The Last Day in Federal Prison Doesn’t Feel Like Freedom

Sixteen years ago today—May 19, 2009—I woke up in federal prison for the last time. I should have been excited. I was leaving. But the truth is, that day felt more like staring into the unknown than celebrating freedom.

I remember walking the dusty track at Taft Camp, slowly, intentionally. It reminded me of that scene in Castaway—Tom Hanks finally sailing away on a raft, glancing back at the island that nearly broke him. That was me, looking back at everything I had been through. It was hard not to reflect.

I sat on a backless swivel stool in my cubicle, stared out over the farmland, and kept thinking, It’s over. It didn’t feel real. You get so used to the rhythms of federal prison that even bad routines start to feel normal. I knew it was my last time calling home from that wall phone. My last chow hall meal. My last night on a steel bunk.

And I wasn’t just thinking about what I was leaving—I was thinking about everything I had promised to do when I got out.

The Prison Promise Everyone Makes

If you’ve served time—or you’re preparing to—you’ve probably made a few promises. I did. I swore I was going to start a business. Pay back what I owed. Rebuild trust. Cold-call lawyers. Share my story, honestly, even when it hurt. I told myself I’d turn this trainwreck into something useful.

And I meant it.

But here’s the reality: everyone makes promises in prison. The question is—will you actually try when it gets hard?

Most People Quit After Their First Rejection

Let me be real with you. Once I got out, the rejection came fast and hard. People didn’t care about my blog. Lawyers hung up on me. I had to call people who had zero interest in what I had to say—and still do it again the next day.

That’s where most people stop. They tell themselves, “I tried.”

But they didn’t. They hoped. Then they got hit with reality and tapped out.

Trying means showing up when no one’s watching. It means doing what you said you’d do even when you don’t get a gold star—or any acknowledgment at all. Trying is risking more embarrassment, knowing you might fail again.

That’s what I committed to on my last day in prison: just try.

What Actually Worked—and What Didn’t

Let me be honest: not everything I tried worked. But I kept showing up. I learned. I failed. I tried again. And over time, things changed.

Not because I had some master plan. But because I did the work. Every day. Despite the shame. Despite the fear of looking stupid. Despite the silence that usually followed every email and phone call.

That’s what most people miss. They think success after prison comes from being “inspired” or “having a vision.” No. It comes from doing the boring, uncomfortable work that no one applauds.

If You’re in Prison Now, This Is for You

If you’re in prison right now, don’t just talk about what you’re going to do when you come home. Everyone talks. Few actually follow through.

If you’re serious, prove it to yourself—now.
Write. Learn. Reflect. Get uncomfortable. Reach out to your victims. Get a mentor. Face the truth about why you’re there. Start something, anything, that puts you on the path you say you want to walk.

Because once you walk out those gates, you’re going to get hit with resistance you haven’t even imagined. People will ignore you. They’ll judge you. And worst of all, you’ll doubt yourself.

That’s when it matters. That’s when trying—really trying—is the only thing that separates those who grow from those who spiral.

16 Years Later, I’m Still Trying

Today, I run a company that helps people prepare for sentencing, prison, and what comes after. It didn’t happen because I had some genius idea. It happened because I kept trying.

Some days I still feel like that guy in Taft, staring out at farmland, unsure of what comes next. But I’m grateful I made that commitment.

So here’s the truth: you don’t need a perfect plan. You need effort. You need grit. And you need the humility to keep showing up even when the world doesn’t care.

Start now. Don’t wait until your last day in federal prison to figure out what you stand for.

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.