Justice Notes: Preparing for Prison
A White-Collar Journal forum for criminal justice, lived experience, and the personal search for redemption
Incarceration is one of the few life transitions for which there is almost no official preparation. What follows is not legal advice, nor an endorsement of the system, but a practical guide written by someone who entered federal prison unprepared, and hopes others don’t have to
A GUIDE FOR NEW INMATES
I spent eighteen months in a federal prison camp. I still remember my arrival vividly, and how unprepared I was for it. There is almost no guidance offered by the government to help people transition into incarceration. Everyone endures a period of adjustment, often blindly. What follows is a practical guide for prospective “new arrivals,” based entirely on lived experience. My hope is that it makes the transition less stressful and a little more humane.
FIRST: RESET YOUR ASSUMPTIONS
Don’t assume prison is populated only by “bad people.”
Many good people are incarcerated—people who made mistakes, feel genuine remorse, and are determined to make amends and return to better lives.
Also know this: the days go slow, but the weeks go fast. I didn’t believe that when I first heard it, but it’s true. The advice below helps manage the daily tedium so time doesn’t defeat you mentally.
HOW TO CARRY YOURSELF
Keep a low profile—especially at the beginning.
People who call attention to themselves are rarely received well. Assimilate quietly. Observe more than you speak.
In most facilities, inmates greet newcomers warmly and offer help. There is a real brotherhood/sisterhood inside. Accept help when it’s offered—and return the favor when you can.
That said, choose friends carefully. Take your time. Avoid inmates who are essentially doing life on the installment plan—the incorrigible.
ESTABLISH A ROUTINE QUICKLY-Routine is everything.
You’ll be required to work. Camps are working facilities. Sometimes you’re assigned a job; sometimes you can request one. Ask other inmates about their jobs and try to find one you’re comfortable with.
Once you establish:
a job
reading time
exercise
a small, reliable social circle
…the time moves more predictably—and more tolerably.
READING IS NOT OPTIONAL
There is an enormous amount of dead time in prison. Reading isn’t a hobby—it’s survival.
There will be a library. Friends and family can send books and magazines directly from publishers. Take advantage of that. Your mind needs somewhere to go.
STAFF: BE A GHOST
Inmates never win arguments with staff.
Some officers are professional. A few are nasty. None are your friends.
Challenging staff—guards or administration—is always a mistake. Be invisible. Do your time. Go home.
CONFLICT AND RELATIONSHIPS
Real friendships are possible in prison—inevitable, even. Shared hardship creates real bonds.
If you have an issue with another inmate, deal with it directly. Do not involve staff. Reporting other inmates is anathema to prison culture and will isolate you quickly.
COMMISSARY BASICS-Prison Store
You’ll receive basic toiletries and clothing, but you’ll want commissary items.
Key things to know:
Commissary runs once a week
You’ll need to get by with what you’re issued at first
Other inmates will usually help until you have access
The easiest way to fund commissary is for family to wire money via Western Union. Instructions will be posted or shared by inmates—it’s straightforward once you see it.
Be cautious if other inmates ask you to purchase items for them. Avoid these arrangements unless you are completely comfortable.
FAMILY ON THE OUTSIDE
One of the hardest parts of prison is the inability to help those you love.
Do what you can:
Reassure them you’re okay
Avoid sharing every bad day
Don’t escalate issues unless intervention is truly necessary
Calls from family to prison administration are rarely helpful and often counterproductive.
TAKE CARE OF YOUR BODY AND MIND
Oddly enough, prison can be an opportunity to improve your health.
There’s no alcohol. No smoking. Plenty of time to exercise. Many inmates leave in better physical condition than when they arrived.
More importantly, prison gives you something few people ever have: time to think.
Use it. Reflect. Build a next-life plan.
FINAL THOUGHTS
There will be dark moments—times when the weight of incarceration feels overwhelming. Those moments pass, mostly through routine and human connection.
If you enter prison with:
a realistic perspective
a steady attitude
a willingness to adapt
…you can emerge stronger, more self-aware, and more grounded.
Thousands have done it. And many of us are rooting for you.
If you’re drawn to the idea of storytelling as self-reckoning, I’d love to hear your thoughts in the comments.
Thank you for reading White-Collar Journal. Subscribing is free, and I hope you’ll continue with me as I explore stories of incarceration, justice, and redemption.
If this piece resonated with you, consider sharing it or leaving a comment. To support this work and help spread awareness about justice reform for white-collar defendants, subscribe to White-Collar Journal and stay connected. John DiMenna is a member of the White Collar Support Group.
To leave a comment, Substack may ask you to verify your email address (a one-time step to prevent spam). You don’t need to subscribe or create an account. Just check your inbox for a one-time link.
