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 4-Success after Prison 

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Michael Santos

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To succeed after prison, start by engineering a plan that will bring more people into your life. Give them the reasons to invest in you and your dreams.

Carole: Nurturing Love in Prison

Our decisions in prison influence the opportunities that open for us. 

When I began serving my sentence, many people offered their thoughts on how to serve a sentence. They suggested that the best way to fill time would be to forget about the world outside and focus on time inside.

If a person chooses to focus on time inside, the person must also accept the consequences. He may not like the result. As the person focuses on fitting in with the prison expectations, he may find fewer opportunities to succeed when he gets out. Statistics show that the more time we spend in corrections, the more likely we struggle with underemployment, unemployment, or even homelessness. Those problems can lead to further problems with the law and a return trip to prison.

Instead of distancing myself from society, I chose to build bridges and connect. That strategy broadened my support network. It led to correspondence with Carole, a friendship, and then to our wedding inside a federal prison’s visiting room on June 24, 2003, as I completed my 16th year. We’d have to spend ten years apart before we could live together.

Carole became my liaison to the world. I’d write by hand and send my manuscripts to her. She’d interact with publishers or work to bring my projects to life. If I hadn’t sown seeds early in my journey, Carole would never have begun a romantic relationship with me. She didn’t only become the love of my life, but she also provided further evidence that if we pursue a deliberate strategy, we can transcend the challenges of confinement:

  • Start by defining success as the best possible outcome,
  • Create a plan,
  • Set priorities that will advance the plan in incremental steps,
  • Develop tools, tactics, and resources that promote each phase of the plan, and
  • Execute the plan every day.

Together, Carole and I worked to create a quasi-business, despite our unconventional life.

  • My writing generated revenues that supported my wife.
  • We paid taxes.
  • Revenues from my writing projects allowed Carole to work toward a nursing degree.

All our efforts would relate to a strategic plan. The plan would allow Carole to live a sustainable life while I prepared for a meaningful career upon release. She relocated to live in the community where I served my sentence. When authorities transferred me to another prison, Carole would relocate with me. We visited every day that the rules would authorize.

Besides writing books under my name, I began ghostwriting books for other people to advance our projects. Every decision I made in prison began with one question:

  • Will this decision lead to success upon release?

That strategy empowered me through the journey.

  • It dictated the books that I read while I served the sentence.
  • It dictated the people with whom I associated.
  • It dictated the jobs I tried to secure in prison.
  • It dictated my efforts to persuade counselors to assign me to a bunk that would minimize exposure to volatility.

In later chapters, readers will see how that strategy influenced higher income opportunities upon release and higher levels of liberty. Higher levels of income and freedom created new opportunities. They allowed me to build an asset portfolio that would contribute to my financial security.

The adjustment in prison led to more than $1 million in appreciating assets and more than $500,000 in equity within 28 months of release. People striving for a better life after prison may modify this strategy to suit their definition of success. They can begin by asking Socratic questions throughout the journey and projecting how today’s decisions will influence their desired results.

More than anything, I wanted to emerge successfully. Daily decisions related to what I wanted to achieve in months, years, and decades ahead. When reading a book, for example, I’d read with a purpose. When I finished reading the book, I’d write a report in accordance with the following format:

  • Date I read the book:
  • Why did I choose to read this book?
  • What did I learn from reading this book?
  • How will this book contribute to my prospects for success upon release?

Adhering to that strategy made me more selective with what I read. Reading takes time, and I wanted to get the most value from the time I invested in personal development. Then, I worked to harness the value and create an asset—the book report. Later, I anticipated I could use the book report as validation, showing others how I used time in prison to prepare for success. Every decision directly connected to the success I felt determined to become.

Many opportunity costs and risks accompany our decisions. Since I knew that many people in prison placed a high value on where they positioned their seats in a television viewing area or whether they had the authority to change a channel, I avoided television rooms.

Every decision began with a question that related to the life I wanted to lead when authorities released me:

  • If I choose to watch television, will that decision advance or hinder my prospects for success upon release?
  • If I play organized sports, will that decision advance or hinder my chances for success upon release?
  • If I play table games, will that decision advance or hinder my prospects for success upon release?
  • If I associate with one person or another, will that decision promote or hinder my opportunities for success upon release?
  • If I participate in this program, will that decision advance or hinder my prospects for success upon release?
  • If I express my opinion around others, will that decision advance or hinder my prospects for success upon release?

Each question had a purpose.

Rather than making decisions that would ease my journey, enhance my reputation in prison, or advance my standing with other people, I considered the avatars. I didn’t know the avatars, but each of them existed in my mind, and they felt lifelike.

I considered the people with whom I wanted to associate in the future. Then I contemplated whether my decisions would show good judgment. How would my decision influence the possibility of support from the avatars I wanted in my life?

If my decisions followed that “principled” pathway, I built confidence. I didn’t feel the pain of multiple decades in prison when I empowered myself. Instead, each decision represented a new investment in personal development that would lead to higher levels of success.

I wasn’t perfect, of course. I made some bad decisions along the way. Yet, adhering to the strategy always helped me get back on track.

  • In what ways could this strategy help you?

Final Preparations before Release from Prison:

As I advanced through my final years of imprisonment, I could reflect on the totality of my journey. Leaders taught me lessons that helped my adjustment. I felt a duty and responsibility to pass those lessons along. When I got out, I wanted to continue following those lessons, but I also wanted to impact the lives of millions of others. In my view, mass incarceration represented one of the great social injustices of our time. Improving outcomes for people who went through the system felt like a goal worth pursuing.

But I also would need to earn a living. To build a career around my journey, I needed to create products that would communicate a message. Specifically, I wanted to document the journey. Others would like resources to sustain energy and discipline over a long period. They would also need guidance on how to stay focused in the short term.

I began creating resources that I could use to teach others.

Some readers may be familiar with self-help literature. From my perspective, self-help literature reveals a similar recipe. People succeed when they follow a pattern that others have used to achieve high levels of success.

  • Socrates began revealing that pattern more than 2,500 years ago.
  • The Bible told those same stories more than 2,000 years ago.

Since the invention of the printing press, we’ve used printed words to convey ideas. Those ideas reveal patterns that anyone can follow.

The journey of life always includes struggle. A person will struggle through life, whether in prison or in society. We can always find strategies to make it through if we read about others. Authors have written about that pathway in self-help literature since the beginning of the printed word.

We read that message through the writings of Socrates, Mahatma Gandhi, Viktor Frankl, Nelson Mandela, and Aleksander Solzhenitsyn. We read the same message from people who studied struggle and figured out ways to overcome it. Work that makes this truism self-evident includes the writing of Stephen Covey, Joel Osteen, and Anthony Robbins. We see the same message in the careers and contributions of Jack Welch, Bill Gates, and Steve Jobs.

What is a coherent message?

  • Leaders begin by clearly defining success.
  • They contemplate the pain or challenge they’re experiencing at a given time.
  • They consider steps to a better outcome.
  • They create a plan that will lead them to success.
  • They understand how to set priorities.
  • Then they execute the plan.

Individuals who aspire to succeed always follow that pattern. Those who reach their highest potential follow the pattern in sports, business, politics, marriage, and in any area of life where they want to excel. They always know where they are and where they’re going. They create plans and strategies, and make decisions in accordance with those plans and strategies.

To build a career around my journey, I needed to craft products and services that would communicate that message. With that end in mind, I began writing specific books.

I wrote Earning Freedom: Conquering a 45-Year Prison Term to show people how to build strength while crossing through years or decades of struggle. Earning Freedom provides many details I left out in this synopsis. It begins with the day of my arrest, on August 11, 1987, until the day that I transitioned to a halfway house, on August 13, 2012.

I wrote Prison! My 8,344th Day because I wanted readers to see what it meant to make disciplined decisions daily, regardless of external factors. The book provides a glimpse of a typical day during my 23rd year of confinement. I begin the book by writing about my eyes opening in the morning. The book concludes when I lie down on my rack to sleep. It covers a single day, describing what it means to make disciplined, deliberate decisions while living amidst persistent challenges.

Then I wrote two separate books to describe the deliberate strategy I teach. I wrote Triumph! The Straight-A Guide for adults in the criminal justice system, and I wrote Success! The Straight-A Guide for At-Risk Youth for juveniles. Each book conveys the same message, but I wrote them for specific audiences.

In writing those books, I intended to build products I could use to advance my career upon release.

Since the day Carole married me in a federal prison’s visiting room, authorities transferred me to the following institutions:

  • Florence, Colorado
  • Lompoc, California
  • Taft, California, and
  • Atwater, California

With each transfer, Carole packed up and moved so we could spend as much time visiting as possible. Together, we made plans for the life we would build when I got out. She became a certified nurse’s aide. Then, after working through the prerequisites of nursing school, she earned credentials to work as a licensed vocational nurse, then in 2010, she became a registered nurse.

We chose nursing for her career because nursing would allow her to earn a livable wage regardless of where authorities sent me. Further, by acquiring a license to practice as a registered nurse, we anticipated that Carole would earn a sufficient income to support our family after my release. Her earnings would allow me to work toward building my career—a career that I anticipated would take several years to develop.

While I worked to create a regular income stream or multiple income streams, Carole’s earnings as a nurse would bring stability to our family.

Readers with time to serve in prison should anticipate income streams upon release.

  • Where will your income originate?
  • How much will you earn?
  • How will those earnings advance your stability?

By using the Socratic questioning approach, Carole and I could make plans to advance our success prospects.

Since I served longer than a quarter century, I didn’t have roots anywhere. As we approached the end of my term, we had to figure out where we wanted to live. We chose California because I considered the state a big market that offered the best opportunities for me, given the support network I’d built. Besides the possibilities, I liked the weather.

Toward the end of my sentence, while confined in a camp near Bakersfield, California, I met Justin Paperny. Justin had built a career as a stockbroker before getting into trouble with the law. He served a relatively brief sentence for violating securities laws.

We became friends. Justin’s conviction meant he needed to create a new career upon release. In 2008, the nation’s economy deteriorated, sinking into the most significant recession of our time.

I used Socratic questioning to help Justin see the challenges that awaited him.

  • “How do you plan on earning a living when you get out?”
  • “How will the market respond to your conviction?”
  • “Why would a manager hire you when so many people without felony convictions are looking for employment?”
  • “In what ways could you turn your experience of going through the criminal justice system into a strength?”

Those questions stumped Justin. He didn’t know how to answer because he limited his thoughts to why prosecutors and a judge put him in prison.

With questions, he could see the societal problems. We could work together to build solutions.

Millions of formerly incarcerated individuals would face the same challenges that would complicate Justin’s life once he got out. Prison isn’t the only problem. We saw a massive problem with all that transpired after prison. People would need to transition into the job market.

I suggested that Justin join efforts I’d been making to create programs and services that improve outcomes for the formerly incarcerated. We launched a plan that would leverage our strengths. Although I would have to serve three more years in prison, I could use my time to write programs, lessons, books, and courses. Since Justin would be free, he could leverage the resources I created, using them to achieve our objective of improving outcomes for justice-impacted people at every stage of the journey.

When Justin completed his prison term, he established a nonprofit. With an authorized nonprofit, I could begin writing proposals for grants to fund our work. Those efforts led to us receiving funding from philanthropic foundations. They provided resources to grow. Through our work, we could build solutions to improve outcomes for people in our nation’s criminal justice system.

Had I not learned to ask the right questions early during my prison journey, I would not have been able to plan. Without a plan, I wouldn’t have a personal-development guide. The project helped me to set priorities. First, I worked to educate myself and build credentials. If I hadn’t earned credentials, I wouldn’t have been able to persuade publishers to bring my books to market. If I hadn’t brought books to market, I wouldn’t have persuaded foundations to provide financial resources.

I’d need to continue that same strategy upon release.

Setting clear goals characterized my entire journey in prison, and the strategy still guides me today. When I reached the end of my sentence, I knew what I would need to ease my transition into society. At a minimum, I wanted:

  • Sufficient savings to sustain me for the first year in society.
  • Income opportunities waiting.
  • A clear plan to guide me through the first year.

I’m hopeful that readers in custody will see the relationship between decisions and success. I believe those who make conscientious, values-based, goal-oriented choices have a greater chance of success than those who simply allow the calendar pages to turn.

The skills I developed during the first decade of imprisonment led to opportunities in subsequent decades. They helped me create opportunities to add value in society. I could also add value for other people in prison, helping them write their books.

Although prison rules prevented me from “running a business,” by understanding how the system operated, I could find ways to balance. Every decision contributed to a systematic plan to ease my transition upon release. Executing that strategy every day allowed me to return to society strong.

Carole and I had more than $85,000 in the bank on the day of my release. More importantly, we had a plan to guide our future.

I did not originate the strategy to succeed upon release. Lessons from leaders empowered me through the journey. Those same lessons can empower others. In writing books, I shared what I learned from the world’s leaders. Even in the context of a prison experience, those lessons advance prospects for success. Through those books, I documented the result of making values-based, goal-oriented decisions.

The remainder of this book will describe how other people in prison can do the same.

Regardless of where you are today, what decisions you’ve made in the past, and what conditions you’re living in, you have the power to begin sowing seeds for a brighter future.

Remember that every decision comes with opportunity costs. To the extent that you adhere to a disciplined, deliberate, strategic path, you can build a life of significance, relevance, and meaning.

Self-Directed Questions:

  • Who are your avatars, and how do they relate to the success you want to build?
  • What would they expect of you?
  • In what ways are the decisions you’re making today leading you closer to earning support tomorrow?

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