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NEVER EAT THE CANDY ON YOUR PILLOW: THE REENTRY EFFECT  
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Derek R. Trumbo, Sr.
September 2, 2025
Prism
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_ Once out of prison, it felt like the world was shifting beneath my
feet, and even the weather conspired to keep me off balance _

, Credit: Designed by Rikki Li

 

_Dear Reader,_

_I’m sorry to leave you hanging __after my last cliffhanger of a
column_
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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
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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_
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_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._
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_Through in-depth and thought-provoking journalism, __Prism_
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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_.
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* Prisons
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* Prisoners
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* Reentry
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* criminal justice system
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