Blog Article 

 2—Success after Prison 

Picture of Michael Santos

Michael Santos

Need Answers to Your Questions?

If we’re losing hope from the challenges we face, Socratic questioning can help us find our way to success after prison. What would our avatars expect?

The Beginnings: Socrates and Success

I’m typing this manuscript on a fabulous iMac computer. When I served my sentence, I had to write manuscripts by hand. Since getting out, I’ve become addicted to technology products by Apple, Microsoft, Adobe, and Google. I use them every day. These tools allow me to write more efficiently and become more productive.

Institutions control people’s time while they serve sentences, but people must work productively once they get out. Employers resist hiring people who do not know how to use technology.

The internet didn’t exist when I started serving my sentence. Until I got out, I never sent an email, used a smartphone, or made a video. My wife got me a MacBook Pro within days of getting out, and I began training. Although I didn’t get to use computers while I served my sentence, the books I read and the courses I took inside positioned me to learn quickly once I got out.

I started typing the first version of this manuscript on Saturday morning, December 4, 2015. I aimed to complete the manuscript and publish the book before the new year. To reach that goal, I would have to apply myself. I didn’t want to squander an opportunity that opened to connect with people serving time.

Warden Andre Matevousian invited me to make a presentation at the United States Penitentiary in Atwater on January 8, 2016. Before I got there, I wanted to write a book to help people inside see how their decisions could lead to success upon release. I knew that staff members and other leaders tried to convey that message. Somehow, I thought the men would find more meaning in the message if they heard it from a person who went through prison and returned to society.

The Warden asked me to talk with the men about the importance of setting clear goals. Since I never asked anyone to do anything I didn’t do, I set a goal. I would write the manuscript, publish the book, and show the tools I created to hold myself accountable. People in prison should see how small and incremental steps lead to bigger goals that can open new opportunities.

While incarcerated, I learned the power of seeing far into the future. I would need to use time wisely to build the future I wanted. Every decision came with an opportunity cost. Decisions would either move me closer to success or complicate my life in ways that could lead to more problems.

The roots of my invitation to speak at USP Atwater began many years earlier. In many ways, I would argue that I started sowing the seeds for that invitation back in 1987 while I was locked inside the Pierce County Jail, waiting for sentencing. I read a book about Socrates, and he inspired my adjustment through prison. Instead of dwelling on the problems I created for myself, Socrates taught me to start thinking about the future I wanted to build. That book influenced the decisions I made in prison.

My adjustment influenced my transfer to the federal prison in Lompoc in 2004, during my 17th year of imprisonment. When I got there, Andre Matevousian served as the Captain at Lompoc, meaning he led the custody and security staff.

While I was in Lompoc, The Los Angeles Times published a review for my book Inside: Life Behind Bars in America. When a correctional officer saw the review, he cited me with a disciplinary infraction for “running a business.” He led me into the Special Housing Unit, and from there, I began using the administrative remedy process to contest the appropriateness of the disciplinary infraction. Through that experience, I got to know Captain Matevousian. After the region agreed to expunge the rule violation, administrators ordered my transfer from Lompoc to a camp in Taft, California.  

I didn’t see Warden Matevousian again until 2015, following my luncheon keynote speech at the judicial conference in Sacramento. Warden Matevousian approached and congratulated me for the career I had built since getting out. He extended an open invitation to visit Atwater—the prison that released me in 2013—so I could meet his team and speak to the people inside.

I welcomed the opportunity.

Since concluding my journey as federal prisoner number 16377-004, I’ve worked to build a career around all that I learned. To provide some context, I owe readers at least an abbreviated background.

Those who’ve read my earlier books, particularly Earning Freedom: Conquering a 45-Year Prison Term, won’t learn anything new in this chapter. I won’t take the time to provide the same level of detail I wrote in that comprehensive book. For those who have not read Earning Freedom but want a wider glimpse of my prison journey, visit to get a digital copy of Earning Freedom. Libraries may offer copies of the paperback or audio version.

After this initial chapter, the remaining chapters of Success after Prison will show how decisions in prison relate to opportunities that opened since my release. We’ll start with the backstory.


In 1982, I graduated from Shorecrest High School in Seattle as a mediocre student. Immediately following graduation, I started working in a contracting company my father began during my childhood.

My father escaped from Cuba and worked hard with my mother to build his company. He hoped to pass the business along to me after I matured, but I disappointed my mom and dad during my reckless adolescence.

When I was 20, in 1984, I saw the movie Scarface with Al Pacino. Pacino played the character Tony Montana, a cool Cuban immigrant who built a fortune trafficking cocaine. Rather than following in my father’s footsteps, I made the bad decision to follow guidance from Tony Montana.

Tony said, “In this country, first you get the money, then you get the power, then you get the woman.”

From my immature perspective, I admired Tony’s philosophy. As the film’s closing scenes depicted, his outlook on life didn’t work out so well.

Nevertheless, after watching the film, I coordinated a scheme to earn quick money by distributing cocaine. Foolishly, I believed that I could shield myself from prosecution. By limiting my role to negotiating transactions and hiring other people to transport the cocaine or storing the cocaine, I convinced myself that I could avoid the criminal justice system.

On August 11, 1987, I learned how badly I had misinterpreted the criminal justice system. In the late afternoon, I saw three DEA agents pointing guns at my head. They ordered me to put my hands up, searched me, and as they locked my wrists in steel cuffs behind my back, they let me know of their warrant for my arrest.

My odyssey through the criminal justice began. When I refer to the journey as an “odyssey,” I allude to Homer’s classic Greek mythology. Homer wrote about Odysseus, who had gone on a long journey to fight a war. He had to endure many trials and tribulations before returning home.

Over the decades that followed my arrest, I’d go through the following:

  • Federal holding centers,
  • Court proceedings,
  • Jails,
  • Federal transit centers,
  • Many Prisons,
  • Halfway house,
  • Supervised Release,
  • Parole, and
  • Special parole.

The following pages tell the story of how decisions I made inside influenced my life outside. I hope this message inspires other justice-impacted people to prepare for their odyssey and successful outcome.

Transformation after Trial

Wanting nothing more than to get out of jail, I welcomed the optimism I heard from my attorney after the arrest. When he told me that a significant difference existed between an indictment and a conviction, I put my future in his hands.

Then I proceeded to make every wrong decision a defendant could make:

  • I refused to accept responsibility.
  • I didn’t contemplate expressing remorse.
  • While in custody, I stayed involved with the criminal enterprise I had begun.
  • I took the witness stand to testify during my trial and lied to the jury.

Members of the jury saw through my perjury and convicted me of every count.

A New Philosophy:

After the jury convicted me, the US Marshals returned me to the Pierce County Jail. While in my cell, I came to terms with the bad decisions I had made for the first time. I began to pray for guidance. Those prayers led me to a philosophy book, and I came across the story of Socrates.

At that time, I didn’t know anything about philosophy or Socrates. While reading the early chapters, I learned that he served ancient Athens as a teacher. Laws of that era criminalized the ruling class from teaching people of lower classes.

Socrates broke that law. He believed that every human being had a right to learn. Authorities arrested him and put him on trial for violating the law. Following his conviction, the judges sentenced him to death. They ordered jailers to confine him until his execution date.

While waiting for authorities to carry out his death, Crito, a friend of Socrates, visited him in jail. Crito presented Socrates with an opportunity to escape.

Instead of taking the easy way out by escaping his punishment, Socrates chose to stay. He would accept death before dishonor.

From Socrates, I learned a great deal. The book described his mindset, and I learned from the brilliant questions he asked, known as “Socratic questioning.”

After reading several stories about his life, I stretched out on the concrete slab in one of Pierce County’s jail cells. As I stared at the ceiling, I contemplated the many bad decisions of my youth, trying to connect their relationship to my predicament:

  • I chose friends poorly,
  • I lived a fast lifestyle, and
  • I lacked discipline.

Those bad decisions led to my selling cocaine, and that crime led me to face a potential life sentence.

Even though my conviction carried the possibility of a life without parole, I believed I would return to society at some point. I began questioning whether I could do anything while serving my sentence to prepare for a better life when my prison term ended.

From Socrates, I learned the secret to success. Instead of complaining about the troubles my past decisions created, I needed to question the relationship I wanted with the broader society.

Later, I learned from many other masterminds. They taught me the timeless value of asking the right questions. For example, a well-known sales coach and motivational speaker, Zig Zigler, is famous for having said:

“If I help other people get what they want, I can get everything that I want.”

Zig Zigler

Reading about Socrates taught me to ask questions that would help me understand the people I wanted in my life. I hated confinement and didn’t want to be a prisoner forever. Although I couldn’t undo my past bad decisions, I started thinking about the people I wanted to interact with in the future.

Ironically, although I faced a life sentence, I didn’t want to think of myself as a criminal. In the future, I wanted others to judge me for how I responded to my problems—not for the bad decisions that resulted in my imprisonment.

Socratic Questioning and Avatars:

  • Who were the people I would want to interact with in the future?
  • What did they do for a living?
  • What influence would they have in my life?

Those kinds of questions led me to “humanize” my avatars.

What’s an avatar?

From my perspective, avatars were the type of people I wanted to meet in the future. They would influence aspects of my life. Although they didn’t exist as flesh-and-blood people, in my mind, the avatars were lifelike—even though I didn’t know who they would be.

  • I thought about my future probation officer because that person would influence my life whenever my prison term ended.
  • I thought about my prospective employer.
  • I thought about future lenders.
  • I thought about the woman I would marry and the friends I would choose.
  • Who were those people?
  • What characterized their lives?
  • What level of education would they have?
  • What could I do to earn their respect?

The more I contemplated my avatars, the more insight I had as I considered how I would adjust through my prison journey. I began with questions about whether there would be anything I could do to influence how those avatars would perceive me in the future.

The initial answer to my question was a resounding yes.

If I acted appropriately, I believed I could influence my avatars’ perceptions.

As Socrates taught, one question always leads to another:

  • How could I influence the perceptions of those avatars?
  • What would they expect from me?

Those questions led to a three-part plan:

  • My avatars would expect me to educate myself.
  • My avatars would expect me to contribute to society.
  • My avatars would expect me to build a support network.

If I kept the expectations of my avatars at the forefront of my mind, and if I turned to those thoughts with every decision, I believed that I would influence perceptions. Instead of judging me for my criminal conviction, being a prisoner, or an ex-convict, my avatars would respect me. They would perceive me as a man of discipline and integrity, someone who worked to earn his freedom.

Self-Directed Questions:

  • If you could influence someone, who would you want to influence?
  • What do you know about that person?
  • In what ways would influencing that person change your life?
  • What steps could you take today to influence that person?

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