Super SMART Goals 

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Lesson 8: Super SMART Goals

What you get By achieving your goals is not as important as what you become by pursuing your goals.

—Henry David Thoreau

Take 10 Minutes

8-1: What did you do yesterday? 

8-2: How did your decisions move you closer to the person you intend to become?

Asking such questions strengthened me while serving time in prisons of different security levels. It helped me to obliterate misdirected ideas that I would have to wait for prison administrators to offer programs. Although I could take advantage of every program available, circumstances often changed in prison. Sometimes administrators locked the institution down, or funding cuts or lockdowns could suspend classes. 

Even in unusual times, a person could engineer a personal plan to prepare for success upon release.

All people who question what they’re doing today to prepare for tomorrow can make better decisions. Those questions can lead to incremental steps that restore confidence and lead to better outcomes.

In August of 2013, when I transitioned from prison to Supervised Release, I had a higher level of liberty, and more opportunities. Had it not been for the lessons that masterminds taught, the Probation Officer overseeing me would have restricted my movements. Yet by showing a release plan that showed a pattern of defining success and setting clear goals at each stage of the journey, the Probation Officer allowed me to:

  • Work independently, as an entrepreneur,
  • Interact with other people who were going through various stages of the criminal justice system,
  • Travel domestically at my discretion for the advancement of my career, and
  • Enjoy a higher level of liberty than others would have anticipated.

Those liberties after prison opened because of the preparations I made while going through the journey. To prepare for higher levels of liberty upon release, consider two concepts: 

  • Our values define how we live, what we are, and what we consider success.
  • Our incremental goals advance us along our journey.

I’ll reveal how those concepts influenced me through the 26 years that I served. Further, I’ll show how adjustment strategies through decades in prison opened opportunities along the way. 

I pledge that throughout this course, I’ll never ask anyone to do anything I didn’t do while in prison and that I’m not still doing today. In that manner, I hope to earn the trust of people who choose to continue participating in this program.

The previous lesson emphasized the importance of identifying the values by which we live. According to the masterminds who taught me how to prepare for success, we need to define our values. Once we understand what we’re striving to achieve, we can set clear goals to close the gap between where we are today and the success we want to reach. 

Working toward goals can help us advance.

As I wrote in earlier lessons of this course, Frederick Douglass, inspired me with how he used his life story to advance a cause. When he escaped from slavery, he invested his time and energy to become a force to emancipate all people in slavery. To succeed, he understood that he would have to communicate better. He set a goal of literacy and trained himself to read and write. Then, through three biographies that he published. Mr. Douglass used his life story to build strong coalitions, convincing voters to abolish slavery laws.

When I began serving a lengthy prison term, I visualized how I wanted to return to society. Even from the confines of a solitary cell, I could see myself wearing a suit and tie and speaking in front of an audience. Like Mr. Douglas, I hoped to persuade people that we could improve outcomes of America’s prison system if we changed the way we measured justice. Instead of waiting for calendar pages to turn, we should create incentives. Staff members could use those incentives to reward people for working to develop skills that would prepare them for success upon release.

To succeed, I would have to emulate Mr. Douglass. First, I would need to become more literate. If I could become a published author, others might take me more seriously. Rather than dismissing me as a convicted felon, the people would accept me as a contributing member of society. They might assess the ideas differently, judging me for the man I became—and not for the bad decisions that led to my imprisonment. 

Since I could visualize success, which I’ll describe in future modules, I could lay out a plan. As I wrote in the previous module, I laid out three value categories. To recap, I committed to spending every day working:

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

Those value categories felt consistent with how I defined success. I anticipated that my avatars would recognize and respect those value categories. I wanted to walk into any group of law-abiding citizens and fit in. Whether I stood in a bank, a prospective employer’s office, or a business, I wanted people to accept me. If I didn’t reveal my past, no one would know I served a day in prison. If I succeeded, I would find support and opportunity. If I built credibility in those incremental ways, I might become more effective in advocating for prison and sentence reforms.

The strategy of earning academic credentials, contributing to society, and building a support network helped me frame decisions. Avatars would believe in my future if I lived by those values. 

Defining values would be the start toward building a better life—and I defined a better life as one that would free me from problems with the criminal justice system. Once I got past those problems, I would be more effective as an agent for change that would open opportunities to liberate others when I got out.

By living this values-based, goal-oriented strategy, I hoped to influence people that had discretion over my life. Those people may not have the power to release me from prison, but they could play a role in opening opportunities for me to make further progress. Before I could persuade others to change laws, I would need to persuade people that worked in prisons. They could include the incremental progress along the way. For example:

  • A case manager may recommend me for lower security. 
  • A lieutenant may refrain from citing me with an infraction. 
  • A warden may consider a special request. 

Those leaders had discretion. Their decisions could ease my adjustment or exacerbate my problems. If I made good decisions, I could influence administrators and teachers in prison. They might view me more positively if I developed a values-based adjustment strategy while I served my sentence.

Likewise, by making values-based decisions, I believed that I could influence my future. A probation officer may consider my adjustment. An employer would want to know why I’m worthy of a job. People that had the discretion to approve loan requests would like an explanation of my criminal background. I considered all those people as my avatars. My values would influence their perceptions and my prospects for success.

Before I could work to change laws, or advocate for incentives in prison, I first had to change my life. A jury had convicted me of crimes that led to a 45-year sentence. I had the onus of achieving a series of incremental goals. Otherwise, people would not take me seriously. 

If I could make a favorable impression on my avatars, I could open better opportunities. Preparing for success required me to start my adjustment strategy deliberately, relying upon values to guide my decisions. The opinions of others wouldn’t carry weight if those opinions did not align with how I defined success. 

Many people in prison expressed different values. They focused on their time inside.

Take Ten:

8-3: How are values influencing your life today? 

8-4: How will people you meet in the future relate to your values?

8-5: Describe the people who share the values that you use to define success.

As mentioned earlier, people in prison often give unsolicited advice. They have clear ideas on how to serve time. Some people mistakenly believe that they can’t influence life beyond prison walls. They make decisions to ease their life in jail or prison. They think it’s a waste of time to think about the outside and that such thoughts complicate time inside. While serving a sentence, they say it’s best to forget about the world outside prison.

I didn’t think like a leader before I went to prison. I didn’t give much thought to my future. Since I wasn’t thinking about my future, my decisions didn’t matter. That type of thinking led me to problems. I didn’t know how my decisions and actions influenced the lives of others. Instead of thinking about my role as a citizen (as I later learned from masterminds), I focused only on myself. That thinking led to bad decisions and actions leading to my prison term. 

Making a Change:

I wanted a different life. During the many months of my pretrial detention, I saw and heard a lot. Hundreds of prisoners told me their stories. Many described serving time previously and spoke about the problems they faced after release.

Ironically, men spoke as if serving multiple terms gave them credibility. They were prison leaders dispensing advice. Indeed, they cultivated solid images as stand-up convicts. People in the jail “respected” them. Those cellblock leaders:

  • Decided which television shows other people could watch,
  • Influenced who could sit in which seats in common areas, and
  • Perceived themselves as being stand-up convicts. 

Such strategies and tactics may or may not lead to influence in prison communities. Yet in the broader community, people expect different adjustment patterns. For example, when going to a restaurant, no one knows or cares about people seated at a nearby table. When getting fuel, people typically don’t concern themselves with the decisions of other customers. 

  • How does a stand-up convict differ from the path to preparing for success upon release?
  • How would the avatars I chose respond to someone that built a reputation as a stand-up convict? 

Those types of critical-thinking questions helped to guide the adjustment strategy I engineered.

When I understood that my conviction carried a mandatory-minimum term of 10 years, I knew that I would have to overcome many obstacles. Although ten years would be the minimum sentence, I could anticipate that my judge would inflict a much longer sentence. The statute gave the judge discretion to impose a life term. 

Regardless of sentence length, my adjustment inside would influence my future. Even if the judge sentenced me to serve a life term, I could still work toward influencing a better outcome. I aspired to leave prison with my dignity intact at the earliest time.

My definition of success has always remained at the forefront of my mind. For that reason, these modules will repeat the three value categories that helped to frame every decision I made. I thought of how my choices would relate to:

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

The pursuit of those three value categories would define my adjustment strategy. 

Anyone serving a lengthy term in prison (and I understand that a single day in prison might feel like a long term) could benefit from investing the time to describe their value categories. That exercise in personal development is essential for a person determined to grow. We all need clear goals.

Setting Goals:

We show our commitment to our value categories by setting clear goals. In my case, I understood that achieving goals would influence the perceptions of my avatars. Both the values and goals worked together. A values-based, goal-oriented adjustment strategy would prepare me for success, just as a values-based, goal-oriented adjustment could prepare anyone for success.

On the flip side, pursuing a reputation as a stand-up convict would be another option. That strategy would bring different consequences. The supplemental videos we offer with our courses profile people who talk about their prison journey. The people who spoke with me discussed how their early adjustment strategies in confinement (or lack of adjustment strategies) led to problems. Without direction, individuals that did not set goals found new problems with administrators, or they had problems with other people serving time.

Let’s think about how we want to emerge from challenging situations. We can set clear goals that may open new and better opportunities. Good goal-setting strategies may also lessen our vulnerability to further problems.

Defining a Stand-up Convict:

During the awkward months in pretrial detention, I heard many people offering unsolicited advice on how to serve time. They spoke about the importance of building a prison reputation. Rather than creating a “prison reputation,” however, the decisions we make every day build our life reputation—not only while we’re in prison, but always. Our choices put us on track for success or lead us into cycles of failure. People that identified as “shot callers” in jail sometimes revealed that they had complicated lives outside of confinement. In other words:

  • They didn’t have good credit scores.
  • They didn’t own a home.
  • Their most prized possession was a vehicle of some sort.
  • They didn’t have financial resources.
  • They didn’t have stable careers.
  • They couldn’t buy items in the commissary.
  • They didn’t have steady relationships.
  • They didn’t have close or supportive families.
  • They described problems with substance abuse or other addictions.
  • They complained of ongoing problems while on supervised release.
  • Their family members had issues with the criminal justice system.

If that story applied to one person in prison, it would be easy to dismiss. Yet by the time I served a few months in custody, I heard similar stories from everyone who identified themselves as being leaders in prison. I saw a pattern. The way that a person adjusted in prison would influence the prospects for success after release. 

People who valued a prison reputation minimized chances to live the way they envisioned after release.

As you work through this self-directed course, think about the life you want to lead upon release.

After a jury convicted me, I understood that prisons would confine me for at least a decade. I couldn’t change that fact. Yet, I had the power to choose how I would adjust, and the adjustment strategies would influence my prospects for success once I got out. The value categories of focusing on education, contributing to society, and building a support network would influence the goals I set along the way. 

  • What clear goals would show a commitment to those values? 
  • Would they put me in a better position to succeed? 

I wanted to succeed in prison and beyond.

Participants may want to engineer a new adjustment strategy to guide decisions going forward. 

Take 20 Minutes

8-6: How can you use these lessons to start changing your life today?

8-7: What relationship do you see between your circle of friends and your prospects for success—as you defined success with your values?


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.

Take 10 Minutes:

8-8: What SMART goals can you set to convert your adversaries into your advocates?

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