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Are These Really Prison Mistakes?

Some prison mistakes don't look like mistakes. Friendships, calls home, and Michael Santos's four quadrants for weighing risk and reward inside.

Justin Paperny

Founder White Collar Advice · October 6, 2026

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A prisoner helps you the day you surrender. He shows you where to eat and how laundry works. You start eating dinner with him.

A week later, you skip dinner. When he sees you, he asks, "Where were you, man?"

You barely know him, and you're already defending yourself.

That's the kind of mistake this post is about. iPhones, gambling, refusing your work assignment: you don't need me for those. At least I'd like to think you don't.

Some of what follows won't sound like a mistake to you. You decide. These situations happened. I mix in what Michael Santos taught me. When am I not?

The person who helps you on your first day in prison

You planned to read after dinner. He wants you to watch television with him. You go because you don't want to seem ungrateful. Saying no is tough.

By Friday, you haven't read much or added to your release plan. You've heard plenty about the people he dislikes.

Before you spend every meal with someone, watch him. Does he keep asking you for things? Does he get irritated when you have other plans? Are you repeating his complaints about people you've never had a problem with?

I would appreciate the help. I just wouldn't assume that meant we needed to spend every day together.

Then he asks for a favor: "Tell him you were with me yesterday."

You weren't. Now you're thinking about how much he helped you.

What do you do?

You could cover for him. He helped you, and it's one sentence.

You could say no and leave it there.

You could say no and tell him why.

You could start pulling away from him altogether.

Each choice costs you something. Which cost would you rather pay?

You don't have to tell your whole story

Someone tells you about his case, then asks about yours.

"How much money did you make?"

"Who testified?"

"What does your wife do?"

You answer because he answered yours (didn't our parents teach us to reciprocate?). A few days later, a guy you've never spoken with mentions your wife's business.

Go back to the moment he asked. You had choices.

You could answer everything, the way you did.

You could give him the short version: the charge, the sentence, nothing else.

You could say, "I'm not getting into all of that."

The last one may feel rude. You just met this person. I'd rather feel a little awkward than share something I wish I had kept to myself.

Same with correcting what people assume. Someone thinks you're rich. Someone thinks your lawyer bought you a short sentence. You want to explain until he gets it.

I wouldn't give him my financial history just to win that argument. He may repeat the explanation, too.

I'm talking about an irritating comment. A threat is a different situation.

"I've been down 15 years"

A prisoner who has served 15 years tells you a class is useless. Then he goes further. You're a tourist. You aren't here long enough to write about prison. And why are you so damn "upbeat"?

What do you do?

You could defend yourself: explain why the class matters, why your writing matters, why your attitude is your business.

You could ask him which classes he took and why they didn't help.

You could walk away, even if it makes you look weak.

That happened to me. I chose to walk away, and some men called me weak.

"Don't trust anyone" can go too far, too. I met Michael on my second day. His routine and his record made it easy to see he could help me. That's why I tell people to study their environment first.

Don't be Roman Fabrizi

It was July 9, 2008, around 3:45 in the afternoon, just after mail call. A new prisoner had transferred in from another prison. He stood about 20 feet from Michael and me, loud, telling anyone in range there was no deal he couldn't close. The jets he flew on. The models he slept with.

Michael asked whether I knew him. I didn't.

"That's Roman Fabrizi."

I thought, what an interesting name. I'm very literal. That's good and bad.

Walking the track that afternoon, Michael explained. Roman Fabrizi isn't a person. He's a kind of prisoner. He mocks the men trying to build something. He cozies up to staff, thinking it might get him more halfway house time or an earlier date home. He puts on airs.

I didn't know what "putting on airs" meant. Michael told me: acting superior. We're human beings. We can all become better.

I wrote about that walk in my prison journal the next day. The page hangs in my office.

You've already met one Roman Fabrizi in this post: the man calling you a tourist.

He's easy to spot in someone else. The harder question is whether you're turning into him.

Someone at your table is telling stories about his money, his deals, the people he knows. Your old life had some good stories, too.

What do you do?

You could top his story.

You could stretch yours a little. Nobody here can check.

You could let him talk and keep eating.

Don't be Roman Fabrizi. Don't put on airs.

What Michael taught me about the four quadrants

When I surrendered, I wasn't thinking about risk and reward. I was looking at another prisoner and wondering why he was getting out and I wasn't.

Michael introduced me to the quadrant exercise. He told me he picked up the idea from a Jim Cramer book he read in prison.

We used it to weigh how we spent our days. Michael pushed me to use my own judgment. He was serving his own sentence; his job wasn't to parent me.

I was serving 18 months. Michael was serving 45 years. Different time, different problems.

You may have a job waiting. You may want to finish with as few problems as possible and go back to it.

Someone else may have lost his license, his business, and the career he expected to have. He has to figure out how he'll earn a living.

That's going to affect which risks each person is willing to take.

Risk / reward

Low reward

High reward

High risk

Arguing about a rumor. You give someone details about your case and finances to prove him wrong. Now he has more to repeat, and you've gained little even if he believes you.

Michael publishing books in prison. He described transfers and time in the hole connected to his writing. He also earned money, helped support his wife, and had job offers waiting when he got out.

Low risk

Sleeping through another afternoon. The time passes. The letter you meant to answer is still sitting there.

Regular exercise. You use the time to come home healthier.

Use judgment with these. Sleeping because you're sick isn't sleeping because you've quit. The people around you change the risk, too.

When we discussed television, Michael raised something I hadn't considered: what was happening in the television room.

High risk, high reward: writing and publishing

Michael said his writing led to transfers and time in the hole.

I asked whether it was worth it. He said yes.

His writing earned money that helped his wife go to school. She became a nurse. He built relationships with people outside and said he had job offers waiting when he got out.

He kept writing knowing the cost. You might decide differently. That's why we talked about what each person wanted out of the time.

My book, Lessons from Prison, came out three days before my release on May 20, 2009. We worked on the book while I was inside and timed it to come out close to when I walked out.

You can write something today without publishing it today.

Read what you've written. Are you explaining what you're learning? Or taking shots at the men around you?

"Unlike most men here, I'm doing something productive."

I wouldn't publish that. You can describe your own work without insulting somebody else.

Low risk, high reward: exercise and getting ready for work

Exercise belongs here. Walking or running, within what your body can handle, means coming home healthier.

Other work in this quadrant doesn't need an announcement.

Say you can't go back to your old job. Spend time figuring out what work you can do, what you'll need to learn, and who might talk with you when you get home. Write to someone. Ask about the work. Give them something specific to respond to besides "I'm getting out soon and need a job."

Nobody in the unit needs to know.

High risk, low reward: complaining about your case

You're walking the track, going over everything that went wrong: the lawyer's fees, the judge, the person who cooperated. The other prisoner has his own list. You spend the whole walk on it and do it again tomorrow.

Then someone makes an assumption about your case, and you set out to prove him wrong. Now you're sharing details you never planned to share. Maybe he repeats them. Maybe he gets annoyed and it turns into an argument.

What was the upside? I'd rather spend that hour on something else.

Low risk, low reward: another afternoon of TV

You tell yourself you'll write your daughter after the game.

You don't. A few days later, her letter is still unanswered, and you've watched several games.

I don't think every game is a mistake. I do think you need to notice when you keep putting off the same thing.

I put watching ESPN all day in this quadrant. Michael pointed out that the television room itself could be a problem: men who wanted to control the TV, arguments over it.

Before you call it low risk, look at the room you're sitting in.

"Forget about the outside world"

"Just do your time."

I'd be careful with that advice.

Suppose you follow it. You stop asking about your children's schoolwork. You don't want to hear about bills you can't pay. Eventually, there isn't much to talk about when you call.

Maybe the man giving that advice stopped speaking with his own family. Does that mean you should stop speaking with yours?

Some days you won't be able to take more bad news. Tell your family that. But I wouldn't make shutting them out my plan for the whole sentence.

Michael kept working with people outside through decades in prison. His wife was part of the reason he kept writing.

"I'm in prison. Nothing I can do."

Your spouse tells you the car needs repairs and money is tight.

"I'm in prison. Nothing I can do."

You can't fix the car. You may not be able to pay for it. Can you listen without ending the conversation? Can you help look at the budget? Can you ask how it went on the next call?

I wouldn't pretend I could solve something I couldn't. But I also wouldn't want my family to hear that answer every time they called. Michael was supporting his wife through his writing. I was working on my book and asking people outside for help.

Talking with staff

You ask about your work assignment. You get the answer.

Then you keep talking: an argument in your unit, somebody else's case, a problem with your family.

Why add all of that?

You have to communicate with staff about legitimate needs. I wouldn't tell someone never to speak with them. I'd be careful about volunteering information after the reason for the conversation is over.

Advice nobody asked for

A new man arrives. Within a day you've decided what he's doing wrong. He calls his lawyer too often. He tells everyone about his case. He hasn't started a release plan.

You've been here longer. You know things he doesn't.

What do you do?

You could tell him. You're right, and he'll learn it eventually anyway.

You could wait until he asks.

You could offer once: "Come find me when you want to talk about release plans." Then leave it alone.

Ayn Rand put a line about this in the mouth of a character in Atlas Shrugged:

“It is not advisable to venture unsolicited opinions. You should spare yourself the embarrassing discovery of their exact value to your listener.”

This post is full of opinions. You asked for them when you clicked. The new man didn't.

Everybody wants your help

You help someone draft a letter. He tells his friends.

Now you're reading somebody else's paperwork, writing another letter, and sitting in on a dispute you weren't part of.

People tell you how smart you are. You like hearing it.

Your own release plan still isn't finished.

The next man shows up with his paperwork. What do you do?

You could keep saying yes. You're good at it, and it feels good to be needed.

You could set hours: other people's letters after your own work is done.

You could say, "I can't help with that today."

I understand wanting appreciation. I wanted too much of it in my twenties. Prison doesn't get rid of that on its own.

Invitations work the same way. You agree to every walk, every show, every conversation, then wonder why you never get to your own work.

"I'll walk with you at four. I'm writing until then."

You can say that to a friend.

Being the person with the latest news

You hear something about transfers or release dates. You tell five people.

They come back with questions you can't answer. You don't want to admit that, so you keep explaining.

Next time you hear something, you have choices.

You could pass it along the way you did.

You could pass it along with a warning: "I heard it. I don't know if it's true."

You could keep it to yourself until you check where it came from.

"Someone told me" may be all you've got. Which would you do?

Visits aren't always good news

In Chapter 1 of After the Fall, I write about Sam Pompeo visiting me at Taft. We sat with root beer and cheesecake while I told him I was considering staying longer to keep working with Michael.

Other prisoners were having different visits. Children struggling. Unpaid bills. A marriage ending. Men afraid to go home without the professional license they used to earn a living.

I had it easier. I didn't have a wife and children then. Sam could help me with work when I got home. I knew that.

Visits are where a lot of hard news lands, the kind that doesn't fit on a short call. You don't have to smile through every one.

But picture this: your family makes the drive, and you spend the visit complaining about your lawyer. They have things to tell you. You don't ask because you're still talking about sentencing.

Or they bring a problem from home and you say, "Why are you telling me this? I'm in prison."

You wanted the visit. They came. I'd want to hear what they've been dealing with, even if it wasn't what I wanted to hear that morning.

Making your family explain a missed call

Your wife misses your call because she's driving the kids.

When you reach her, you spend ten minutes asking why she didn't answer. She spends the call defending herself. You never ask about the children.

You wanted to hear from your family. Look at how you spent the call once you reached them.

They're still working, driving, and handling things you don't see.

Knowing prison better than the home you're returning to

You know your daily routine. You don't know what the rent will be when you get home.

"We'll figure that out when I'm released."

Why wait?

"What bills will I need to help pay in my first month?"

The number may be higher than you expected. You may learn your spouse has been borrowing money. Start those conversations before you walk out.

Doing the work and keeping it to yourself

You finish a release plan. You write about what you did. You have book reports and samples of skills you've been learning.

Your family hears, "I've been busy." They haven't seen any of it.

Who could use that work? Who could tell you what's missing?

Your spouse could read the budget and catch the expenses you left out. Someone helping you find work could read your explanation and tell you where it gets confusing.

Michael said he had job offers waiting when he got out. People outside knew what he'd been doing.

You don't have to publish everything or pass it around the unit. But the assets you're building for life after release need readers. Decide who.

Writing about honesty while avoiding a question at home

You finish a book report about honesty.

Your spouse has asked three times, "Is there anything else about the money I'm going to find out?"

You send another book report.

I'd answer the question. More writing doesn't get you out of that conversation.

That applies to my own advice about documenting. A man can fill notebooks and still avoid talking about what he did.

Would you make the same decision?

When Michael and I talked through the quadrants, I suggested the answer was to change high-risk behavior.

Michael said, "Or not."

He wanted me to weigh the options myself. He wasn't going to stop writing because it carried risk. He wanted to support his wife and have work waiting outside. He'd decided the writing was worth it.

Look back at your last week. Put what you did in the four quadrants.

Mostly television? Does that match what you said you wanted? Mostly writing? Who's going to read it? Took a risk? What were you after?

You may disagree with where I put something in the grid. Move it and tell me why on the webinar.

Which quadrant did most of your last week land in?

Written by

Justin Paperny

Founder White Collar Advice