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 Tips Before Surrendering to Prison 

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Michael Santos

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Are you facing time in prison? Learn from our top-ten checklist on how to prepare before surrendering to prison.

Top-Ten Checklist Before Surrendering to Prison

Step 1: Prepare to Document the Journey

By the time a federal judge imposes a prison term, the process will exhaust a person. He or she will have gone through the following steps:

  • An investigation,
  • A criminal charge,
  • A plea hearing,
  • A trial or guilty plea,
  • A presentence investigation,
  • A sentencing process

At a minimum, those procedures will span over several months. In some cases, the dark cloud of a criminal prosecution in federal court may last several years. We’ve known some people that have had to live with the complications for a decade before they surrendered to prison.

The sooner a person begins to prepare, the sooner a person will have a solid plan to work toward a better outcome. We can measure a better outcome in many ways. Although we’d like to change the past and avoid a criminal charge altogether—no one can do that. On the other hand, opportunities may exist to influence:

  • A more successful journey through prison,
  • An earlier release date,
  • A higher level of liberty upon release
  • A more persuasive case for early termination of Supervised Release
  • A faster pathway to a successful career

Before surrendering to prison, we all should think of steps we can take to architect a more successful journey. With prison-reform legislation like the First Step Act (FSA), judges have an opportunity to consider compassionate release. People with self-discipline sow seeds to make themselves more attractive as candidates for relief. To succeed, the person should engineer a series of events to document the journey.

I would never ask anyone to do anything that I didn’t do. Anyone can review our various web platforms to see how thoroughly I began documenting the journey early. For example, see the following links:

What do those links have in common? They show a disciplined, deliberate pathway to reconcile with society. As a result of documenting the journey, I had more success in getting a higher level of liberty early, and also in building many businesses upon release.

With the First Step Act, it’s more important than ever to learn about self-advocacy.

For these reasons, I encourage people to engineer pathways to show the following:

  1. In what ways are you defining the best possible outcome?
  2. How do you intend to document that journey?
  3. What priorities must you put in place, before the start of the journey?
  4. What tools, tactics, and resources can you create to differentiate yourself from every other person that wants to get out early?
  5. How will you show that you’ve executed the plan?
  6. In what ways will you invite the world to hold you accountable?
  7. How transparent will you make your execution strategy?
  8. In what ways will the documentation you create advance your candidacy for relief?
  9. How will your strategy show that you’ve worked hard to make amends?
  10. In what ways will stakeholders see you as being different from expectations of people that have gone into the system?

If you can answer those questions with authority, you’ve taken a giant step toward preparing before you surrender. If you have not, then please read articles on our various web platforms to learn more about the steps you can take to emerge successfully. The remaining steps on our plan may help, too.

Step 2: Establish a Primary Point of Contact

Before surrendering to prison, a person should appoint a primary point of contact. That point of contact may be a spouse, a parent, a best friend, or a lawyer. The person should help the point of contact understand what to expect. If things don’t go right, the point of contact must have a plan in place.

What does a person going to prison, and a point of contact need to know?

To start, the person needs to make sure that an attorney is standing by ready to help. Ask a lawyer to confirm that the prison has proper paperwork in order.

After a sentencing hearing in federal court, The United States Marshal Service has the responsibility of sending a Presentence Investigation Report (PSR) along with the Judgment and Commitment Order—also known as the J&C—to the Bureau of Prisons. The Bureau of Prisons has a central office located in Grand Prairie, Texas. Administrators in Grand Prairie will assess where to send a person.

The staff members in Grand Prairie have the responsibility to classify every person that is going into federal prison. After assigning a security level, the Bureau of Prisons will assign a prison. In the federal system, administrators use the vernacular “designation.”

To learn more about classification systems, please read our article:

A person should know what will follow after administrators designate a person to serve the sentence in a specific institution.

Ideally, the defense attorney will confirm with a staff member from the BOP’s office in Grand Prairie. Staff members should send paperwork to the prison in advance. If the prison does not have the PSR or the J&C, or both, a person will go through a bit of difficulty.

If the paperwork is not in order at the local institution, staff members will lock the person in the Special Housing Unit, also known as “the hole.” The person will remain in that solitary cell until somebody fixes the problem.

The person that prepares well will have a plan in place. A good plan will limit the possibility of serving time in the hole when a person should be in the general population.

In normal circumstances, the point of contact should expect a phone call within 24 hours of the day the person surrenders. If the person does not receive that phone call, make sure the point of contact knows how to follow the plan.

First, the point of contact should call the attorney. Ask the attorney to check with the prison and with BOP staff in Grand Prairie, Texas. If the attorney doesn’t act, the point of contact should act. Launch a campaign to learn what has happened.

It’s possible that the person doesn’t have access to the phone on the first day inside. That’s okay. If the person is in the general population, he can ask someone for help. Another person can ask his family member to call the contact person. There is always a way to get the message out—unless the person is in the special housing unit, or the prison is on some kind of special operation schedule. Either way, a person should prepare a point of contact in the event that something doesn’t go right.

The above steps are kind of like an insurance policy. If all goes according to plan, a person doesn’t need to exercise this insurance policy. Although I don’t have precise statistics, we can estimate that all goes according to plan eight out of 10 times. If things do not go well on the day of surrender, make sure that the point of contact person knows the plan, and knows how to act. After all, the BOP can make a clerical error. Errors happen.

The well-prepared person understands how to prepare and to make sure that his contact person knows how to prepare. Expect challenges from the BOP. It’s like dealing with the DMV—only times 100. A person must succeed anyway. That’s the number one thing to prepare for before surrendering to prison.

Step 3: Understand Financial Implications

Prepare well with regard to keeping finances in order. Finances don’t only include all the resources that a person will need while serving a prison term. Rather, a person should consider the resources family or loved ones will need at home. A person should prepare these financial arrangements before surrendering to prison.

People convicted of white-collar crimes that involve deceit, or abuse of trust, may undergo particular problems. Banks and brokerage houses have been known to “fire” people, making them move accounts if the person has a conviction for a fraud-related offense. Courts impose sentences on people of wealth, just as they impose sentences on people without means. Despite a high net worth, a person that has a fraud conviction may find that banks and brokerage houses fire them. Without warning, the financial institutions will order the person to withdraw money from the bank within 30 days.

Losing financial relationships can stress a person out at any time. While in custody, a person will be far less capable of opening new accounts. For that reason, we recommend that people create several options:

  • Open accounts at multiple financial institutions.
    • By opening several accounts, a person may protect himself. If one institution closes an account, the person can transfer resources to another existing account.
  • Provide Power of Attorney to trusted people that can move funds as necessary.
  • Create alternative strategies, such as owning different types of asset classes that will retain value during the term of imprisonment, or appreciate in value during the term of imprisonment.

People without money in prison have more stress. That stress can lead to problems. The person who does not have a financial plan becomes more vulnerable to problems while serving a sentence. Staff members sometimes issue disciplinary infractions when they hear a person in prison giving financial instructions over the telephone. Staff members may accuse a person of “running a business from prison” if they hear a person instructing a spouse to transfer funds from one account to another account. People who do not understand rules can face discipline. Disciplinary charges can lead to loss of phone access, the loss of email access. It can result in a loss of visiting privileges.

Every person should know and understand the prison’s rules. They can find those rules from the “inmate handbook,” available from the BOP’s website link for each prison.

A person can live in prison without any money. But if a person doesn’t have access to money, the person may not be able to access the phone. The person cannot send mail or shop in the prison store. Like living in every American city, money makes life easier.

A person should set a budget. As an active writer, I spent $600 per month in prison, because I spent money to use the e-mail system, I used the phone as much as possible, and I purchased all that I could from the commissary.

While serving a sentence, a person can:

  • Write books.
  • Author business plans.
  • Create business opportunities that generate revenues or promise to generate revenues upon release

I learned that having money in my prison account helped me to achieve more goals.

Other people don’t have to spend $600 per month. A small budget would be $100 per month. To use phone and email, expect to spend $200 per month. To shop in the store, budget another $200 to $500 per month.

Understand the store and spending limits prior to going inside. To start the prison journey, get the money ready. Ask someone to send the money. Send money by Western Union late on the day of reporting. Send $400 on the day of surrender. Add money into the prison account each month. Western Union is fast and certain, but the service charges a fee for each transaction. After the first month, send money through the mail to the Central Lockbox in Iowa, at the address located on the BOP website, at

We offer a tutorial for sending money in prison. Access the information through the following link:

Step 4: Create Deliberate Reading Lists

Establish a reading plan before surrendering to prison. Create a methodical, deliberate plan. Reading will empower a person through the journey. Begin each year with a reading plan.

  • How many books will you read each year?
  • What purpose will your reading list serve?
  • What steps will you take to record what you’ve read?

I had a process in prison. Each time I read a book I wrote a report. The report would answer three questions:

  1. Why did I read the book?
  2. What did I learn from reading the book?
  3. How will the book contribute to my success upon release?

Through our coursework, we show how that strategy can lead to higher levels of liberty upon release, and help a person overcome some of the challenges of confinement. I used this strategy to launch my career, and also to accelerate the “early termination” of supervised release.

A person should share the reading plan with loved ones and those in the support group. Invite others to follow the reading plan. Urging them to hold the person accountable during the sentence length.

The reading list should help a person climb through the sentence, and also to restore dignity. If a person serves a five-year sentence, the person should have a five-year reading plan before surrendering. Commit to reading, and a person will remove some pains of confinement. The wise person who prepares well will identify books that bring value and accelerate progress toward goals. Supplement that list with additional books later. Extend this plan each year, always striving to make progress toward completing a reading list.

Create a plan for receiving books while inside. Instruct family members or friends to order books from Amazon. Ordering from Amazon limits problems. Staff members in the federal prison system have familiarity with Amazon. People should not order more than two paperback books at a given time. Family members should not send magazines because some BOP staff will reject them. The person who prepares well will teach members of a support group how to order books.

Ten books I recommend to start a reading list:

  1. Earning Freedom: Conquering a 45-Year Prison Term
    • I authored this book to reveal strategies masterminds taught, and to show how those strategies empowered me while I climbed through multiple decades in prison.
  2. Law Man: Memoir of a Jailhouse Lawyer
    • My friend Shon Hopwood shares his story of how he learned how to become an exceptional appellate attorney while serving 10 years for armed bank robbery.
  3. On Writing
    • Stephen King, the well-known novelist shares the story of how he became an author, and the steps others can take to become an author.
  4. Elon Musk: Tesla, SpaceX and the Quest for a Fantastic Future
    • An outstanding biography that helps us understand the importance of critical-thinking and developing a strong work ethic.
  5. How Google Works
    • Eric Schmidt, the former CEO of Google, reveals strategies the company used to become one of the world’s most dominant companies.
  6. Extreme Ownership: How U.S. Navy SEALs Lead and Win
    • Jocko Willink, a Navy Seal, helps us understand the importance of personal responsibility and accountability.
  7. The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph
    • Ryan Holiday helps us understand the ancient Stoics, and how they taught us the importance of being self-directed, and self-reliant, and living with the world as it exists—rather than as we want it to be.
  8. Shoe Dog
    • We learn from the biography of Phil Knight, the founder of Nike, one of America’s greatest brands.
  9. Execution: The Discipline of Getting Things Done
    • Business leader Larry Bossidy helps us understand how to think like a CEO and to be more intentional with our decisions.
  10. Start with Why: How Great Leaders Inspire Everyone to Take Action
    • Simon Sinek helps us understand the importance of the decisions we make. He shows how and why some companies become great, while other companies flounder. We can use those lessons to make it through challenging times.

The list above skews heavily toward business, personal development, and optimal performance. Those kinds of books empowered me while I climbed through 9,500 days in prison. I’m confident this genre of books can help others.

Step 5: Create Journaling and Writing Plan

Begin with a writing plan. In Step 1, I recommend creating a platform to document the journey. If a person journals, the person should have a plan to publish. That publishing plan will keep family members apprised, showing the person isn’t languishing. Further, the journaling exercise may help a person document a strategic plan of preparing for success. By memorializing the incremental progress, the person may advance possibilities of persuading a judge why the person stands worthy of compassionate release.

Be extraordinary. Create a compelling case! If you’d like our course on the importance of journaling, click the following link:

By writing, a person shows how to build strength through struggle. Journaling may inspire others. Prison presents an awesome opportunity to write a memoir. The memoir will lead to success after prison. We live in a world of transparency. Anyone can perform a Google search of anyone else. The criminal charge will surface. Rather than fearing search-engine results, take a proactive approach. Begin sowing seeds for a better outcome.

I wrote more than 20 books from inside prison. I wrote books under my name; other people in prison paid me to write books for them. Learn how publishing can lead to new business opportunities and to the restoration of a reputation.

When writing, do not think of selling the work. Rather, think of how investing time to memorialize a journey may work to sell the author as a candidate for mercy. By writing deliberately, a person can:

  • Show how he or she has worked to reconcile with society,
  • Build a story that helps others want to reach their highest potential,
  • Improves a social reputation,
  • Helps to ease a transition back into society, at the soonest possible time.

The journaling exercise may also serve as an outstanding tool to persuade a probation officer to grant higher levels of liberty, at the soonest possible time. That strategy worked for me, and I’m convinced that it can work for others, too.

Success doesn’t happen by accident. Every decision influences our journey through prison. It also opens prospects for liberty upon a transition to society. Everyone on our team encourages people to blog and journal. Writing will prove therapeutic. Create plans to succeed from prison.

Step 6: Prepare Personal Belongings

Before surrendering to prison, a prudent person would think of the practical necessities. If a person anticipates that the prison will not offer anything more than basic survival things, the person will not be disappointed. Most prisons will offer opportunities to purchase items from a commissary. A person can get an idea of what the prison makes available by visiting the BOP’s website at, and looking for an institution. Many of the local institutions will publish a commissary list. Although some variations occur from one institution to the next, for the most part, those commissary lists are barren. For an example of a prison commissary list and a prison handbook, click the links below:

When it comes to personal hygiene items, a person will have minimal access. If a person needs reading glasses, bring two pairs if possible upon surrendering. Choose inexpensive, sturdy glasses. The BOP commissary will likely sell reading glasses. If a person requires a stronger lens, bring your prescription glasses. Again, choose sturdy rather than decorative frames.

A person may bring religious items, such as a book of worship. Staff may authorize a person to wear a religious necklace, provided the necklace isn’t flashy or worth more than $100. People who surrender to prison will encounter fewer problems if they do not attempt to bring more than necessary.

With regard to policies for a wedding ring, the BOP policy holds that the ring cannot be worth more than $100. That policy has been in place for longer than 30 years. It existed when I began serving my sentence in 1987. Officials are not going to request a receipt to show the value. Still, a person shouldn’t wear anything too flamboyant. The wedding ring cannot have gemstones.

Do not bring checks, cell phones, or credit cards. Be Spartan in belongings. A person can ease an adjustment with stoicism. Family members can mail photos on plain sheets of paper.

Step 7: Understand Medical Preparations

If a person needs medication, the person should take precautionary steps of visiting the BOP website to learn about the types of medications that the BOP authorizes. As a bureaucracy, the BOP documents everything in its policy statements. The following link shows different medications that administrators authorize:

Prior to surrendering to prison, a person should go over the formulary with his or her physician. The physician may work through a detailed plan, helping to document the reason for the medication and why it’s necessary. If the physician knows that the Bureau of Prisons will not authorize the medication, the physician may create an alternative—offering a substitute that the prison system will authorize. Outstanding preparation may even help an attorney get a recommendation from the sentencing judge.

Success in prison begins with excellent preparation. If a person has extensive medical needs, the person may want to work toward serving the sentence in a facility that offers higher levels of medical care. In an interview we conducted with a former director of the Bureau of Prisons, we discussed the different care levels:

Our team recommends that each person should take precautions before surrendering. Learn as much as possible about the opportunities to get treatment for medical complications while serving the sentence. The more a person knows and understands, the more successful a person becomes at launching or coordinating a self-advocacy campaign.

During the 26 years that I served in prison, I distinctly remember the story of one person who prepared well. He knew that he would be serving a five-year sentence. Knowing that he wanted to recalibrate his life while serving the sentence, he set a goal of getting a knee replacement. The cost of the surgery would have been prohibitive to him before he surrendered—as he had lost everything as a result of the conviction. He adhered to the same process we encourage others to follow:

  • Define best outcomes
  • Create a strategy and document it
  • Create tools, tactics, and resources
  • Execute the plan

That plan served him well. Before surrendering, he got his doctor to write a letter memorializing the necessity of knee-replacement surgery. He created a plan that allowed him to serve his sentence in a medical facility. He launched a coordinated campaign to persuade the doctors at the prison to schedule him for a knee replacement. The man told me that he received medical treatment that would have cost him tens of thousands of dollars. With the surgery, he improved his quality of life.

Every person should start by defining success in a manner that will work for the individual. If that requires preparation for a medical strategy, then create a plan that will lead to the successful implementation of the strategy. When we find ways to make a prison journey serve our interests, we simultaneously work to restore confidence and feel better about the challenges ahead.

Step 8: Develop Personal Communication and Success Plan

People that anticipate surrendering to prison should take the crucial step of building a strong communication system and plan. If a person doesn’t know or understand how the system operates, they have a hard time planning. As a result, the people that love them, and the people they love struggle with unnecessary worry.

First, a person should understand the basics. Administrators will authorize most people in prison to communicate with people beyond prison boundaries in one of a few ways:

  • Send and receive letters through the regular postal service, provided the person adheres to specific procedures.
  • Use a modified telephone system, provided the person adheres to specific procedures.
  • Understand the modified email system, provided the person adheres to specific procedures.
  • Coordinate visits with people—provided the person and the visitor adhere to specific procedures.

Readers should note the qualifying language in the four points above. Administrators can place limitations or restrictions on people. Those restrictions or limitations may relate to the person’s conviction. For example, administrators may prohibit access to communications if the person has a specific type of crime. Also, a person may lose those privileges for violating the disciplinary code in prison.

A person can advance prospects for access to the various communication systems by preparing. For example, a person may want to type out a sheet of paper that includes the following information for all of the people on a contact list:

  • Name
  • Mailing Address
  • Phone Number
  • Email address

A day or two before surrendering, the person should print out the page and send it in the regular mail to himself, at the prison’s address. The person will also want to bring the paper with him when he surrenders. If an unsympathetic officer does not allow the person to bring the paper in with him, the person will receive the paper in the mail the following day. The person will need that information to access communication channels.

Prior to surrendering to prison, the person should help all people on the contact list understand the rules of the system. Although rules vary from time to time, administrators will limit access to each of the communication channels—other than the U.S. postal service. People can send or receive letters through the mail, provided that they can purchase postage. With regard to email, phone, and visits, limits may apply.

The more time a person spends learning about the various communication systems, the better a person will understand how communications in prison differ from communications outside of prison. Everyone in the support group should understand the system, too. Better understanding will lower vulnerabilities to restrictions.

In our ten-part course on how to succeed in prison, we offer strategic plans people can use to communicate with others.  We highly recommend that all people work through that project, which we can summarize as follows:

  1. Define success
  2. Set goals
  3. Make a commitment to your success
  4. Visualize how the strategy will influence a better life
  5. Create clear action plans
  6. Build accountability logs
  7. Stay aware of opportunities, and make the marketplace aware of progress
  8. Live authentically
  9. Celebrate incremental achievements
  10. Show appreciation and gratitude for today’s blessings

Step 9: Create Your Quadrant-Guide for Decision Making

As the penultimate step, we recommend a person develop a quadrant strategy. While climbing through 9,500 days of imprisonment, I learned the value of creating quadrant strategies. We have to make decisions from a position of strength, knowing and understanding the opportunity costs and threats that accompany every decision we make.

Financial strategists rely upon quadrants to assess how to categorize their investment decisions. Similarly, business leaders rely upon quadrants to help them understand how they’re managing their companies. If we’re going into the prison system, we’ve got to live as if we’re the CEOs of our life. We’re facing a challenge. Every decision we make will lead us closer to the best outcomes, or our decisions may send us into currents that can obliterate our prospects for success.

Good quadrants will help us engineer whether our adjustment decisions fall into the category of:

  • First Quadrant: Make decisions that offer a high prospect for success, with low levels of risk
  • Second Quadrant: Be cautious of decisions that offer a high prospect for success, with high levels of risk
  • Third Quadrant: Avoid decisions that offer a low prospect for success, with high levels of risk
  • Fourth Quadrant: Don’t make decisions that offer a low prospect for success, with low levels of risk

To the extent we categorize our decisions through a quadrant theory, we will position ourselves for higher levels of success. Our team at Prison Professors advises people to think deliberately. If each individual defines success before surrendering to prison, then the person should invest the time and energy to ensure that each decision coincides with that commitment to succeed. A quadrant theory helped members of our team, and we’re confident it can help others, too.

Step 10: Engineer Your Release Plan

Our team at Prison Professors encourages people to consider release plans long before a person surrenders to prison. As all people should, we recognize the collateral consequences of mass incarceration. Ironically, the longer our nation exposes people to the “correctional” system, the less likely people become to succeed in society.

For that reason, we encourage people to prepare a solid release plan long before they go to prison. In our book, Earning Freedom: Conquering a 45-Year Prison Term, I wrote a story about how Socrates inspired me to transform my life and begin building a release plan at the start of my journey. I hadn’t even been convicted. At the time the story inspired me to start thinking about my release, I was locked in a solitary cell at the Pierce County Jail. A jury had convicted me, but the judge hadn’t yet sentenced me. Sentencing laws required the judge to impose a term of at least 10 years, but he could have sentenced me to life.

I was 23 years old, but the predicament wrought by my previous bad decisions meant that I had to recalibrate. Circumstances forced me to contemplate the many challenges I would face ahead.

  • In what ways would serving multiple decades in prison complicate my future?
  • How would the prison system influence the way I communicated?
  • What would prospective employers think when I returned to society?
  • How would the world change while I served the sentence?
  • In what ways could I prepare myself to adjust if I didn’t understand the way the world would change?
  • Where would I get resources to start my life?
  • How much money would I need to settle in society after I got out?
  • What complications would a probation officer put on me when I got out?
  • What could I do to advance my levels of liberty, at the soonest possible time?
  • In what ways could I leverage the experience I would gain inside to bring value to others?

Asking such questions helped me to form an adjustment plan. The plan would empower me through prison, keeping me on track as the weeks turned into months, the months turned into years, and the years turned into decades.

  • What questions can you start asking now to engineer your release plan?

The sooner a person begins thinking about a release plan, the sooner that person will craft a pathway to restoring confidence.

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