If you’re facing criminal charges or have already pleaded guilty, I have one question for you: What have you done to prepare for the best possible outcome?
Today, I spoke with a physician—someone who had earned scholarships, served our country, worked in emergency rooms, and even started a business. He’s a high achiever. Still, when it came to the criminal justice system, he admitted he didn’t fully understand what was coming.
Conversations with people like him is the reason I launched our nonprofit, Prison Professors.
I served 26 years in federal prison. I started at 23, after making terrible decisions in my early 20s. If I had understood the system better, I would have made different choices—choices that could have shortened my sentence and opened pathways to restoration. I created Prison Professors to help others make better decisions than I did, and to improve outcomes for all people who go into the system.
Today, I’m writing about what happens after a conviction and what a person could do—starting today—to influence a better future.
🎯 LESSON: Understand the Sentencing Process
When a person is convicted—whether by pleading guilty or after a jury verdict—several important steps follow:
1. Pre-Sentence Investigation (PSI)
A federal probation officer will investigate your background. This PSI becomes the foundation of your life in the system. The judge will rely on it. The Bureau of Prisons will rely on it. Your future probation officer will rely on it. You must understand it—and influence it.
Suggestion: Learn how to present your background, character, and goals during the PSI interview. Provide documentation. Submit a mitigation package. Show who you are beyond the conviction.
2. Sentencing Hearing
The sentencing judge will:
- Review your Presentence Investigation Report
- Hear objections from the prosecution and your defense
- Make findings of fact (which influence the sentencing guidelines)
- Consider any character reference letters or personal statement
- Offer you the opportunity to speak directly to the court
Suggestion: Prepare a thoughtful and remorseful allocution (statement to the court). Don’t relitigate the case—take responsibility for your actions, show insight, and express your plan for the future.
3. Transfer of Custody
When the judge says, “I sentence you to the custody of the Attorney General,” you move from the judicial system to the executive system. That means the Bureau of Prisons now controls your life—where you serve, whether you qualify for programs like RDAP, home confinement, or early release.
Suggestion: Spend time on PrisonProfessors.org to get ideas on how to build a mitigation strategy that will make you a strong candidate for relief mechanisms later—like early termination of supervised release or even clemency.
No one should work harder than you on this process. We’ll publish new lessons every day, but start thinking about the ways that you can influence what happens next. Below are some questions to prompt your thinking.
Consider the following questions as a prompt:
- What does the judge, probation officer, or Bureau of Prisons currently know about you—and what do you want them to know that could change how they view your potential for rehabilitation?
- If your sentencing outcome were determined solely by your personal effort and preparation, what would you start doing differently today?
- In what ways can you demonstrate that you’re more than the worst decision you’ve made?
- How might your life experience—before and after your conviction—help build a compelling case for mercy, redemption, or early release?
- What legacy do you want to begin building now, regardless of the sentence you’re facing?
