When I self-surrendered to federal prison, I assumed people would care about my white collar crime. I assumed they’d care about where I went to school, the amount of time I was serving, maybe even my background as a broker. I thought those details would carry some weight, maybe buy me a little respect or space.

They didn’t.

Once you cross that threshold—once the door locks behind you—none of it matters. That was the first wake-up call.

I was serving 18 months. My bunkmate was doing seven years. I learned quickly: if I opened my mouth to complain, to excuse, or to explain my situation, it would only backfire. The only thing that mattered was how I responded to the situation I was in—not how I got there.

And that’s where a lot of white collar defendants make their first major mistake.

Federal Prison Doesn’t Care About Your Résumé

There’s a tendency among white collar people to overestimate their importance. Maybe it’s the degrees, the titles, the salary history. In the free world, that stuff matters. In prison, it doesn’t.

I saw it over and over again: someone walks into the camp thinking they’re above the routine. They don’t say it out loud—at least not at first—but it shows. They push back on the work detail. They name-drop. They offer advice nobody asked for. They act like they’re there by mistake. They act like they deserve recognition for doing the bare minimum—like showing up to their job assignment or taking a class.

Those people stand out, and not in a good way.

When you walk into prison, nobody cares that you went to USC. They care if you’re respectful. If you mind your own business. If you stay low-key. And most of all, they care whether or not you think you’re better than everyone else.

The felony conviction is the great equalizer. The moment you arrive, you’re starting from zero—same as everyone else.

Offering Unsolicited Advice Will Cost You

I made a rule: never give advice unless asked. That single rule probably saved me more grief than anything else.

Too many white collar defendants go into prison thinking they can educate or “help” others. But what they’re really doing is trying to reassert the identity they had before their conviction. It’s a way of saying: I still matter. I still know things.

It’s not necessary. And it backfires fast.

People will test you. They’ll watch how you handle yourself when things don’t go your way. When the email kiosk is down. When someone cuts the chow line. When you get a bunkmate who snores or steals your soap. If your first instinct is to escalate, to complain, or to explain why you deserve something better, that’s when problems start.

Prison Staff See Through Performances

Don’t think you’re scoring points with staff for doing what’s expected of you. I see this mistake all the time.

Someone completes a course or shows up to their work detail on time and wants a pat on the back. They start lobbying for a better job. They want to be seen as the “good inmate.” But prison staff see through that. They’ve been around hundreds, if not thousands, of people trying to manipulate their image.

If you’re doing the work for recognition, it’s obvious. The people who earn quiet respect are the ones who keep their head down and do the job without trying to cash it in for something else.

If you need external validation to function in prison, you’re going to have a hard time.

Why This Matters for Sentencing and Beyond

You might be thinking: “Why does any of this matter to my sentencing or my release plan?”

Because the mindset you bring into prison affects everything else.

Probation officers read through your record for signs of entitlement. Judges listen closely during sentencing to see whether you’ve internalized the consequences of your actions. And the BOP looks at your behavior inside when evaluating halfway house eligibility or program placement.

If your attitude screams, “This is beneath me,” it will show—on paper and in person. And it will hurt you.

If you walk into prison thinking you’re starting from anything other than zero, you’re setting yourself up to fail. Not just socially, but with the very stakeholders whose opinion will shape what happens next in your life.

Back to the Beginning

I thought I’d be judged on my crime and sentence. Instead, I was judged on how I behaved—by bunkmates, staff, and everyone else in that environment. That reset was the hardest lesson I didn’t see coming.

The people who adjust well? They figure it out quickly. They stay humble, they listen more than they speak, and they don’t act like the rules are beneath them.

Ask yourself this: Are you preparing to start from zero? Or are you still hanging on to who you were?

Join our free weekly webinar every Tuesday at 11AM Pacific / 2PM Eastern. Or schedule a personal call with our team to talk through how to show staff and stakeholders you’re not walking into prison with the wrong mindset.