. They lose weight as they’re no longer surviving off a steady diet of processed foods. They enjoy their newfound freedom, sometimes partying, sometimes not. They spend hour after hour watching TV or scrolling on their phone because they haven’t had a device of their own for years. They are blissful and content – there’s no reason to call their former horticulture teacher. They don’t want to think about prison at all. I get it.
But gradually, things change. Family and friends have to go back to work. No one’s just sitting around and able to drive them anywhere they desire. Scrolling on the phone gets boring. They realize that “real life” must begin.
So, they go out looking for jobs. They’ve heard that the economy is doing well and it’s easy to find entry level jobs. They’ve heard that societal attitudes towards the formerly incarcerated have changed, that it’s easier than ever to get a job, that they don’t have to hide their past. Prison officials have told them that many companies no longer have a checkbox on job applications asking if they’re a convicted felon. They find this to be delightfully true and apply to job after job.
When their applications are accepted, they become elated. Getting a job wasn’t so hard after all. And then they’re told that the company must run a background check. Excitement turns to fear.
Hiring managers are at least kind enough to call back. “I’m so sorry, but we just can’t hire someone with a record.” “If it was up to me, we’d hire you today.”
Reality begins to set in. Reentry isn’t going to be as easy as they thought. They pick up odd jobs from friends, family, and neighbors – cutting grass, painting houses. The days are long and the work is hard. Paychecks are far from steady.
As the days go by, fewer friends and family visit. No one has a clue where you just came from, the violence and horrors you witnessed for years on end. Everyone’s going about their normal lives, totally oblivious to the fact that you walked out of a prison just a few short weeks ago. You start to feel like you don’t belong, like you’re some kind of outcast.
Some begin to self-medicate – drugs, alcohol, days of sleep. Others totally withdraw to their bedrooms. Despair sets in.
Finally, they may remember their former horticulture teacher or the ministry that reminded them they were loved. They google HeartBound Ministries and find our website with our contact info. I get an email asking to talk. I call them almost instantly.
The stories are the same – parole is difficult to navigate. Jobs are really hard to find. They feel discouraged. I rarely ever hear the happy story that I so desperately yearn for.
They were so sure that getting out of the prison would be the start of something new. Life isn’t playing out like they thought it would.
Randy called me right before Christmas. He’d been home for two months and still no job. He’d just applied to an entry level position at a poultry farm. He was probably going to have to shovel chicken poop all day.
He sounded depressed. I told him so. I heard a deep sigh on the other end of the line, then a pause.
I remembered a line I’d heard many a time from HeartBound’s own Fred Eason.
I reminded Randy of Fred’s words: “Your worst day as a free person is still better than your best day locked up.”
He laughed. “You’re right, Spence. I forgot that. Really, the only thing I miss about prison is your horticulture class and Chaplain John’s class.”
He was living with family out in the country. The jobs nearby were few and far between. I encouraged him to use ChatGPT to help him craft a new resume and search for entry level positions. He informed me that as part of his parole conditions, he can’t use ChatGPT or similar websites.
I promised to look into job options for him. I asked him how his parole was going. He didn’t have any money and couldn’t complete the $400 class he was required to take. Until he completed the court-mandated course, his job opportunities would be severely limited. It was imperative that he start working soon. I asked if he’d set up a bank account yet so that when he got hired he could get paid by direct deposit.
Randy answered me like I was dumb. “Duh. You taught us how to open a bank account. And the stuff about the savings account. Of course I did that.”
We continued our conversation. By the end of it, he sounded hopeful. He told me about the pond he was fishing in later that afternoon. In my mind’s eye, I could see Randy, fishing pole laid over his shoulder, bait in hand, walking down to the water’s edge. After I hung up our call, I prayed for him. I knew he’d be just fine.
I met another recently released student for lunch the other day. As soon as we sat down, he apologized for not calling me earlier like he had promised before he left prison.
His story was similar to Randy’s. Setback after setback. But he had turned a corner. He was hopeful.
I asked what had changed.
“I started going to therapy. I’m processing all that happened to me. Those Saturday mornings therapy sessions are the highlight of my week.”
Taveuan Williams, a prisoner in Colorado, writes,
“When watered, the human spirit will bloom even in concrete. This isn't just about prison reform. It's about redefining justice. Retribution has its limits. You can't punish a man into wholeness. But you can love him there. You can show him a mirror that reflects not who he was but who he could become.”
Loving into wholeness. Watering the human spirit. Showing men and women and teenagers who they can become. That’s what we try and do.
Thank you for supporting that mission. Have a blessed week.
Spencer



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