I’ve been to more than 1,500 sentencing hearings. They start to sound the same after a while.

“Yeah, I bilked the government for $5,000.”
Or $100,000.
Or $4 million.

The story usually follows the same pattern: I did it because the pandemic hit, California shut my business down, and it wasn’t fair.

I understand the rationalization. I really do. Gavin Newsom eats indoors at a restaurant while everyone else is told to shut down? Sure, that stings. But that argument doesn’t carry much weight in a federal courtroom.

Over the years, I’ve sat in courtrooms before judges like Wilson, Carter, Holcomb, Selna, Gee, and many others. I’ve listened to what they actually say. And many of them have said, “I view bilking the government—especially Medicare—as worse than stealing from an individual.”

Why? Because when you exploit bureaucratic loopholes, you’re not just stealing money—you’re wasting taxpayer resources. You’re abusing trust. And when a judge believes you don’t understand that, your sentence goes up.

So if you’re going through a government investigation, or your sentencing is coming, here are three real ways people make things worse for themselves.

1. Cowering in Front of a Lawyer

Some lawyers don’t want to be bothered. They have templates. Boilerplate memorandums. A rhythm that’s worked for them for years.

When a client builds something unique—a record of volunteer work, a documented plan, a job offer from a nonprofit like Prison Professors Charitable Corporation—that’s when some lawyers complain.

“It makes my job harder.”

What they really mean is: It makes me have to think.

I’ve had lawyers text me on a Saturday night while I’m at taekwondo with my kids, angry that a client created something meaningful because now they have to integrate it. They’d rather stick to the script, cut and paste some “acceptance of responsibility” paragraphs, and call it a day.

But the reality is this: if you let your lawyer’s convenience determine your preparation, you’re asking for a longer sentence. You can’t outsource this part. You can’t hope someone else will care as much about your future as you do.

If you don’t hold your lawyer accountable and use the assets you’ve built, you’re giving up years.

2. Minimizing the Victims

The second mistake is pretending there aren’t any victims.

I hear it constantly in white-collar cases: “It’s not like I stole from some grandmother on the street corner.”

Yes, the government wastes money. Yes, bureaucracy is broken. But the person sitting on the bench doesn’t want to hear that. They want to know that you understand someone was harmed—taxpayers, patients, the integrity of a program.

If you dismiss the victims, even subtly, the judge sees it as arrogance. And arrogance is the shortest route to more time.

When judges hear “I’m sorry but…” they stop listening. That “but” tells them you still don’t get it.

If you can’t identify with the victims—even the unseen ones—you’ll never convince anyone you’ve changed.

3. Thinking You Have Time

The third way to get a longer federal prison sentence is believing you can wait.

Waiting to prepare for the probation interview.
Waiting to build a release plan.
Waiting to influence the people who control the plea agreement, the PSR, or the final sentence.

I hear it all the time: “I’ll deal with it when we get closer.”

That’s like showing up to run a marathon after sitting on the couch for six months. You can’t fake it. Judges can spot the difference between someone scrambling last minute and someone who’s been building quietly for months.

I tell clients: if your sentencing statement is the first time you’ve explained who you are and what you’ve done to change, it’s already too late.

When I went to prison, Judge Wilson told me, “You turned the other way for money. I’m making an example out of you.”

He was right. I had the time to build a record that showed I was different, and I didn’t. I waited.

Now, I work with men and women who made that same mistake. They sit in federal prison regretting how little they did when they had the chance.

Start Building Influence Now

Influence isn’t about speeches. It’s about documentation.

A judge doesn’t care about what you say in a five-minute allocution. They care about what you’ve done for the six months leading up to sentencing.

So build the asset. Document it. Share it. Create evidence that shows growth and contribution.

That’s what will persuade the people who decide your fate—the lawyer, the probation officer, the judge, and eventually, the case manager.

If you don’t, the government will tell your story for you. And they’ll have unlimited resources to do it.

The earlier you start, the better. The longer you wait, the more time you’ll serve.

I’ve watched this play out too many times to pretend otherwise.

Thank you,

Justin Paperny