Sixteen years ago, I was sitting in a prison camp dining hall, wondering how I messed everything up. These days, I talk to people headed to that same place, but with far different bank balances. Some have nothing. Some have millions. A few, like the man I’m writing about today, are worth more than most of us can even picture.

Yes—billionaire. And still going to prison.

He called me recently, overwhelmed. Not about his sentence length. Not about prison conditions. About how far he’d drifted from who he used to be. And what he should do now that everything was crashing down.

This is what I told him. And it’s the same thing I’d tell you—whether you’re rich, broke, or somewhere in between.

“Simplify, Simplify”—It Still Holds Up in a Federal Prison

The advice came from Henry David Thoreau, long before any of us showed up: “Simplify, simplify.”

He wasn’t talking about prison, but the idea translates perfectly. Thoreau meant: stop needing so much. And that’s the heart of what I told this man as he prepared for his sentence.

You don’t need to spend $1,000 a month in the commissary. You don’t need to chase approval or status from other prisoners. You don’t need to carry all that ego with you.

He asked what he should focus on. I said: Spend $200 a month instead of $1,000. Read. Walk. Think. Say no when someone offers you a smuggled iPhone. You’re in prison to recalibrate. Start doing it now.

And honestly, he got it. He said: “I started with nothing, Justin. I grew up in poverty. But I forgot the mindset that got me out.” His success buried those early values in luxury and noise. Now, prison was going to strip it all back down.

I told him to let it.

The Trap of Trying to Recreate Comfort in Prison

Some people enter prison with the goal of keeping their outside life alive. They try to replicate comfort—stockpile commissary snacks, sign up for the “best” job, find influence, or worse, spend money for people to like them.

Let me be blunt: that mindset ruins people. You’re already in a place where the government stripped your freedom. Don’t waste more time trying to cling to image. No one’s impressed. Least of all the judge who might one day read your progress report.

If you walk into prison trying to maintain a lifestyle, you’re just making the fall harder. You’re also missing the point.

Prison is supposed to be a time to reset. To focus. To learn what actually matters again.

How Simplicity Shows Up in Federal Prison

Let me give you some practical examples. Because this isn’t abstract advice.

• Instead of buying 20 bags of chips, buy a dictionary.
  
• Instead of gossiping on the yard, write letters to your kids.
  
• Instead of watching TV for five hours, walk the track. Think. Plan. Read.
  
• Instead of hiding from the truth, document your daily thoughts. You’ll need them when it’s time to speak to the judge or probation.
  

This is how simplicity looks in a federal camp. It’s not about depriving yourself. It’s about needing less and seeing more.

It’s also how you start to rebuild trust—with your family, your future employer, and even yourself.

Let Prison Strip Away the Noise

When I left prison, I didn’t care about the brand of shirt I wore or the watch I had on. I cared about whether I was prepared to rebuild something real.

But if you don’t simplify while you’re inside, you’ll step out just as lost as when you went in.

The billionaire understood this. That’s what made the conversation real. He didn’t try to defend his wealth or ask how to keep his lifestyle alive in prison. He asked what values would actually help him come out better.

And I gave him the same answer I’d give anyone: Simplify. Not because it’s trendy. Because it works.

Strip away the ego. Drop the entitlement. Focus on who you were before things got distorted—and start acting like that person again.

Justin Paperny

P. S. If this resonates, join our team this Tuesday at 11a.m. Pacific, 2 p.m. Eastern. We host a free webinar to answer questions, share lessons from real cases, and help you avoid the most costly mistakes people make during a government investigation. Bring questions. Come ready to learn.