Dear Reader,
I’m sorry to leave you hanging after my last cliffhanger of a column. The days have flown by since I was released from prison on April 1. That’s right, my date with the parole board actually went better than I expected. I’m now a free man.
Immediately upon leaving prison, I was bombarded with overwhelming headlines about the millions of people under flood watches, the Department of Homeland Security’s many efforts to remove immigrants seeking a better life in America, and the threat of tariffs. In all of my daydreams about the day I would be set free, I never stopped to imagine the world I was walking into under the second Trump administration. In the few months I’ve been out of prison, my entire world view has shifted—and so, too, will this column.
I may be out of prison, but I’m still stuck in the criminal legal system. While I can no longer share stories about life inside, I can definitely tell you about the intricacies of life on parole.
This is the first of many columns that will examine reentry and the many unexpected changes to the outside world that prison doesn’t really equip people to navigate when they’ve spent decades behind bars. To you, some of the changes might seem minor, such as new technologies and different fashion. To me, it’s quite overwhelming to now have an abundance of choices after decades of restrictions on everything from food and books to clothing and movement.
In future columns, you’ll be right alongside me as I navigate parole, finances, relationships, housing, and what I already recognize as the unrelenting news cycle. This column will now serve as a glimpse into the many unpredictable challenges people experience when re-entering real life after years behind bars.
For now, I’d like to tell you about my first days spent outside of Kentucky’s Northpoint Training Center in almost 20 years.
Stepping onto the road that April morning, I was overwhelmed not just by the weight of freedom and the smell of fresh air beyond the fence line, but also by a world bursting with noise, color, and movement. The world outside the prison seemed to pulse with electricity: Digital billboards flickered above me, and every passerby appeared consumed by the glowing screen held in front of their faces. The cars zooming down the highway looked like something from a science fiction magazine I once skimmed in the prison library: silent, sleek, some powered by a different kind of energy. Even their headlights had changed: sharp and blue-white, instead of the mellow amber hue I remembered. My anxiety as I took in the new world around me was so palpable that my driver suggested taking a deep breath and remembering that outside wouldn’t always feel so overwhelming.
My eyes nearly bulged out of my head the first time I went to a grocery store; the price of food shocked my system. By my third day of freedom, I experienced a bit of a crisis in confidence, and I convinced myself that it will take me years to find my balance and figure out how to live a life beyond prison. But it wasn’t all bad. After many years locked up with men, I admit it was hard not to notice how short some women now wear their dresses, and how boldly they defied societal expectations around modesty.
At times I felt like I stumbled into a river that had grown wild and swift in my absence, and it took everything in me to keep my footing on slippery stones. This wasn’t prison, but I still felt confined.
People everywhere fascinated me. What really struck me was their pace. People moved fast, heads bent intently, earbuds tucked in, faces unreadable. At times I felt like I stumbled into a river that had grown wild and swift in my absence, and it took everything in me to keep my footing on slippery stones.
This wasn’t prison, but I still felt confined.
The simplest tasks—buying a coffee, crossing the street, asking for directions—suddenly felt like small tests of survival. I talked about this to a friend, who offered some common sense advice, such as instructing me to ask my phone for directions. Could my phone talk to me? Ordering at a café, I stared blankly at a tablet covered in mysterious icons, which I later learned were self-service options. There were also payment methods I’d never heard of, and I felt embarrassed to ask for help. Even the currency seems to have shifted, with people tapping phones or waving cards instead of counting bills. I pay with bills that now look like Monopoly money.
Each moment outside, the distance between the world I left behind in prison and my new reality felt more stark—and for all the joy of freedom, there was a persistent sense of being a stranger, to others and to myself.
But less than a week out of prison, I soon had the kind of problems that snap you out of fear and doubt.
On April 3, I woke up to a flood watch and severe storm alert. The apartment I lease sits less than 10 yards from the Kentucky River.
“Is the river going to flood?” I warily asked my landlord.
“It shouldn’t,” he said. “If it does, it’ll be no more than a few feet. We got about three feet in February. Ain’t had a major concern since 1978.”
His reassurance was casual, almost dismissive, as if the river’s unpredictability was no cause for concern—just one more current to navigate. I nodded, trying to hide my apprehension. Inside I felt nothing but doubt. The world had shifted beneath my feet in ways large and small, and now even the weather seemed to conspire to keep me off balance.
In the end, my landlord was wrong. Very wrong, in fact. Outside, the sky pressed down low and gray, river water swirling in shades of brown, swift and swollen. Sirens blared somewhere in the distance, another new sound, sharper and more frequent than I remembered. I found myself obsessively checking my phone for updates, marveling at how even natural threats now arrived as pixelated warnings, urgent and impersonal.
I sat on my gifted couch, watching rain pelt the window. Everything felt so fragile, as I tried to imagine what it would mean to lose my new refuge to the whims of nature. My mind wandered back to prison storms: the communal hush when thunder shook the cinderblock walls, the uneasy camaraderie amid shared uncertainty. Out here, the storm felt lonelier, the possibilities far more endless and uncontrollable.
In the early hours of April 6, the water had risen so severely that I had to be boated away from my fully submerged apartment. With less than a week of freedom under my belt, I lost every material possession to my name, all the items I promised myself in prison that I’d get when I was free. My clothes, my TV, my bed. I also lost drafts of novels and short stories I wrote while imprisoned, along with photos of friends and family I accumulated while inside.
Yet, I was still alive. Still free.
Amid the wreckage and debris of the flood, I was rescued by community members who looked at me and saw not a former convict, but a flood victim who needed help. They saw me as someone worthy of help.
In the weeks to come, I saw even more community support, including a hotel that offered discounted prices to flood victims, local churches that fed us and provided clothing, and volunteers who helped with cleanup. Even people I’d never met in person offered assistance, including editors at Prism, who launched an online fundraiser to help with my recovery and reentry. Never in my life had I ever felt so accepted. Nowhere did I encounter people seeking to judge me or cast aspersions on my past. Instead, I found people who genuinely came together for the sake of uplifting someone in need: me. I was utterly speechless.
Rather than wrap up this column as usual with words of wisdom, instead I just want to express my gratitude: Thank you to everyone who lent a hand, offered financial support, or just checked in on me. This certainly wasn’t the reentry I imagined, but the kindness of strangers has carried me through.
The Right to Write (R2W) project is an editorial initiative where Prism works with incarcerated writers to share their reporting and perspectives across our verticals and coverage areas. Learn more about R2W and how to pitch here.
Derek R. Trumbo, Sr., a multiple-time PEN Prison Writing Award winner, is an essayist, playwright, and author whose writing has been featured in "The Sentences That Create Us: Crafting A Writer's Life... More by Derek R. Trumbo, Sr.
Through in-depth and thought-provoking journalism, Prism reflects the lived experiences of people most impacted by injustice. As an independent and nonprofit newsroom led by journalists of color, we tell stories from the ground up: to disrupt harmful narratives, and to inform movements for justice. Our vision is collective liberation and justice for people and communities who are historically oppressed. Subscribe.
