Journal Entry: Saturday, May 11, 2024

Journal Entry

Preparing for Life in Federal Prison

The first time I saw Greg, I knew that he didn’t belong in prison. He was in his late 40s. Within seconds, I could tell that he was a person who was accustomed to leading–not following orders. By then, I had been incarcerated for more than 22 years. I was at the tail end of my time in prison, but he was only a few days into his term. He’d spent those first days in the Special Housing Unit, not understanding why authorities had placed him in solitary confinement.

We took a walk around the track. I introduced myself, offering to help him adjust. He told me that he had been somewhat familiar with me, as his family had visited my website prior to his surrender. I asked if he was a money guy, someone who operated a hedge fund or something of that sort. Greg told me that he had been CEO of a publicly traded company.

That’s when it clicked. I remembered reading about his case in the Wall Street Journal. Authorities had prosecuted Greg for an offense related to Sarbanes Oxley laws. Despite there not being any allegation of self enrichment or shareholder loss, prosecutors felt intent on putting him through a trial. After more than $50 million in legal fees, a federal judge sentenced Greg to serve 15 months in federal prison.

How does a person with his background prepare for federal prison?

It was different for me. My name is Michael Santos and I served 26 years in federal prison for crimes that I committed during the recklessness of youth. Yet I knew that I was guilty. When I was 20, I sold cocaine. I knew it was a crime and I knew it was my responsibility to use my time in prison to prepare for a life of meaning and relevance. 

I thought it would be infinitely harder to serve time in prison if a person hadn’t knowingly committed a crime. Yet in this era of big government, we have more investigations and more people going to prison.

To prepare for time in prison, a person should learn as much as possible before surrendering. It’s never too early, and it’s never too late to prepare for a better outcome. And since the passage of the First Step Act, people have more reason to think about the ways that they’re changing their life after a judge imposes a term. 

Many people will have discretion over the length of time that a person spends in a secure prison. By preparing before surrendering to prison, a person will be in a better position to self-advocate.

Mental and Emotional Preparation Before Surrendering to Federal Prison

Acceptance and Mindset:

Begin by accepting your situation. Face the reality that no one can change the past. Although attorneys may fight valiantly for relief from a sentence, a person going to prison must develop the fortitude to live in an environment that disappoints. Expect staff members to view you in the worst possible light. Anticipate that you’ll be around people with whom you wouldn’t associate outside of prison. Make the best of it. Cultivate a mindset of resilience and growth.

Educational Resources: 

Read books about prison life to set realistic expectations. ‘Prison Professors’ and other similar resources can offer valuable insights. I’ve written many books to show people how to live productively inside. Look for credible resources from people who built a documented record of thriving through crisis. Those preparations will help a person develop a plan and restore confidence. 

Measure Progress:

Create a system to memorialize the many ways that you’re using time in prison to prepare for a successful return to society. Our nonprofit built a platform to help. Visit Prison Professors Talent to build a profile. Use that profile to show the many ways that you engineered an extraordinary and compelling adjustment strategy. Always think about the next steps you can take to advance your life. This strategy will help you restore confidence, as you’ll focus on what you can do rather than dwell on what the system is doing to you.

Visit Prison Professors Talent to build your free profile, or send an email to to get started.

I make one promise to those who use Prison Professors: I will never lie to you, and I will never ask that you do anything that I did not do.

Critical Thinking:

  • If you’re inclined to memorialize your journey with Prison Professors Talent, consider using the following question as a prompt for your journal:

    In what ways will your adjustment strategy in federal prison advance you as a candidate for higher levels of success upon release?

I believe in you!

Michael Santos
Founder, Prison Professors