Lesson 3 

Need Answers to Your Questions?

Sentenced to 45 Years in Prison:

Federal prosecutors brought a charge known as the kingpin statute against me, Title 21 Section 848, also known as the Continuing Criminal Enterprise. When my lawyer described the charge, I didn’t understand. To convict, the prosecutors would need to prove that my crime involved:

  • Three or more overt acts,
  • My supervision of five or more people, and
  • Substantial amounts of money.

Without a doubt, I knew my guilt. Yet rather than accepting responsibility and expressing remorse, I continued to live in denial—believing that I could deceive the jurors and the judge.

Despite the many people that would testify against me, I deluded myself. The jurors heard people testify. They heard from people who said that, at my direction, they rented cars to further the conspiracy, or they purchased airline tickets or rented apartments to transport and store cocaine.

The government may not have had tangible evidence that jurors could hold, but they brought forth many people who told a compelling story under oath. When the judge asked for a verdict, the jurors agreed that prosecutors had proven the case beyond a reasonable doubt. They convicted me on every count.

The statute carried a 10-year mandatory-minimum sentence, with a maximum life sentence. During that awkward transition between the time a jury convicted me and the sentencing date, a correctional officer passed me the philosophy book that told the story of Socrates, which transformed my thoughts.

If we change the way we think, we change our life.

After reading the story of Socrates, I realized I had to change. His story inspired me to stop dwelling on my past. I could use time in prison to become a better person who would be both resilient and realistic.

Socrates prompted me to lay out that three-part plan to guide my adjustment. While waiting for sentencing, I began writing extensively on how I would use time in prison to:

  • Educate myself, as evidenced by a university degree,
  • Contribute to society, as evidenced by publishing, and
  • Build a strong support network, as evidenced by mentors I would bring into my life.

To counter my commitment to change, during the sentencing hearing, the prosecutor gave his perspective:

“If Michael Santos spends every day of his life working to make amends, and if he lives to be 300 years old, our society would still be at a net loss.”Assistant US Attorney Ken Bell

The prosecutor recommended that the judge sentence me to serve a 45-year sentence, and the judge agreed.

The sentencing laws for convictions before November 1, 1987, were different. They incentivized people to use time in prison wisely. I could earn 19 years of good-time credits with my statute and sentence.

For readers who don’t understand the concept of “statutory good time,” it’s an incentive that rewards people for avoiding disciplinary infractions while incarcerated. A person didn’t need to do anything outstanding to earn good time. He simply needed to avoid being convicted of violating disciplinary infractions.

So long as I didn’t lose any good time during my journey through prison, I would satisfy my sentence after 26 years. Since I was 23 when authorities took me into custody, I didn’t quite know how to process the concept of serving 26 years.

Thankfully, by reading Socrates, I had a vision and a strategy. By thinking about my avatars, I could engineer a plan to advance the possibilities of emerging successfully. I would focus on that three-pronged goal:

  • Educating myself,
  • Contributing to society, and
  • Building a support network.

I began serving my sentence in the United States Penitentiary in Atlanta. The prison was thousands of miles away from where I grew up, in Seattle. While locked inside those high walls, I embarked upon the first prong of my plan.

Although I’d been a lousy student in high school, I committed to becoming a good student in prison.


Because I believed that if I could earn a university degree while incarcerated, people in society would respect me. Then I could connect the dots. If more people respected me, I believed that more opportunities would open.

Since I didn’t have any financial resources, I began writing letters to universities. I wrote to hundreds of universities, not knowing whether anyone would read the letters. Still, I knew that if I didn’t write letters, I wouldn’t stand a chance of connecting with my avatars who lived on the other side of the walls. Each letter expressed some version of the same message:

I made terrible decisions as a young man. Because of those decisions, a judge sentenced me to serve a lengthy term in prison. I wrote that I wanted to educate myself while inside and asked for help.

In time, I found universities to work with me. I built my support network inside prison walls from the relationships I opened. The efforts resulted in earning an undergraduate degree in 1992 and a master’s degree in 1995.

After Hofstra University awarded my master’s degree, I began studying toward a Ph.D. at the University of Connecticut. Then a warden determined that my education had gone far enough. He stopped my formal studies by prohibiting the prison’s mailroom from accepting books that the University of Connecticut’s library would send for my coursework.

Fortunately, by then I had eight years of imprisonment behind me. That experience conditioned me to cope well with obstacles. While incarcerated, we must expect obstacles but work to succeed anyway.

When my formal studies came to an end, I shifted focus. As I wrote in Earning Freedom and other books, I went through a phase where the stock market consumed all my time. By studying how investors valued stocks, I learned about business. I became fluent in “technical analysis,” understanding how to assess a stock’s value in accordance with various trading patterns. Reading financial newspapers, magazines, and books, I also learned about “fundamental analysis.” Those lessons taught me the importance of more objective metrics, including growth rates, profit margins, return on equity, and other factors.

Studying the stock market, I knew, would be a poor substitute for real business experience. But my long term in prison required that I look for “unorthodox” ways to prepare myself for success upon release. The more I could learn about business, the more I would arm myself for the challenges I anticipated upon release.

  • What lessons could you learn with the resources you have around you?

In the following pages and chapters, you’ll see how Socrates inspired me to ask those kinds of open-ended questions. The questions would not have a right answer or a wrong answer. Instead, they would prompt us to think and to continue questioning rather than complaining. I learned how to assess the opportunity costs that accompanied every decision.

Those questions helped me to accept that regardless of external factors, such as institutional rules, I could find ways to prepare for the success I wanted to build upon release. Even if the prison didn’t offer classes, I could choose what I would read or what I could study. I could learn as much as possible. We could build confidence by using existing resources to prepare for a prosperous future.

Without a deliberate plan, however, we may not see the resources. Instead, we may succumb to the guidance from other people serving time around us. They may try to influence the decisions we make inside. Their advice could lead us to a different outcome from what we want.

In the following pages, I’ll reveal more about the strategy that worked so well for me. I’ll recommend readers compare that strategy with other adjustment patterns.

As we approached the turn of the century, I crossed into the second half of my sentence. I had 13 years behind me and 13 years of prison ahead of me. I shifted my attention to writing, wanting to advance toward the other two prongs of my adjustment strategy. First, I wrote articles and submitted them for publication. Then I began writing chapters for academic books.

In time, one of my mentors offered to introduce me to his publisher. Professor George Cole, from the University of Connecticut, presided over my Ph.D. program, and he authored the leading textbook on corrections. George suggested I write a book for an academic audience that his publisher could package as a supplemental text for university students in criminal justice courses. His suggestion led to my first book, About Prison.

In retrospect, it’s easy to connect the dots. In earlier chapters, I wrote about how I contemplated my avatars. To recap:

  • While still in the county jail, before a judge sentenced me, I thought about the people I would want to influence in my future.
  • I didn’t know George Cole then, and George Cole didn’t know me. He was a distinguished author, and he led the criminal justice department at the University of Connecticut.
  • While locked in the Pierce County Jail, masterminds like Socrates inspired me. They taught me to ask “Socratic questions” about what steps I could take during my imprisonment to prepare for success. Those questions led to my three-part adjustment strategy:
  • 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.
  • By sticking to that three-pronged strategy, I could open more opportunities.
  • Since I executed that plan, I earned university degrees.
  • Since I earned university degrees, I found it easier to open opportunities to publish articles.
  • Since I published articles, I found mentors like George Cole.
  • George didn’t judge me for the bad decisions that brought me to prison. Instead, he looked upon me as someone who could add value to society. George then introduced me to his publisher. She issued a contract to publish About Prison. Thousands of people became aware of my work when About Prison came out. My support network grew.
  • Since the prison system didn’t allow me to “run a business,” I assigned royalties from About Prison to family members. Those resources opened opportunities I could leverage and create more opportunities.

The cycle of success began when I served time in jail—before a judge sentenced me to prison.

I urge readers to respond to the following question:

  • When will your cycle of success begin?

I’m convinced it will begin as soon as you start living by the same model that leaders taught me:

  • Visualize success by contemplating avatars,
  • Create a plan to persuade avatars to invest time, energy, and resources in your development.
  • Execute your plan with every thought, word, and decision you make while serving your sentence.

After writing my first book, I reached out to another mentor. Dr. Marilyn McShane. Marilyn taught criminal justice courses at several universities. She also advised publishing companies and opened an opportunity to publish my second book, Profiles from Prison, through Greenwood/Praeger, another well-respected academic publishing house.

With two publishing credentials behind me, I aspired to reach a wider audience. Prison populations had been growing, and I thought writing a general nonfiction book about the prison system would be helpful. I pulled books from prison library shelves and researched how to go about publishing a mainstream book.

  • The first step would be to write a book proposal.
  • Then I would need to write sample chapters.
  • Next, I would need to write a cover letter and begin sending self-addressed-stamped envelopes to literary agents.

Research showed that if I could persuade a literary agent to represent me, the literary agent would connect with publishing houses. If editors who worked at the publishing house liked my book, the editor would issue a contract to bring my book to market. It wouldn’t be easy.

Fortunately, living in prison had conditioned me to deal with rejection.

The book proposal required about 30 pages of writing. Sample chapters added another 30 pages. Postage and copy costs would be too high if I were to send the entire package to scores of publishers. I needed to create more economical tactics.

Instead of sending the complete book-proposal package, I leveraged my earlier work.

First, I identified 100 literary agents. Then I wrote a query letter describing my background, educational credentials, publishing credentials, and a few sentences about the type of book I wanted to write. I sent that one-page letter and a self-addressed stamped envelope to the agents. With postage costs and copying, the total cash outlay amounted to less than $2 an envelope—or $200.

  • What value would you place on that $200 investment?

Each person would have to ask such questions. This question helps us appreciate the meaning of the phrase: “The right decision at the wrong time is the wrong decision.”

  • Had I not spent the early years of my sentence working to develop writing and communication skills, I would not have persuaded leaders like George Cole to mentor me.
  • Without mentors like George Cole, publishers would not have brought my earlier books to market.
  • If I didn’t have earlier publishing credentials, a literary agent would not have interest in working with me.

As an orderly in prison, my wages amounted to about $10 per month. The $200 I spent on postage represented more than a year’s worth of income from my job. Yet by sending out those letters, I secured a relationship with a literary agent.

I sent the agent my full proposal. The literary agent secured a publishing contract with St. Martin’s Press within two weeks. The contract came with compensation that brought over 1,000 times the initial investment I made in postage. More importantly, libraries and bookstores across the country began selling the book I wrote for a general, nonfiction audience.

St. Martin’s Press published Inside: Life Behind Bars in America in 2006. The investment of time and energy continues to bear fruit and pay dividends. Twice a year, I receive a royalty check from the publishing house.

Many opportunities opened through the books I wrote. The books persuaded people to believe that I didn’t just “talk” about wanting to live a life of meaning, relevance, and contribution. Those people had tangible proof. They wanted to invest in me, help me, and believe in me.

Any person in prison can begin creating credentials that will advance prospects for success. It’s never too early and never too late to start preparing for a life of meaning, relevance, and dignity.

My adjustment plan had three components that aligned with how I defined success:

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

Self-Directed Questions:

  • How would each of those components work together?
  • What opportunities open for people who strive to contribute to society?
  • How would your efforts to contribute to your community influence leaders to mentor you?

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