Illustration by Liza Burns

Writer’s Block

An award-winning writer struggles to explain himself to the parole board

By James

I entered the criminal justice system 8,643 days ago. I was 17 years old. My crime shocked many, including myself. I was sentenced to 25 years to life in the penitentiary.

Now, at 41, I am 15 months from appearing before the Board of Parole for the first time. There I will face a panel of three who know me only by an inch-thick institution file. I will need to explain what I did and why I did it and who I am.

I am terrified.

I’ve heard from other prisoners that the parole board puts more focus on the crime committed than the growth and insight gained in the many years after conviction. I will have to relive that moment. I will have to articulate it in a way that shows that I am no longer that boy prone to outbursts of violence. I am a man who has spent more than two decades struggling with shame for what brought me here. My future depends on how I explain it.

I must write a parole packet that includes all the minute details of my crime, the programming I’ve participated in and an overview of why I should be paroled — something that I inherently understand isn’t deserved. 

I have become an award-winning writer while incarcerated, but I’m finding it extremely difficult trying to write this document for the board. I worry that my words, real and heartfelt to me, will be interpreted as cheap and meaningless when considering the permanence of the harm I caused as a teen. 

My family and friends tell me to trust. They tell me to listen to my heart and just write. So I do.

I’m writing about the shame I feel. I’m writing about accountability and remorse, and how I’ve grown to completely understand the importance of my choices. Even the small choices. Especially the small choices.

Sitting inside my cell, I write draft after draft by hand. My garbage can often piles up and spills over with wadded up paper, all these versions which fail to tell the story of who I am. I strive for complete transparency. I want to write with my chest torn wide open. I owe the truth. Nothing but.

I’ve been working on this document for seven years, and I’ll keep working on it for 15 more months. It’s not just my lifeline; it’s my understanding of myself today and how I got to where I am.

My peers, many who’ve seen the Board of Parole themselves, often tell me that I will do fine. They say that I will likely be given a second chance by a board who will recognize the hard work I’ve done. They tell me that my long resume of clear conduct, educational achievement, leadership opportunities and programming speaks for itself.

At times I feel hope. But I also feel its absence amidst the humble understanding that continued incarceration is not unmerited for the crime I committed. Some things can’t be erased or rewritten.

James is a member of Lauren Kessler’s Lifers’ Writing Group at Oregon State Penitentiary. This year his story, “Another One Bites the Dust,” earned an honorable mention from the Pen America Prison Writing Contest. In 2018, his story “Sophia” ( placed first in the memoir category.

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