Values and Goals 

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Section I

Preparing for Success after Prison

Welcome to our course: Preparing for Success after Prison. 

As readers will find in this course, it’s never too early, and it’s never too late to begin preparing for success after prison.


Lots of reasons, including recidivism rates.

No one believes that they will return to prison after release. Unfortunately, statistics show that many people going into the system face enormous hurdles when they get out. From the time of an initial arrest, a person’s life changes in unanticipated ways:

  • They must interact with criminal defense lawyers, prosecutors, and a judicial system they don’t understand.
  • If a prison term follows, people get separated from those they love. Friends and family move on, which causes anxiety.
  • While living in the system, constant challenges can complicate an adjustment—regardless of security level.
  • Upon release, people face challenges finding housing, securing credit, or keeping up with an ever-changing society.

On the other hand, some people leave prison and thrive. Take the case of Weldon Long. His struggles with addiction influenced his behavior as a young man. Weldon participated in armed robberies that led to three separate prison terms. During his first two terms, he adjusted to the culture of confinement. Decisions inside led to further problems outside. After his third conviction, Weldon decided to transform his life. Now he leads a company that provides sales training to major corporations, such as Wells Fargo, Federal Express, Home Depot, and others.

What made the difference?

During his third term, Weldon decided he didn’t want to live a criminal lifestyle any longer. He chose to prepare for success after prison. Regardless of what went on inside the penitentiary, he could always work toward improving himself by:

  • Enhancing his vocabulary,
  • Improving his writing skills,
  • Becoming a better verbal communicator,
  • Evolving his critical-thinking skills,
  • Developing a self-directed work ethic.

Like many other people in prison, Weldon eventually learned that regardless of what went on around him, he bore the responsibility to prepare for success upon release.

Many people in prison believe that while living inside, they should focus on the culture of confinement and forget about the world outside. People who succeed upon release understand that an urgency exists. The sooner they start sowing seeds for success, the more effective they become at opening opportunities. 

Our course on Preparing for Success after Prison urges participants to pursue a self-directed strategy. We offer the course in three sections:

Section 1: 

Lessons 1 through 5 offer an introduction, showing the power that comes from leading a values-based, goal-oriented adjustment.

Section 2:

Lessons 6 through 15 provides guidance on how any person in prison can use this strategy to begin sowing seeds for a better outcome.

Section 3: 

Lessons 16 through 30 offer stand-alone lessons on personal development.

Each lesson should require about one hour to compete. Participants who work through the 30-hour course should engineer a personal release plan that will allow them to:

  • Define the best possible outcome,
  • Create a release plan that will lead to success,
  • Put priorities in place,
  • Develop their tools, tactics, and resources,
  • Create personal accountability metrics, and
  • Motivate them to work relentlessly at executing the plan.

Our entire team at Prison Professors believes that anyone can work toward becoming extraordinary and compelling. It all starts with a personal release plan. Iterate the plan over time and document the incremental steps necessary to prepare for success. 

For people in federal prison who want ongoing support, please send us a Corrlinks invite to get our newsletters. 

We believe in you.

Lesson 1: Values and Goals

Define Success

Annotations: Values and Goals

Regardless of what stage in the journey we’re in, we can begin sowing seeds for success by looking back and looking forward. In this introductory lesson, we’ll get started on what it means to define values and goals—with a reflection on thoughts we could consider (or should have considered) before sentencing.

My name is Michael Santos and I’m the founder of Prison Professors. I’m grateful to introduce our series on Preparing for Success after Prison. 

For full disclosure, I’m a person who served a lengthy prison term. Since concluding my sentence, in 2013, I’ve advocated for reforms that would lead to more incentives for people in prison. As participants in this course will find, I’ll never ask anyone to do anything I didn’t do while going through 9,500 days in prison, and that I’m not still doing today. 

Leaders taught me lessons on how to prepare for success upon release. Since those lessons worked for me, others may want to learn from them.

Regardless of what stage of the journey a person may be in, we know that it’s never too early and it’s never too late to begin sowing seeds for success. At any time, we can look back on the decisions we made. If we introspect, we can see how our early decisions led to where we are today.

Likewise, if we project into how we want to live in one year, five years, or ten years, we can reverse engineer a plan. That plan can lead us to the success we want to become.

Course design / Time Requirements / Resources:

A participant should complete each lesson in 50 to 90 minutes using this self-contained workbook. The time variable depends on whether participants watch the optional DVD video profiles or engage in interactive exercises—we make the video files optional because not all institutions have the capacity to offer such resources.

With each lesson, participants will have opportunities to show how they’re engineering a pathway to success. 


Through our Preparing for Success after Prison series, participants will develop skills. Those skills contribute to each participant’s success—regardless of the stage in the journey or place of confinement. For example, the lessons will help people if they’re:

  • Contemplating their response to a criminal charge,
  • Preparing before sentencing,
  • Engineering an adjustment strategy that leads to the best outcomes,
  • Preparing for a career after release.

Lessons in the Preparing for Success after Prison series assist people who want to help themselves. And the self-contained lesson plan includes everything a person needs to complete the personal-development exercises. Those exercises will lead to:

  • Expanding a vocabulary,
  • Improving writing skills,
  • Developing reading skills,
  • More confidence when communicating verbally,
  • Critical thinking skills,
  • Commitment to self-directed learning, and
  • Advanced networking skills to find mentors.

Personal Exercises:

We’re purposely writing this course at a basic level, using short sentences and simple analogies. Mostly, we write from the plural voice with gender-neutral pronouns. We will occasionally use “he” or “she” because we want to be inclusive. The lessons apply to all justice-impacted people, regardless of age, ethnicity, or gender. 

We minimize labels such as “inmate,” “convict,” or “prisoner” because we want participants to identify as people or citizens of the broader community. Our entire team at Prison Professors strives to help people emerge from prison with their dignity intact and with opportunities to thrive as the individual defines “thriving” or “succeeding.”

Note on Vocabulary Building:

The end of this booklet includes a lexicon. That’s another word for dictionary. If we highlight a word in bold italics, we cite that word in the back of the book. The back-of-the-booklet lexicon includes a definition. We encourage participants to learn any words they do not know as part of a self-directed vocabulary-building exercise. Participants who make a commitment will not need a teacher, a classroom, a video player, or any resource other than this simple workbook (or collection of printed lesson plans) to build a more robust vocabulary.

Note on Developing Writing Skills: 

Each lesson includes a series of open-ended questions. Participants may write as little or as much as they would like. Questions do not have a single right or wrong answer. Instead, each answer should align with how a person thinks. And people think differently. If a person chooses to develop better writing skills, that person will become more valuable in the marketplace. People can develop better writing skills and thinking skills if they use this self-directed learning strategy.

Note on DVD Supplement: 

Each lesson includes an optional DVD video. We burned captions into the bottom of each video. Participants may read the captions while listening to enhance their reading skills. The DVDs include interviews with justice-impacted men and women from different backgrounds. Those people either built successful careers after their release from prison or triumphed over other adversity. The videos also include ideas that justice-impacted people can use to prepare for income-generating opportunities upon release. When we listen to successful people share their stories, we find clues or takeaways we can use to become more successful.

Section one covers five lessons:

  • Defining Success with Values and Goals,
  • Attitude and Aspiration,
  • Action and Accountability,
  • Awareness and Authenticity,
  • Achievement and Appreciation.

As a virtual instructor, let me start by sharing the backstory. To earn trust, participants will learn that I never ask anyone to do anything I did not do while going through a personal journey that included multiple decades in prison.

I’d like to earn your trust.

History of the Course:

Our Preparing for Success after Prison series is part of a larger project, a lifelong commitment to advocating for justice-impacted people. To succeed, I rely upon the same lessons I’m offering in this course. To advocate effectively, we need to build coalitions with many moving parts, including:

  • Legislators that influence laws,
  • Administrators that influence policies,
  • Justice-impacted people that go through the system,
  • University scholars who assess the effectiveness of our programs,
  • Business owners that may work with justice-impacted people,
  • Financial institutions that influence collateral consequences for justice-impacted people,
  • Community organizations that welcome justice-impacted people into society, and
  • Citizens that vote.

As this course teaches, succeeding as an advocate requires us to influence authority figures. We must begin with a plan. To influence authority figures, we must develop more skill at turning letters into words, words into sentences, sentences into paragraphs, and paragraphs into persuasive arguments. We learned that lesson in advocacy from authority figures, such as Frederick Douglass.

Frederick Douglas and the Power of Advocacy:

Some participants may know the story of Frederick Douglass, who began his life as an enslaved person. That struggle brought enormous adversity. In time, an opportunity opened for him to escape to freedom. Rather than moving on to enjoy his liberty, Mr. Douglass devoted his life to advocacy, working tirelessly as a force for the abolition of slavery.

To succeed in getting the outcome he wanted, Frederick Douglass understood that he would need to develop new skills:

  • He had to learn how to read.
  • He had to learn how to write. 
  • He had to learn how to speak persuasively.
  • He had to learn how to build a coalition of influential people.
  • He had to work with those influential people to change laws that would lead to the abolition of slavery.

The story of Frederick Douglass gives us an example of excellence. Despite being born into slavery, he adhered to a values-based, goal-oriented strategy to live for good. Millions of other people benefited. Knowing it would be a long walk to freedom, as another great advocate advised us, Frederick Douglas advanced the cause by turning words into sentences and sentences into paragraphs. 

To use his life’s story as a tool that would persuade more people to believe in his vision, he authored three autobiographies:

  • Narrative of the Life of Frederick Douglass, an American Slave,
  • My Bondage and My Freedom, and
  • Life and Times of Frederick Douglass

By writing his life story, Frederick Douglass developed the power to influence people he would never meet. Readers began to see a different perspective as they read about his experiences and the resilience of his life. They invited him to participate in public forums, where he would deliver orations and respond to questions from the audience. Through his story, he changed the minds of adversaries.

Some people criticized Frederick Douglass because he spent time with people who supported slavery, including those who enslaved others. Those critics wanted to know why he would converse with anyone supporting slavery. Mr. Douglass said he did not need to convert people who knew the evil of slavery; he lived by the motto: “I would unite with anybody to do right and with nobody to do wrong.”

By changing minds, Frederick Douglass influenced how people voted. He persuaded people to see that slavery was wrong and convinced them to elect candidates who would vote to abolish slavery.

Take Ten Minutes (1-1): 

Write responses to the following three questions in approximately ten minutes. If participating in a class setting, discuss verbally.

1-1: What takeaways can you gather from this abbreviated lesson on Frederick Douglass?

1-2: In what ways can this brief synopsis on Frederick Douglass influence a strategy you create to prepare before you face an authority figure that will judge you?

1-3: In what ways would you say that slavery influenced Frederick Douglass’ understanding of the world?

Personal Story:

Unfortunately, I didn’t begin to learn from leaders like Frederick Douglass until after prosecutors convinced members of a grand jury to indict me. DEA agents arrested me on August 11, 1987, when I was 23. I’d never been incarcerated before that arrest and didn’t know what to expect. At that stage in my life, I only wanted liberty.

With that mindset, I willingly listened to people around me who told me what I wanted to hear rather than what I needed to hear. Then, I made more bad decisions.

Since my charges carried a potential life sentence, I spent most of my pre-trial detention in solitary confinement. Because of that time in solitary, I didn’t learn much about how the criminal justice system operated. Without knowledge of the legal system, I left myself vulnerable to the messages other people in the detention center tried to convey. Those people gave me a variety of messages:

  • There was a big difference between an indictment and a conviction.
  • The best way to serve time would be to forget about the world outside and focus on my time inside.
  • The government only wins cases because most people plead guilty; prosecutors rarely prove cases when people go to trial. 

By listening to viewpoints of questionable value, I made a series of catastrophic decisions. Following the trial, members of the jury convicted me of every count. My choices exposed me to a harsher sentence than I would have received if I had acted differently. Following the first trial, prosecutors brought new charges of perjury against me. 

Take Ten Minutes (1-2):

Write responses to the following questions in approximately ten minutes. If participating in a class setting, discuss verbally.

1-4: In what ways would you say the author’s preparation before sentencing differed from the leadership of Frederick Douglass?

1-5: In what ways would you say the author’s conviction influence possibilities for him to become an advocate?

1-6: How would you predict that authority figures in society would respond to the author’s conviction?


Looking back, I see how my lack of preparation before sentencing hurt me. Instead of responding deliberately, with an intentional strategy during a pivotal moment, I abdicated all responsibility to prepare. 

I effectively gave up by allowing myself to succumb to guidance from others. Rather than being intentional about my decisions, I hoped that someone else could solve problems spawned by my previous decisions.

Frederick Douglas took a different approach. He didn’t only think about what he wanted or what would benefit his life. He thought about society and figured out ways he could influence the making of a better community for all. Then, he embarked upon a methodical, deliberate plan. To abolish slavery, he understood that he would have to:

  • Define success as the abolition of slavery,
  • Put a plan together that would advance prospects of abolishing slavery,
  • Put priorities in place, 
  • Execute the plan, and
  • Hold himself accountable.

Preparing for success at any phase in life requires that we begin by defining success. Then, we must set clear and SMART goals that align with our definition of success. If we value success, we need to take the incremental steps that will lead to success.

Whether we like it or not, we must live in the world as it exists and not as we want it to be.

Frederick Douglass understood that slavery existed. He couldn’t wish it out of existence. Instead, he had to take a series of systematic steps that moved closer to success as he wanted to experience success—living in a world that did not allow anyone to enslave another person. He had already solved his problem by escaping from slavery. But he also wanted to solve problems that were far bigger than his own.

I didn’t have that presence of mind when I began serving my sentence. I simply wanted to get out of detention and avoid prison. I didn’t think about anything other than what I wanted. 

That mindset would not work out so well for me. 

I would have been far better off thinking about stakeholders in the system. As Zig Zigler, an influential sales leader, is famous for having said:

“If we can help others get what they want, we can get everything we want.”

I didn’t learn those lessons until long after a judge sentenced me. Reflecting on those months before sentencing, I see that I made many mistakes by not thinking about stakeholders. Had I considered the questions below, I would have used these strategies to prepare before sentencing.

Take Ten Minutes (1-3):

Write responses to the following questions in approximately ten minutes. If participating in a class setting, discuss verbally.

1-7: What motivates a prosecutor?

1-8: What motivates a judge?

1-9: What motivates the people who will influence prospects for liberty going forward?

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