If you’re going to federal prison, we encourage you to prepare. That’s why we host weekly webinars, give away free tools, and work with people one-on-one. This is not something you want to wing.
The people who serve time the right way don’t just get ready by learning rules or packing a bag. They get ready by changing how they think, how they observe, and how they respond. That’s what allows them to build a daily record that shows who they are—and why they’re worthy of trust, responsibility, and in some cases, direct placement to home confinement instead of the halfway house under the Bureau of Prisons’ new directive.
Three skills make that possible:
- Observation
- Self-awareness
- Temperament
Neglect them, and you’re more likely to waste time or make avoidable mistakes. Practice them, and you’ll put yourself in a position to earn more liberty.
Let’s walk through each one.
1. Observation: Stop Talking. Start Watching.
Within your first few minutes or hours of going to federal prison, someone will start talking at you. It might be about housing, commissary, prison advice, or what they think you should do. You’ll see people sizing each other up, forming groups, giving instructions. Most of it won’t help you.
Your job—especially in those early weeks—is to observe.
Who works and shows up on time? Who keeps to themselves and lives by a routine? Who tells the same story every day, and who produces quietly? Who seems respected without needing to ask for it?
Observation is how you learn without stepping into problems. As Epictetus said, “We have two ears and one mouth so that we can listen twice as much as we speak.”
This doesn’t mean hiding. It means being deliberate. You’re there to study the environment and make decisions based on facts, not fear or assumptions.
Ask yourself:
Are you prepared to observe before you speak?
Are you clear on how to evaluate who you associate with?
Because a few early decisions—who you talk to, who you align with—can affect your entire sentence.
2. Self-Awareness: Stop Blaming. Start Evaluating.
Most people don’t get in trouble in federal prison because of the rules. They get in trouble because they repeat the same habits that brought them there in the first place.
If you don’t build a routine of self-reflection, you’ll miss the opportunity to document how you’re growing. It means asking questions every day:
What did I do today that I’m proud of?
Where did I fall short?
Who did I spend time with—and why?
Did I keep my word to myself?
This is what I meant in Ethics in Motion when summarized Aristotle’s lessons: You don’t become ethical by reading about ethics. You become ethical by practicing ethical decisions. Just like you don’t learn to hit by reading about baseball. You step into the box. You swing. You adjust.
If you’re not writing and evaluating every day, your file won’t reflect progress. You’ll miss the chance to prove you deserve more leniency.
Ask yourself this is you are going to federal prison.
Are you documenting the habits, routines, and decisions that demonstrate you are making the most of the experience?
Are you treating each day as part of the record?
If not, you’re hoping your character will be noticed. That’s not how it works.
3. Temperament: Stop Complaining. Start Practicing Decency.
This is the part most people ignore.
You can observe. You can journal. But if your attitude fluctuates with every frustration—if you’re short-tempered, defensive, or sarcastic—none of that other work will matter.
In How to Grow Old, Cicero wrote:
“Older people who are reasonable, good-tempered, and gracious will bear aging well. Those who are mean-spirited and irritable will be unhappy at every period of their lives.” (p. 17)
I saw the same in federal prison.
The people who were kind, even-keeled, and respectful—especially toward those who hadn’t had the advantages they had—earned trust. Not because they were perfect. But because they were consistent.
On the other hand, the moody, bitter, irritable prisoners? They struggled. They stayed in conflict. They sabotaged their own opportunities–more about this on our next webinar.
Ask yourself:
Do you want people to remember you as decent?
Or do you want to become one more person staff and prisoners quietly avoid?
Freedom Is Coming. Don’t Miss It by Complaining.
There’s one more passage from Cicero that stuck with me. On page 11, he writes:
“Everyone hopes to reach old age, but when it comes most of us complain about it. People can be so foolish and inconsistent.”
That line describes what I saw in federal prison. People spend years waiting for the end of their sentence. But when it comes, they start complaining again. About the halfway house. About probation. About the rules they’ll have to follow once they get out.
They miss the whole point.
They wanted liberty, yet rather than appreciate coming to the end of prison, then lament over what’s next.
Ask yourself:
When your sentence ends, will you be ready to step forward—or still stuck in complaint?
If you practice observation, self-awareness, and temperament every day, you’ll build more than discipline. You’ll build a documented record of growth. That’s what matters to stakeholders. That’s how you show—not just say—you’re worthy of more liberty.
If you want help building that record, join our next webinar. We’ll show you how people inside are already using this approach to earn more trust—and in some cases, preparing to move straight to home confinement.
As simple as it sounds, this whole process starts by trying.
Justin
