January 6, 2026: Tuesday

Setting Goals

In the first lesson, I wrote about the importance of defining success. That step always comes first. Once you define success, the next question becomes obvious:

How will you move toward it?

Goals provide the answer. If defining success gives direction, setting goals provides structure. Goals turn intention into action. They give shape to effort, especially during times of crisis or uncertainty.

While in prison, I found this tactic of setting goals essential. Confinement removes many choices, but it does not remove the ability to plan. When you set goals, you take another step toward living as if you are the CEO of your life. Instead of reacting to circumstances, you begin managing them.

Learning to Set Goals in Prison

I was still incarcerated when I first learned about the concept of SMART goals. The idea made an immediate impression on me because it offered structure at a time when my future felt uncertain.

From reading, I learned that George T. Doran introduced this concept of the SMART framework in a 1981 article titled There’s a S.M.A.R.T. Way to Write Management’s Goals and Objectives.

The SMART acronym stands for:

• Specific – clearly defined
• Measurable – trackable
• Achievable – realistic given circumstances
• Relevant – aligned with your definition of success
• Time-bound – connected to a deadline

These concepts made a lot of sense to me, given that I was at the start of a lengthy prison term, and already trying to follow the principles of being “The CEO Of my Life.” I understood that there was a problem all people in prison faced. It wasn’t only the time we were serving, it was also the likely outcome. From my studies, I anticipated that most people would face one of five likely outcomes:

1. People would leave prison to face unemployment.
2. They would be under employed, working in jobs that didn’t lead to stability.
3. They would struggle through the crisis of being homeless.
4. They would have more problems with the law.
5. They would be successful.

To be successful, people would have to overcome the feeling of being disoriented in prison. Instead of focusing on a prison reputation, to succeed, people would need to think beyond the struggles that come with long sentences, where outcomes are delayed.

When I read about SMART goals, I found a strategy to counter those forces. They shrink overwhelming timelines into manageable steps. They allow a person to measure progress even when freedom feels far away.

For me, SMART goals became a way to regain control.

From Philosophy to Action

Earlier in this course, I wrote about how reading about Socrates influenced my thinking while I was in solitary confinement. His method of asking disciplined questions forced me to confront what truly mattered.

Instead of asking when I would get out, I asked:

• Who do I want to become?
• How can I prepare now for the people I will meet later?
• What actions are within my control?

Those questions led me to a simple, three-part strategy:

1. I would educate myself.
2. I would contribute to society in measurable ways.
3. I would build a strong support network.

By defining success, I could decide what mattered to me, what I valued most highly. SMART goals helped me decide how to act.

Structuring Goals During Confinement

Although I could not control my release date, I could control how I worked toward my plan. SMART goals gave structure to each part of my strategy.

• Education: I set a goal to earn at least one university degree within ten years.
• Contribution: I set a goal to become a published author within ten years.
• Support Network: I set a goal to identify and build relationships with ten mentors within ten years.

Those goals were specific. They were measurable. They were realistic given my circumstances. Most importantly, they gave me direction during years when uncertainty could have led to stagnation.

Goals Change by Stage

Just as success changes by stage, goals must change as well.

During confinement, it helps to think in three time horizons:

• Short-term goals (30 to 90 days): building routines, completing courses, improving health, journaling consistently.
• Mid-term goals (1 to 3 years): earning credentials, teaching others, building documented contributions.
• Long-term goals (5 to 10 years): career objectives, financial stability, leadership roles, service beyond prison.

A person wouldn’t need to accomplish everything at once. We should strive to pursue excellence, going after goals that fit the stage we’re in now. The life I am leading now is only possible because of the goals I set and worked toward while I was climbing through 26 years as federal prisoner number 16377-004.

I encourage participants to pursue this path. I am convinced they will find that SMART goals allow incremental progress and build intrinsic motivation without burdening anyone with feelings of being overwhelmed.

Carrying the Strategy Forward

After completing my prison term, I continued using the SMART framework. My goals evolved, but the strategy remained the same. One of my early post-prison goals was to earn $1 million within five years. That goal reflected a new stage of life, one that required financial stability and long-term planning.

Over time, I exceeded many of the goals I once believed were out of reach. Yet the process never ended. The more I learned, the more I realized how much further I could grow.

When we’re pursuing goals, we’re building and maintaining momentum. We’re showing our commitment to excellence, to leading a disciplined, values-based life. This pattern helps others see us for more than the bad descriptions in our PSR, or what led us to prison. Instead, they see us as if we’re the CEO of our life, self-directed, self-motivated, always focused on results.

Self-Directed Learning Exercise

Complete the following exercise in writing:

1. Identify one area of focus for your current stage of life
   Examples include education, health, contribution, relationships, or preparation for release.
2. Write one SMART goal you can realistically pursue over the next 90 days.
   Be specific. Be honest about your circumstances.
3. Identify one weekly action that supports that goal.
   This is the behavior you can repeat consistently.

At the end of each week, review your progress:

• Did my actions align with the goal I set?
• If not, what adjustment should I make next week?

This process builds discipline. It reinforces accountability. And it prepares you for the lessons that follow in the Straight-A Guide.