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 Getting Ready The Right Way for Sentencing and Prison 

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Michael Santos

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Prepare Character Reference Letters For Judge Before Sentencing

In the previous lesson we addressed what happens after sentencing. For many, time in custody begins immediately after the sentencing hearing. For other defendants, judges extend a grace period, allowing a few weeks to pass after sentencing for the prisoners to settle affairs. In those instances, a judge sets a date and then instructs the BOP to designate an appropriate prison in accordance with classification schedules.

In this lesson we help prisoners prepare for those first days, weeks, and months.

Before offering that information, advisors at Prison Professor would like our clients to consider information about the voluntary-surrender process. Many white-collar offenders anticipate that the judge will allow them to surrender to prison voluntarily a few weeks after the sentencing date. As the surrender date approaches, those individuals sometimes ask for extensions. Although some defendants may have valid reasons for requesting the extension, others are overburdened with anxieties and want to postpone the inevitable. At Prison Professor, we urge our clients to begin serving their sentence as quickly as possible.

Individuals who are well prepared should move forward with confidence, knowing that the sooner they embark upon what looks like rough seas, the sooner they will reach smoother sailing to a better life on the other side. Peace begins to flow when an individual sets a deliberate plan and then begins to execute the plan in incremental stages. When an individual takes control of his destiny, he starts growing stronger. Like the captain who steers the bow of his ship directly into the wave to break the crash, the prisoner should take deliberate action. If he prepares himself with a solid plan, he will have the strength to charge forward. The sooner he does, the sooner anxiety becomes a distant memory. Each step forward empowers him.

Whether an individual intends to request additional time after sentencing before reporting to prison, we urge him to prepare himself so that he is ready for prison on the day of sentencing—because no one knows for sure what the judge will order. In any event, before that first day in confinement, a prospective prisoner may be wise to take precautions. At Prison Professor, we offer the following suggestions that clients may consider.

Fears and Anxieties:

We encourage our clients to work toward getting their fears and anxieties under control. It’s understandable that the thought of confinement can derail an individual. Learning that a prison sentence possibly awaits leads many into sleepless nights, binge drinking or substance abuse and domestic problems. Thriving through prison, however, requires a methodical plan. Many people find that the fear and anxiety of prison was far worse than prison itself. Preparation begins with work to understand everything to come. Confidence in an ability to master the system will grow in direct proportion to that understanding.

At Prison Professor we do not underestimate the challenges of confinement. Indeed, we know that those challenges can have lasting influences on an individual’s life and on the family. At the same time, we’re absolutely confident that anyone who adheres to the lessons we teach will make it through prison confidently. Those with well-laid plans return to society much stronger emotionally and intellectually than they felt while proceeding through the judicial proceedings. Our lessons restore confidence. Confidence leads to a plan for resilience.

Anxieties about Violence:

Some clients who retain our consultants at Prison Professor express anxieties about their exposure to violence while incarcerated. We empathize with those concerns. Although we cannot eliminate challenges, we teach strategies to minimize an individual’s exposure to violence. Violence can erupt in any environment where tensions run high. When individuals serve time, the decisions they make will influence their level of vulnerability to violence. In our subsequent lessons, we teach strategies that will minimize an individual’s exposure to violence, regardless of where authorities choose to confine him.

Our advisors at Prison Professor experienced institutions of every security level. They teach effective strategies for making the most of confinement. As Maslow taught, individuals need to position themselves for safety before they can make the best use of resources around them.


We advise our clients to collaborate with loved ones on preparations for the challenges ahead. Those discussions should begin long before the sentencing date. Each client should understand that confinement makes discussions and planning infinitely more difficult. Rules that limit access to telephones, mail, and visiting obstruct the possibility for substantive discussions. Further, while in prison, the individual will lose all expectations for privacy. For those reasons, the family must come together, the sooner the better, with a plan to triumph over the challenges wrought by confinement.

We sometimes encounter clients who find it difficult to communicate with family about the challenges ahead. Rather than involving those who are closest to them, they choose to wait, anticipating that the problems will somehow work themselves out. It’s understandable. Some people find it impossible to contemplate imprisonment. We guide them with the following self-directed exercises. This introspective work may assist them in clarifying their thoughts. We recommend that our clients respond to the following questions, and keep answers private:

  • What crimes do prosecutors accuse me of committing?
  • If judicial proceedings result in a finding of guilt, what type of sentencing range does my attorney suggest I could receive?
  • What level of commitment do I make to protect my family, regardless of the outcome of my proceedings?
  • In what ways would delaying discussions with family demonstrate my commitment to protect them?
  • In what ways would speaking honestly with family immediately, and through every stage of the proceeding, prepare them for challenges ahead?
  • In retrospect, what decisions led to the challenges that I’m now facing?
  • What do I know now that I didn’t know when I made decisions that led me into this predicament?
  • How can I explain decisions that I made to the people I love most?
  • What level of confidence do I have in my ability to cope with the response that I anticipate from them?
  • What decisions can I make now to ensure that I return to my family stronger at the outcome of these proceedings?

Those questions may not be appropriate for everyone. But exercises in introspection can guide our strategy for overcoming difficult, challenging times.

  • What questions are you asking yourself now?
  • How will your responses to those questions guide you through turbulent times?

Family Budget:

Ensure that the family has a financial-resource plan to cover costs of living without the individual’s income. Our consultants at Prison Professor can provide insight on strategies that some prisoners have used to earn an income during the incarceration period. Yet the vast majority of people in prison will not have sufficient time to create an income strategy that could offer meaningful support to the family. Accordingly, individuals should have a solid plan in place to sustain the family. Those plans should be measurable. They should offer accountability metrics that track performance throughout the journey inside. If financial concerns are an issue, both spouses should participate in this budget exercise. They should establish a plan to discuss and review progress at specific times throughout the journey. We will cover such joint accountability metrics in future lessons.

Business Affairs:

If our client has business interests, we urge him to put a plan in place to manage those affairs. Rules are well defined in prison. An individual who understands those rules well empowers himself. He will know precisely what he can and what he cannot do. Further, an individual who understands the rules will be able to make calculated, rational decisions about how involved he should be in an ongoing business. Other areas of our website offer more insight on the subject of operating businesses while incarcerated. Those lessons profile individuals who continued to have a role in leading their business interests while inside. They succeeded because they had a plan in place. The best-laid plans are those that an individual makes prior to the sentencing date.

If our client has business interests, we urge him to put a plan in place to manage those affairs. Rules are well defined in prison. An individual who understands those rules well empowers himself. He will know precisely what he can and what he cannot do. Further, an individual who understands the rules will be able to make calculated, rational decisions about how involved he should be in an ongoing business. Other areas of our website offer more insight on the subject of operating businesses while incarcerated. Those lessons profile individuals who continued to have a role in leading their business interests while inside. They succeeded because they had a plan in place. The best-laid plans are those that an individual makes prior to the sentencing date.


Individuals who are on precarious financial footing should consider liquidating assets that they cannot easily maintain during confinement. BOP rules will make it difficult—though not impossible—to oversee business affairs. If an individual doesn’t have a solid strategy in place to maintain assets, we strongly suggest that the individual consider liquidating assets prior to the sentencing date. It is much more difficult to liquidate assets while under the duress of confinement. This advice applies to items that include vehicles, art collections, wine collections, jewelry, and even real estate. If the individual doesn’t have a solid plan to maintain the assets, and the financial system in place to oversee and protect them, converting the assets to cash or cash equivalents may be wise. Then, the individual could set a plan in place to distribute that cash over time, preserving some to reboot his life after release.

Budget for the Prisoner:

The individual should have a budget to carry him through the duration of his sentence. The budget for the prisoner should not jeopardize family stability at home. Conditions of confinement become infinitely worse when loved ones are left without adequate financial resources. This exercise of establishing budgets is consistent with a commitment to establishing a deliberate plan to succeed, regardless of external forces. If resources do not provide for a budget that would last for the duration of the sentence, prospects for changing that scenario are infinitely greater prior to the sentencing date than they would be while incarcerated.

Power of Attorney:

While in custody, issues may come up that require the prisoner’s immediate action. Unfortunately, the Bureau of Prisons does not respond well to “urgent” matters. Further, there may be occasions where the prisoner wants to handle a business matter without involving the BOP. To prepare for such instances, an individual may consider issuing a Power of Attorney to a family member or a trusted advisor. That document will authorize the person who holds the Power of Attorney to sign on the individual’s behalf. Depending on the length of confinement, issues may surface where having such a resource would prove valuable.


Prior to the sentencing date, individuals should notify all friends with whom they would like to maintain contact. The same introspective questioning that we suggested to guide discussions with family may prove useful in discussing the predicament with friends. Relationships with the outside world can prove enormously helpful during the imprisonment phase. A proactive approach to maintaining those relationships may minimize the possibility of disappointment from friends who fade away during the sentence. A “proactive” approach would include keeping friends apprised of what to expect. Provide them with guidance on how to maintain communications. If visits are a possibility, instruct friends on the procedures that make visits possible.

  • After sentencing, visit to learn the registration number authorities have assigned.
  • Under the “Inmates” tab, read about visiting procedures.
  • Under the “Resources” tab, click on “Forms” and read about Visitor Information.
    • All visitors must complete that form and send them to the prison.
  • Help friends complete the form so they will be ready to submit at the appropriate time.
  • Instruct friends to mail the form directly to the assigned counselor in the prison after the individual is admitted; authorities will not accept visiting forms from a prisoner.


Federal prisons have libraries that include many westerns and romance novels. If an individual has an interest in specific books, then the individual may consider making a list of books prior to surrendering. The individual may want to circulate that list to family and friends. The individual may want to work with them in preparing a “book plan,” where family and friends will send specific books at specific times. This strategy can serve the dual purpose of helping the individual pass through the time while keeping those who send the books involved in the journey. At Prison Professor, we encourage our clients to get in the habit of writing simple book reports for every book read during the journey. Those book reports should include the following information:

  • Title: Insert book’s title
  • Author: Insert book’s author
  • Date Read: Insert date individual finished reading the book.
  • Why I chose to read this book: Insert information on what interested the individual about the book.
  • What I learned from reading this book: Insert information on what the individual learned from reading the book.
  • How reading this book will contribute to my success upon release: Information on how reading this book relates to the individual’s future.

This methodical reading plan has helped many of our clients through the journey. They use it upon release, too, to show others the deliberate strategy that carried them through prison. The strategy may show that an individual wants others to judge him by the way that he responded to struggle rather than the decisions that led him into struggle.


We encourage individuals to have a full medical and dental checkup prior to the time they expect to begin serving time in custody. The Bureau of Prisons markets the bureaucracy as offering best-in-class medical treatment. At Prison Professor, our experiences with BOP healthcare left us with a different perception. If by best-in-class healthcare, the BOP compares itself with healthcare offered in state prisons, the statement may be accurate. Yet since the Supreme Court has ruled that numerous state prison systems failed to provide healthcare to inmates at a level guaranteed by the Constitution, such a barometer for measuring excellence would be quite low.

In any event, individuals who anticipate serving time in prison would be wise to visit a physician for a full checkup. We suggest asking the physician for immunizations that would be appropriate before going on safari, or traveling into third-world countries for prolonged periods of time. Individuals should get every type of appropriate medication that would protect against viruses or illnesses.

Prisons confine a transient population of individuals, and statistics show that they are not the healthiest lot. Indeed, illicit, intravenous drug use and tattoos have made many people in prison susceptible to infectious diseases that could be contagious. To the extent possible, people who anticipate serving time inside should speak with a physician and take precautious. The physicians may suggest an individual treatment plan that could protect an inmate’s health in an environment that crowds many people into confined spaces.

If the individual has documentation from a medical doctor that shows health challenges such as:

  • Chronic suffering from back pain
  • Orthopedic ailments
  • Arthritis
  • Diabetes

or other medical conditions, the individual may succeed in persuading prison guards to authorize him for a lower-bunk pass, preferred housing quarters, or a light-duty job assignment. If the individual has verifiable medical needs, for which he requires ongoing treatment, the individual should ask his physician to document the illness and treatment plan prior to the sentencing date in order to ensure he has the documentation prior to imprisonment.

At Prison Professor, we caution our clients to recognize this request for a treatment plan from a physician is only a first step in the process. It’s a step we advise because we understand the challenge of obtaining preventative medicine while inside. Obtaining that treatment plan from a board-certified physician may serve to document the record that a prisoner will need if he finds himself confined inside of an institution that fails to provide adequate healthcare.

Unfortunately, obtaining adequate healthcare treatment is one of the most common complaints of people serving time. We advise our clients to anticipate that they may need the administrative remedy system to resolve their health issues. An individual can strengthen chances of prevailing through that quasi-legal system if he prepares himself in two ways prior to surrendering:

  • Obtains written documentation of a treatment plan from a board-certified physician prior to imprisonment, and
  • Reading and understanding the Program Statements and Policies that govern BOP Health Services. Some of those Program Statements Follow:
    • Number 6090.03: Health Information Management
    • Number 6010.05: Health Services Administration
    • Number 6013.01: Health Services Quality Improvement
    • Number 6190.04: Infectious Disease Management
    • Number 6270.01: Medical Designations and Referral Services for Federal Prisoners
    • Number 6541.02: Over-the-Counter Medications
    • Number 6031.04: Patient Care
    • Read and review the Bureau of Prisons’ National Formulary, available at: National Formulary:

Obviously, reading and mastering the Program Statements we mention above will require an investment of several hours. Our consultants at Prison Professor work with clients who anticipate that prolonged periods of incarceration may follow. We encourage clients who express concerns about needs for ongoing medical treatment to understand those policies before they surrender. The knowledge they obtain from that investment of time will empower clients when they’re in the moment of receiving what they may perceive as “inadequate attention” to their healthcare needs.

If the individual’s physician prescribes medication for the individual, the individual should bring a limited amount of that prescription with him to the sentencing hearing. If the judge grants him time to get his affairs in order before he surrenders to prison, he should bring the prescription when he reports to prison—provided he has the doctor’s order. He may face some resistance from guards, but the doctor’s order along with the detailed medical records will result in an authority figure making the decision.

As the cliché holds, the squeaky wheel gets the grease. If a BOP staff member recognizes that the patient has knowledge about internal policies, the staff member will not be so quick to show deliberate indifference to an inmate’s request for medical attention. Further, if the staff member continues to provide inadequate medical attention, the client may argue from a stronger position when he seeks redress through the administrative remedy procedure.


In addition to seeing a physician, an individual should also see a dentist and obtain a complete dental exam. If the dentist or oral surgeon recommends treatment, our consultants at Prison Professor urge the client to have that dental work done prior to imprisonment. In federal prison, requests for dental treatment frequently result in pulled teeth. Authorities reason that by pulling teeth, they will not have to confront the problem again. Yet specific procedures are supposed to govern whether authorities can pull teeth, and individuals should know those procedures that administrators are supposed to follow. In addition to the general information we provide about healthcare, for dental work, we encourage our clients to read and understand Program Statement 6400.02, which covers Dental Services in the Federal Bureau of Prisons. That way, in the event that they have a toothache, and the dentist wants to pull the tooth, the individual will know whether he has a right to dental treatment that will save the tooth.

Eye Care:

While incarcerated, well-educated individuals will likely read more than at any time in their life. As such, their vision is extremely important. At Prison Professor, we urge our clients to visit an eye doctor long before the incarceration period begins. While inside, years may pass before the inmate has access to an ophthalmologist. Contact lenses will only be permitted under certain medical-related conditions. To avoid complications, we urge our clients to have their eyes checked prior to surrendering. If they need prescription eyeglasses, or even reading glasses, we urge them to bring two pairs when they surrender. The individual should choose sturdy rather than fashionable eyeglasses, and they should bring a case for the eyeglasses. When eyeglass frames break in prison, the wait may be long to receive a replacement pair.


Theoretically, the prison will provide the prisoner with everything he needs to survive. Each institution will provide three meals each day; clothing; basic hygiene items. The government-issue rations, however, do not compare favorably with American standards. Instead of toothpaste, for example, those on government ration will receive some type of powder. Razors will be single-blade and cut the skin while shaving. Clothing issues will not be sufficient for exercise.

Just as financial resources ease life in society, money can improve the quality of life inside. The problem is that few opportunities exist for individual to earn the resources necessary to cover the costs of living in prison. Subsequent lessons will discuss those income opportunities. At Prison Professor we consider state of mind and attitude to be the essential elixirs for a positive experience during imprisonment. Though if an individual also has access to financial resources, the adjustment inside may be easier.

Each federal prison will operate a commissary. That commissary will sell food, clothing, hygiene items, and other products that the prisoner will appreciate. The federal prison system imposes a spending limit that fluctuates from time to time, restricting the amount of money that an individual can spend each month in the commissary. The current spending limit is less than $350 per month, though administrators alternate that spending limit from time to time. Expenditures on telephone access, email access, or stamps do not count against the spending limit. With the cost of postage, telephone, and basic hygiene supplies, inmates should expect to spend a minimum of $100 per month. Though well-healed prisoners will spend $1,000 per month or more to improve their quality of life inside. A newly-arriving prisoner can ease his start significantly if he can budget between $500 and $800 to purchase clothing, hygiene, a radio, and food.

The Bureau of Prisons does not encourage inmates to surrender to prison with money. Instead, it offers two electronic options that include Western Union and MoneyGram. In the alternative, individuals can send funds through the mail to the BOP’s central location in Iowa, using a US Postal Money Order. Individuals should not send funds to the institution. If sending funds through the mail, make sure the envelope includes a return address. Send the U.S. Postal Money Order to the following address:

  • Federal Bureau of Prisons
  • Individual’s name
  • Individual’s eight-digit BOP registration number
  • O. Box 474701
  • Des Moines, Iowa 50947-0001

If an individual provides funds to a trusted family member, the family member may send funds electronically as soon as the individual is checked into the prison. By sending funds electronically, the individual will receive the funds within four hours. An individual may bring a few hundred dollars, or a US Postal Money Order made out to his name when he surrenders; some institutions will accept the resources and credit them to the inmate’s account immediately, others may not. At Prison Professor, we encourage the use of electronic deposits, at least for the first deposit. After the individual settles in, he may choose to advise his loved ones to send funds to the Iowa P.O. Box for deposits.

Phone Numbers, addresses, and email:

Once an individual is admitted into the prison, he will have access to the telephone and email system. To use those services in prison, however, the individual must first submit the names and numbers of the people with whom he intends to communicate. If an individual doesn’t have that information, he will not be able to call anyone. At Prison Professor, we advise our clients to prepare in the following ways, prior to sentencing if possible:

  • Type out a complete list of the initial people with whom he would like to communicate.
  • The list should include name, address, email address, and phone number.
  • The individual should use the U.S. Postal Service to mail the list to himself at the prison address; he should time the mailing so that it arrives on the same day that he intends to surrender, or the day after. It may be wise for the individual to copy this document, and send multiple envelopes. That way the individual will increase his chances of receiving the information when he arrives that is crucial to his initial adjustment.
  • The individual should also bring the list with him, at sentencing or when he surrenders.
    • The admitting officer may or may not allow the individual to carry the list with him.
    • Since the individual will be allowed to bring legal documents with him, the individual should handwrite a few important numbers on the legal documents so that he is ready to communicate with others when given the opportunity.

Personal Belongings:

  • Wedding ring: Policies provide that an individual who surrenders to prison may bring a wedding ring, provided that the ring does not have any stones attached to it. Theoretically, the ring is not supposed to have a value in excess of $100. Yet as long as the band is simple, preferably without engravings, no one is going to question the value. That policy has been in place since at least 1987, and the prices have not been adjusted for inflation.
  • Religious medal: An inmate may wear a religious medal with him when he surrenders. Again, the medal must have a value of less than $100.
  • Book of Worship: An individual may bring a prayer book when he surrenders, including a Bible or other type of religious book.
  • Legal Documents: An individual may bring a simple envelope with legal documents; those documents cannot include the PSI, however. Rules prohibit individuals in federal prison from having a PSI in their possession.
  • Watches and clothing: The rules do not provide for individuals to bring watches or clothing items with them when they surrender. That said, some guards who admit the individual may allow the individual to enter the prison with the following items:
  • Watch: inexpensive, digital model. Federal prisons sell Timex Ironman watches.
  • Sneakers: May wear inexpensive, white sneakers, no logos preferred.
  • Sweats: Gray, no logos
    • It’s unlikely that guards will allow the individual to enter the institution with watches or clothing items. But if an individual wants to try, we encourage the individual to purchase items that he would feel comfortable donating to the institution in the likely event that the guard will not authorize those items to come into the institution.
  • Become a minimalist. We encourage individuals to purchase all personal belongings through the prison store, known as the commissary. That is the surest way to minimize complications.


  • When reflecting on decisions you’ve made over the past decade, what insight that you have now would’ve prompted different decisions?
  • In what ways could the experiences you’ve had over the past decade bring value to the life of someone else who is embarking upon the same journey?
  • What value would you find in learning from others who’ve gone through the journey that you’re about to embark upon?
  • What would you want to learn from them?
  • Describe how the journey ahead will influence your life after proceedings with the criminal justice system conclude.

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