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 Prepare for Federal Prison 

Picture of Michael Santos

Michael Santos

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Howard Phillips Lovecraft was an American fiction writer who wrote horror stories. One of his published lines brought Mr. Lovecraft eternal fame:

“The oldest and strongest emotion of mankind is fear,” he wrote. “And the oldest and strongest kind of fear is fear of the unknown.”

If you’ve never been to prison before, then you may have some fear. That’s normal. Because if we’ve never been to prison, we don’t really know what to expect. We’ve seen prisons depicted in movies. Prison population levels have soared over the past several decades. As a result, artists portray prisons in film, television, music, and literature. When artists portray scenes from prison, they feature the sensational. They produce the scenes to elicit an emotion. Frequently, film producers want to elicit the emotion of fear.

Our team at Prison Professors provides you with a different perspective. If you’re going into the prison system, open your eyes to the best possible outcome. What does the best possible outcome look like in your case? If we can see the best possible outcome, we begin to realize that pathways to success exist.

Look at the success of our partners at Prison Professors.

Shon Hopwood was in his early 20s when he made some bad decisions. As he describes in his book, Law Man: Memoirs of a Jailhouse Lawyer, Shon used drugs. When a friend suggested that he rob banks, Shon agreed. He pleaded guilty to multiple armed bank robberies. Authorities locked him in prison with more than a decade to serve.

Our other partner, Justin Paperny graduated from USC. While there, he played on the varsity baseball team. After graduating, Justin became a stockbroker. As a stockbroker, he built a practice managing assets for professional athletes and hedge funds. He had an exciting career, with hundreds of millions in assets under management. Authorities targeted Justin for prosecution. Judicial proceedings brought his charming career to an abrupt halt. He pleaded guilty to securities fraud and a judge sentenced him to serve 18 months in federal prison.

Neither Shon nor Justin had been to prison before. One was going to prison for armed bank robbery. The other would serve time for a white-collar crime. Both men were afraid of what was to come. Prison would separate them from the people they love. It would separate them from the people who loved them. Neither knew anyone who had served time before. Yet both of them had seen the movies. They watched the television shows and they heard the stories.

Their outcomes on the other side of the journey, however, differed from what anyone would expect. Shon became the most successful jailhouse lawyer in history. He wrote briefs that won cases in District Courts, in Circuit Courts, and in the U.S. Supreme Court. Then, after completing his term, Shon went on to law school. He clerked for the D.C. Circuit Court. Georgetown Law School hired Shon. He’s now a law professor and advocate for reforms.

Justin chronicled his story in Lessons From Prison. When he went to prison, he feared the type of life he would lead upon release. Justin’s conviction for fraud resulted in the loss of his livelihood. He worried about how he would be able to earn a living. Like Shon, Justin, finished serving his sentence during the worst economic recession of our lifetime. Yet during the first few years since his release from prison, he began building businesses. Those businesses would generate millions in revenues. Clients for those businesses include law enforcement, the corporate sector, academia, law firms, the judiciary, and individuals who face time in prison.

  • Why did Shon and Justin experience a different outcome from what we see portrayed in media? They prepared for success!

I’m Michael Santos. My partners and I want to share everything we learned about mastering the prison experience. Like Shon and Justin, I went to prison as a young man. I started my prison journey in 1987, when I was 23. I didn’t get out of federal prison until 2013. Despite the 26 years that I served, every day felt productive. It felt productive because I wasn’t only preparing for prison. I was preparing for the success I would want to achieve in prison and beyond.

How Do We Prepare for Federal Prison:

We prepare for prison in the same way that we prepare for anything else in life. At Prison Professors, we urge people to define success. The person must ask the following question:

  • What is going to be the best possible outcome?

Answering that question is essential. None of us can change the past. But if we want to influence the future, we must begin by defining success. If we can define success, then we can engineer the path. That path should take us from where we are to where we want to go. Future chapters will define our methodical approach for defining success. We call it our Straight-A Guide. But for now, let’s focus our preparation on defining success.

Defining a successful outcome from prison requires us to complete a self-assessment. What does our life look like now?

  • If we’re a highly-educated person, that we may prepare in ways that differ from someone who doesn’t have a high school diploma.
  • If we have financial resources, we may prepare differently from someone who doesn’t have enough money to live in prison.
  • If we value close relationships with family, we may prepare differently from someone who wants to serve time alone.
  • If we have a sentence in excess of 10 years, we may prepare differently from someone who is serving one year.

Preparing for a successful journey through prison requires us to define success. And as shown above, success for one person may differ from another person’s success.

My partners and I all had different life experiences. Justin was a graduate from the University of Southern California and he was a licensed professional before he went to prison. Shon had a history of substance abuse and he was serving a sentence for armed bank robberies. I started selling cocaine when I was 20 and didn’t have much of an education when I started.

But one fact united each of us. Justin, Shon, and I hated being in prison. We wanted a different outcome from what others would expect of us. We wanted to return to society as law-abiding, tax-paying citizens. We didn’t want to live on the margins. We wanted success, and we prepared in ways that would be consistent with that outcome. Our preparations, however, began when we were already confined.

Prepare For Federal Prison Early:

The sooner a person can prepare, the better. Consider the oft-quoted adage on the best time to plant an oak tree. Do you know the best time to plant an oak tree? Some people say winter, some people say summer. Some people say fall, some people say spring.

A wise person knows the best time to plant an oak tree. It’s 20 years ago. The second best time to plant an oak tree is today.

The same thing goes with preparing for prison. The sooner a person can start thinking about the outcome that he wants to achieve, the better a person can prepare for a successful journey inside.

Good preparations serve a person well. Preparations will serve a person going to prison in the in the same way that a blueprint can serve a builder. It provides a guide of what steps we must take.

Not all people get to prison the same way. Some judges allow people to surrender at some point after the sentencing hearing. Through counsel, the defendant can ask the judge for time to prepare and get affairs in order. When judges allow people to surrender, they typically allow at least 30 days to pass. Some of our clients have been able to postpone their surrender to prison for a year or longer. There may be a variety of reasons that make sense for someone to delay their surrender date. They may want to complete a class. They may have family obligations. They may need to complete a business transaction.

If there isn’t a compelling reason to do the opposite, we encourage people to get started. Don’t delay the surrender if there isn’t a reason. While waiting to serve time, life can feel like it’s on hold. It’s hard to gain any traction in life when a prison term is looming ahead. For many people who must surrender to prison, the waiting can be interminable. It can feel like a person is serving time, but the time does not count. In Lessons From Prison, Justin describes how the period before surrendering to prison led to a depression. Others talk about drinking too much, or eating too much, or feeling traumatized with fear.

Each case is different, and we do not provide boilerplate guidance. But as a general rule, we find that it’s best to start serving the time as soon as possible. The sooner a person starts, the sooner a person can get on a path toward building a successful future.

We’ll provide some tips below. Some of those tips will be specific for people who have an option to surrender to prison. Other tips apply to all people, whether they’re surrendering to prison or whether they’re going to be taken into custody without notice. It’s important to remember that a judge has the discretion. The judge can leave a person out on bond for a lengthy period of time after the conviction. Or the judge can issue an order that results in an unexpected confinement. Consider the widely reported case of Martin Shkreli.

Martin Shkreli was widely castigated in the media. Headlines labeled him as the “Pharma Bro.” In 2017, a jury convicted him on charges related to fraud. While out on bond, he repeatedly appeared on social media. One post, supposedly, offered payment to anyone who could provide a piece of hair from Hillary Clinton. That post led prosecutors to say that Martin posed a thread. The judge agreed. He ordered the U.S. Marshals to take Martin into custody in September, long before his sentencing hearing. As a result, the Bureau of Prisons locked him inside a New York detention center.

Had Martin prepared better, the judge likely would have allowed him to surrender to a minimum-security camp. Life in a minimum-security camp offers considerably more liberty, and considerably less volatility than life inside of a detention center.

It’s always best to prepare. Knowledge translates into better decisions, and better decisions translate into better experiences.

Designation Details while you Prepare for Federal Prison:

Many defense attorneys will stop their representation at the sentencing hearing. Others will be willing to assist their clients a bit further. For those who have a good legal team in place, we offer some advice. Ask the defense attorney to get some confirmations from the Marshals and the BOP regarding the designation. A process unfolds after sentencing. The U.S. Marshals will forward the Judgment Order and the Presentence Investigation Report to the Bureau of Prisons designation center in Grand Prairie, Texas. Administrators in Texas will consider many different factors. Then they will identify an appropriate prison for the person to serve the sentence.

The staff in Grand Prairie will be responsible for submitting the appropriate paperwork to the designated prison. Sometimes human errors occur. Those errors can mean that the paperwork is not in order. If the paperwork is not in order when the defendant arrives at the institution, staff members may lock the individual in the Special Housing Unit. That means the person will be held on lockdown, without access to the telephone or recreation. Time will be much more difficult.

If possible, prepare in advance. Ask the defense attorney to confirm with the Bureau of Prisons and the U.S. Marshal service that all paperwork is in order. Our team has known many defendants who suffered because they were locked unnecessarily in Special Housing Units because they did not prepare in advance.

Identify Point of Contact (POC) as you Prepare for Federal Prison:

Identify a point of contact prior to confinement. Defendants may have a family member or friend who will serve as this point of contact. Let the POC know that they should expect to hear from you within two days. Defendants should understand that the Bureau of Prisons might not activate the phone or email system immediately. Still, if a defendant is on a prison compound, he will be in a community. Depending on the prison, a population level of between 100 and more than 1,000 people will serve time in the community. Someone will agree to help. They can have a family member reach out to your POC and let them know that you arrived safely and that you’re okay.

Create a plan for your POC to follow. If your POC does not hear from you after three days, ask your POC to take action. Your POC should contact your attorney. If you don’t have an attorney, you need an advocate who will help you. Your advocate should contact the Bureau of Prisons. Effective advocacy will lead the BOP to investigate why you’re not able to communicate. If you’re being held in the SHU because of misplaced paperwork, your advocate can take steps to correct the problem.

Alan was a client who could have used an advocate. Alan was convicted of healthcare fraud. He surrendered to a minimum-security camp to serve a 36-month sentence. Besides the instant offense, Alan did not have a criminal history. He expected to serve his time in the camp. Unfortunately, the BOP in Grand Prairie did not forward his presentence investigation report to the camp. As a result, when he surrendered to the camp, staff member locked him the Special Housing Unit. He remained in the Special Housing Unit for six weeks because the staff did not have a sense of urgency to fix the problem. Alan didn’t know any better, and he didn’t have a plan to fix the problem.

Consider Finances as you Prepare for Federal Prison:

Create a financial plan as soon as possible. The plan should take into consideration the financial responsibilities outside of prison, and the financial needs while in prison.

Every individual has a unique situation. Some people have family members to support. Others do not have any financial responsibilities outside of prison. Think this through. Craft a plan that works for the support group. Coordinate a budget, or plan to assist you through the journey.

It’s possible to live in prison without any financial resources. Yet financial resources can ease the burden significantly. Remember that prison is a microcosm of our broader society. An underground economy will exist in every prison. By understanding how that economy works, a person can avoid problems that can complicate life inside.

In our book Earning Freedom: Conquering a 45-Year Prison Term, I wrote about my experiences with the prison economy. I describe why I would spend about $600 each month to live in prison. Those expenditures allowed me to pay for the email system, the telephone system, postage, and to purchase commissary.

Other people live without resources. Some people have “hustles” in prison that allow them to function in that economy. They wash clothes, they clean, they cook for other people. Other people earn an income while working on prison jobs. Those jobs may pay anywhere from $5 a month to $200 per month. Jobs that pay $200 or more a month are relatively scarce, and staff members award those jobs in accordance with seniority. It may take ten years in prison before a person can get into one of the higher paying jobs.

A good plan will keep a person on track. Take steps to understand the financial opportunities and limitations in prison. I’ve written extensively about my experience in prison. When I left prison, after 26 years inside, I had more than $100,000 in after-tax savings. Those resources allowed me to start my life. The financial resources reflected my preparation. The preparations began with a visualization of how I wanted to emerge. Then I put my plan in place. Then I set priorities. Then I executed the plan. Make sure that you do the same.

Identify Reading Plan as you Prepare for Federal Prison:

A good planner will see advantages everywhere. We encourage you to plan your reading list. That plan worked well for our partner Shon Hopwood. He chose to read selectively in prison. That selected reading plan led to his developing knowledge of the law. By reading, he became an expert in writing appellate motions. While in prison, Shon wrote briefs that led to liberty for many people. His briefs won in U.S. District Courts, in Circuit Courts, and in the United States Supreme Court.

Likewise, Justin followed a disciplined reading schedule while in prison. He read books that would lead to his success upon release. What books will you read while you’re in prison? How will reading contribute to your success while in prison, and beyond?

In several of our programs, I describe the strategy that empowered me through prison. Each time I read a book, I would document the experience with a book report. The book report would follow a simple plan. I would answer three questions:

  • Why did I read the book?
  • What did I learn from reading the book?
  • How will reading the book contribute to my success upon release?

By responding to those questions, we show a disciplined, deliberate path to make time in prison work for you. It’s part of an excellent preparation strategy.

Journaling and Reputation Management While you Prepare for Federal Prison:

At the soonest possible time, anticipate the challenges that you’ll face upon release. Use your time inside to begin crafting your personal image. Anticipate the how prospective employers, creditors, business associates, and anyone else will perceive you. What will they find when they search your name on Google?

If you anticipate challenges in the future, you can begin sowing seeds today to overcome those challenges. That strategy worked well for Shon. It worked well for Justin. It worked well for me.

Each of us documented our journey in prison. Each of us chronicled our journey to show our disciplined, deliberate preparations inside. Those initiatives allowed us to overcome enormous obstacles. Shon persuaded a law school to admit him, he persuaded Bar to admit him, and he persuaded a federal judge to hire him. Justin’s journaling and strategies for reputation management while in prison opened enormous opportunities. Within three weeks of concluding 26 years in prison, I was teaching as an adjunct professor at San Francisco State University.

What led to those opportunities? Our journaling and our efforts to redefine our image made all the difference. Rather than judging us for the bad decisions that led to our prison term. People judged us for how we responded. We prepared while in prison.

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