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Sequence 30



Establishing value categories influences our choices. Once I decided to transform my life, I wanted to go on record. I started writing to mark the day when I left criminal decisions behind. I wanted to show my commitment to living as a law-abiding citizen. By writing about that commitment, I drew a line and invited the world to hold me accountable. With that end in mind, I wrote a letter to a journalist in the local newspaper. 

In the letter, I wrote how I regretted selling cocaine. Although I couldn’t change the past, I pledged to the journalist to use my time in prison to make amends. The three-pronged strategy would include a commitment:

  • To earn academic credentials,
  • To contribute to society, and
  • To build a strong, positive support network.

I invited the journalist to visit me in jail with that simple explanation.

That letter represented a step in the right direction. It showed my quest to make things right. Writing the letter made it clear that I wanted to atone. I planted a seed for a new and bright future. The record would show the exact time I made a conscious, deliberate choice to change.

The journalist interviewed me in a small jail conference room. The week before sentencing, the newspaper published the article. That front-page story profiled how I said I would change. I put myself on record, pledging to spend every day working to reconcile with society.

With clear value categories to define success, I could start taking incremental steps to show my commitment to pursuing success. By going on the record, I started moving closer to liberty. As time passed, I would always be able to look back to those writings when I declared that I would never commit another crime.

The Sentencing Hearing:

I expected the prosecutor to oppose my request for mercy. Although I wanted leniency at sentencing, his job required that he pursue a harsh sentence. I anticipated that he would argue that I lacked remorse for the crimes that I had committed. Instead, he would contend that any sorrow I expressed resulted from getting caught.

Exposure to Socrates and philosophy changed how I looked at the world. When I read about Frederick Douglass, I understood that I would need to develop a life story. Instead of hiding from my past, I would need to respond and build a series of incremental progress that would influence a better future. If wanted to work toward changing laws, I would need change myself first. 

Earlier, I lived by a philosophy that aligned with failure. I wanted to make things right. Writing to the journalist and participating in his interview, I believed, showed that I had changed my thinking.

On the day of my sentencing, jailers came to my cell before dawn. When I heard keys approaching, I got ready. They took me to another holding cell so I could change from my jail jumpsuit into my court clothes. Regardless of what term I received, I had my value categories. They would serve as a guide. They would help me build a path home.

Decades have passed since the day of my sentencing. But I will always remember the prosecutor’s words. He told the judge:

“If Michael Santos spends every day of his life working to reconcile with society, and if he lives to be 300 years old, our community will still be at significant net loss because of the crimes he committed.”

After assessing the arguments, the judge presiding over my case sentenced me to 45 years. Strangely, I felt okay with the sentence. Under federal sentencing laws of 1987, I could earn “good time credits.” By avoiding disciplinary problems, I could finish my sentence in 26 years. Still, 26 years felt like a long time, longer than I’d been alive at that point.

We can put that term in perspective. Imagine a young man going into prison today. Project 26 years into the future. Could a young man who began serving that sentence sustain a high level of energy and discipline through the journey?


Still, we should learn and teach lessons that lead to lives of fulfillment and avoid altercations with the criminal justice system.

A values-based, goal-oriented adjustment strategy would bring energy and discipline to my life. Like anyone else, I could set clear goals once I defined success. Those goals would reflect a commitment to the values I set. 

Experts who wrote about goals suggested that we adhere to the acronym “SMART.”

  • S — A goal should be specific.
  • M — A goal should be measurable.
  • A — A goal should be action-oriented.
  • R: — A goal should be realistic.
  • T: — A goal should be time-based

By setting SMART goals, I could work toward success. I defined success with my values. Those goals would help me break up the time. Those incremental goals would keep me going through the decades I expected to serve. Instead of dwelling on time, I focused on moving through the goals, completing one and moving on to the next.

Achieving goals felt like building a ladder. I could climb to liberty, to success. 

Participants may want to set SMART goals that advance prospects for success, as they define it.

I again turned to my avatars to set SMART goals within each value category. Those avatars were like mentors to me—even if I had not met them yet. They included:

  • The probation officer that would influence my life after release,
  • The employer who could open an opportunity for me to earn a living,
  • The creditors that might provide capital I could use to build businesses after I finished my prison term.
  • The professionals who could help me work to change laws and open opportunities for more people to work toward earning higher levels of liberty through merit.

What steps could I take while in prison to influence those avatars? 

That question led me to set the following clearly defined goals:

  • To measure whether I lived by my commitment to educate myself, I needed to earn a university degree within my first ten years.
  • I needed to become a published author within ten years to measure whether I lived by my commitment to contribute to society.
  • To measure whether I lived by my commitment to building a support network, I needed to bring ten people into my support network within ten years.

I would achieve the three SMART goals during my first ten years in prison. I didn’t know how. Yet, the goals became my guide. By completing the goals within ten years, I advanced my prospects for success. Then I could set new goals. The goals brought strength. I started on a path of recreating myself. I began the long process of transforming myself from a reckless youth into the man I aspired to become.

My term in prison began when I was 23, and it didn’t conclude until 2013 when I was 49. Many years have passed since I got out. Experience has given me a different perspective from when I began serving my sentence. 

  • I’ve built businesses that generated millions of dollars in transactions with people in the private sector. 
  • I’ve negotiated business relationships with federal judges, US Attorneys, and directors of prison systems.
  • I’ve influenced judges, prison administrators, and people in academic to become a part of a coalition that would lead to prison and sentence reforms, such as the First Step Act. 

None of those opportunities would have been possible if I hadn’t been receptive to learning lessons from masterminds while serving my sentence.

As I look back, I can see the importance of defining success with values and using goals to guide adjustment strategies. 

From masterminds, I learned that even though I made terrible decisions that put me in prison, I could start making better decisions. Those decisions could help me to grow stronger. The adjustment strategy may not have gotten me out of prison one day early, but it made a colossal difference in helping me to recalibrate and rebuild. I could seize opportunities that would accelerate prospects for success. By using values and goals to define an adjustment strategy, we may emulate masterminds who have conquered past struggles.


What SMART goals can you set to convert your adversaries into your advocates?

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