Every month, thousands of people reach out to White Collar Advice. Of those, 20% already served their time inside and are home from federal prison. A lot of them are struggling. When I ask what’s holding them back, the answer is almost always tied to how they spent their time in federal prison.
Many describe the same routine—playing cards, soccer, or becoming a great pickleball player. They’ll tell me how the days dragged on, how federal prison felt hopeless, or how they were stuck with a raw deal. I understand those feelings, but I have to ask: did that time prepare you for what comes next?
Pickleball doesn’t pay the bills. Neither does softball. You can’t spend years doing anything productive and expect to come out ready for life on the outside. That’s not me being harsh—that’s reality.
Time Inside: A Pattern
The people who call me often say the same thing: “I didn’t know what to do with my time.” Federal prison is a place where boredom dominates. It’s easy to fall into that trap, but the result is predictable. Those who spent their time coasting are the ones who struggle most when they get home and start supervision.
Reverse engineer your decisions. If you’re stuck now, trace it back to how you spent your time while inside. Did you develop skills? Did you create something you can build on now? Or did you spend those years distracted by low-value activities?
Federal prison beats some people down, but the pain doesn’t have to continue. I saw two types of people during my time inside: those who sit around complaining and those who figure out how to make something out of the time they’ve got.
For Those Going Inside
If you’re going to federal prison, think about how you’ll spend time inside. If you’re someone who doesn’t need to work when you get out—maybe because you’re financially set—don’t waste the opportunity. You’ve got life experience and knowledge that could help others. Teach. Inspire. Give back. Complaining about the food or the rules won’t make a difference, but mentoring someone might.
For everyone else, focus on what’s ahead. Embrace the quadrant theory to guide your choices inside. Ask yourself: is this activity high risk, high reward? Low risk, low reward? Or somewhere in between? Choose activities that create value for the long term, even if they’re challenging now.
Use your time inside to develop skills that matter. Learn something new. Write. Read. Build something tangible you can point to when someone asks what you did with your time inside.
Why Your Time Inside Matters
The truth is, most people get out of federal prison and face an uphill battle. The stigma is real. Finding work can be hard. Rebuilding trust with family takes time. That’s why wasting years on games or aimless routines doesn’t work. It’s not about becoming an expert at dominoes or getting through one more card game; it’s about finding something that prepares you for the life you’ll have when you get out. That’ why writing and documenting the journey is so important.
The people who struggle the most are often the ones who leaned on excuses. They tell me the prison environment made it impossible to do anything productive. They say they felt defeated from the start. And while those feelings are valid, I can’t help but push back: others in the same environment found a way to leave stronger than they arrived.
What’s the Alternative?
If you have to go to prison use the time wisely. Don’t make the mistake of thinking that federal prison is just about waiting for release. That time is your chance to create and build, whether it’s a plan, a skill, or proof that you’re different than the DOJ’s press releases.
And if you’re already out and feeling stuck, start today. Reflect on what you did with your time and what you can do now. If you spent those years doing nothing, it’s not too late to begin. Reverse engineer your decisions, figure out what went wrong, and take steps to fix it.
Complaining is easy. Doing something with your time is hard. But in the end, only one of those choices gives you a shot at overcoming the consequences of a conviction. Make the time count. It’s not just about serving time—it’s about letting the time serve you.
Join our weekly webinar and listen to our New York Times podcast to learn more. Oh yes, one more thing: if you can give back, learn more about Prison Professors Charity.
Justin Paperny
