White Collar Prison (The End)

By: John DiMenna

White-Collar Prison. An Essay By John DiMenna. Originally Published at Minutes Before Six. Reprinted With Permission.

A Different Kind of Hell.

You can survive prison, and you can recover from prison, but prison never leaves you. On certain days, it feels like afterlife; other days, like a typical workday, and most days a bad dream enduring the slow torture of meaningless, menial tasks. I lived among one hundred other inmates, more wilderness than community. There is nothing more solitary than living among the exiled.

Despite the conditions, I embraced a life of contemplation, renewal, and earnest self-reflection. I kept a daily log/journal, using those scribbling as the source material for this manuscript. One morning, I woke up early before the 5:00 am count, it was still dark, some early rustling of others headed to the bathroom. I’d awoke from a dream that I was back in my old life, sitting in my office confronted by dozens of people, my partners, investors, all standing, while I remained in my high-back leather chair in a dark suit that was too tight and uncomfortable, all demanding an apology. Behind them were my children and employees with a desperate expression, a plea for an explanation to undo everything, and somehow make everything okay. I tried to speak but nothing came out and the people grew angrier and shouted at me to say something. When I woke up, in the dark, it was the first time I was happy to be in prison. Behind walls where no one could confront me, part of a community who didn’t judge me.

I lay there until the count came through, the guards flashlight abruptly in my bunk, passing as usual like a flash from a camera. I was relieved that I didn’t have to answer. I realized that I didn’t have an answer that I had spent my whole life avoiding answers, that I had never apologized even though I was remorseful, understood what I had done that I had lied, been dishonest, and most of all dishonest with myself, and that I had spent my whole life running from confrontations and questions. I determined that my failure was a failure of character, something intrinsic, inherent and inevitable. Confrontation and Crisis are the tests of character. The confrontations and crisis came and I failed the tests every time. I concluded that men can always dream of a new start and redemption but can never extinguish the history of their malfeasance. Overcoming disgrace is a fools errand. I could only accept it and try and move forward.

I got dressed in the dark, as usual, my work uniform, a clownish outfit of black and white checkered pants, a white shirt and a wrinkled white cap with Kitchen Staff in black across the top. I embraced it, and strode resolutely to my post, the small corner of the kitchen where the dishwasher resides, began stacking the trays, inserting soap for the stainless-steel dish washing machine, prepared the counter for the inmates to deposit their trays, all done with something new that was not pride but was purposeful. The best I could do for an apology.

Gratefully, after only eighteen months, I received a reprieve due to the COVID-19 pandemic. I was subsequently released and confined to Home Incarceration for the remainder of my sentence. But returning home from prison, the relief fades sooner than you’d think. The old failures still reside there, and prison makes the trip home with you. No one’s the same as you remembered them. Friends are uncomfortable, distant, measuring and opportunities foreclosed. Ambivalence follows warm greetings. And then there are the questions asked and the more painful ones, not asked but implied in half measures and stares and pauses, more revealing, hurtful than a thousand insults. You try to put on a good face, show courage, and believe it yourself for a while. But it doesn’t last, resonate. You’re damaged goods because prison doesn’t prepare you. All the stuff on the bulletin boards, the courses, seminars: resume building, reentry strategies, interview preparedness, family orientation, all bullshit. Every inmate leaves with only a T-shirt, a new pair of jeans, a pair of sneakers, a felony conviction, maybe $100 from his prison store account and an excruciating self-loathing. The experience of incarceration, its agony, sense of exile, isolation and the misery of day-to-day confinement lingers long after the arrival home.

It’s been four years since my release. I’m still disconnected from humanity, but I think I know what makes life meaningful and worthwhile. I got that much out of prison. Not sure I didn’t know it before.

John DiMenna is a member of the Ministry’s White Collar Support Group™ that meets every Monday evening on Zoom.

We highly recommend Brent Cassity’s podcast, Nightmare Success, in which he interviews justice-impacted people from all walks of life. He is a White Collar Support Group member with a mission to be of service to our community. Please check it out on Spotify at or on your favorite podcast platform.