Preparing and Supervised Release 

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Sequence 50

39-Preparing and Supervised Release

Early in the journey, I identified the values and goals that would characterize my adjustment through prison. I wanted freedom as soon as possible. I wanted to build a career and stability upon release. I would need support from the probation officers supervising my release to succeed.

Many years before I finished my term, I began preparing to build a record that would result in the best experience on Supervised Release. In prison, I stayed out of trouble. A clean disciplinary record would have a positive influence on my probation officer. To validate my preparations for success, I earned two university degrees, many certificates, published books, and built a strong support network. In its totality, I hoped my prison record would make a favorable impression on the probation officer assigned to my case.

By 2011, I had more than 23 years of prison behind me, and I had advanced to within a few years of my release date. I set a goal of writing a monthly letter to the federal probation office, hoping to influence the probation officer that would supervise me. I didn’t know the probation officer, but if I wrote the letter, I hoped to reach someone of influence.

In the initial letter, I introduced myself. I told the probation officer how hard I worked to prepare for a law-abiding, contributing life from the start of my sentence. I also explained the career that I wanted to build. The subsequent 24 monthly letters provided an update. As an example, the followed a pattern:

Dear Probation Officer:

If you’ve read my previous letters, you know about my commitment to prepare for success upon release. While I work through these final months of my lengthy sentence, I consider it important to connect with the leaders that will supervise my release. For that reason, I’m continuing to send these updates.

If you haven’t done so already, I encourage you to review my release plan. I published my release plan on my website, at It shows the way that I began to architect a plan for release at the start of my journey. It led to my following a principled path, including:

  • Earn academic credentials,
  • Contribute to society,
  • Build a positive support network of mentors.

Those strategies influenced a release plan that I’m still building upon today. It influenced the books I read, the courses I completed, the friends I chose. Because of that plan, I opened a broad support network that will support me upon release. It even led to my getting married inside a prison’s visiting room.

Since writing you last, I’ve opened new opportunities with universities. Relationships with people in academia are part of my strategy to work toward prison and sentence reform upon release.

Although I know that rules prohibit people who leave prison to interact with other justice-impacted people, I am hoping to earn your support. I will seek permission to build a career around my journey. That career will require me to travel and interact with others who have criminal backgrounds.

My release plan clearly shows how hard I’ve worked to prove worthy of your trust. I a hopeful you’ll support those efforts. 

I look forward to discussing my release plan with you further when I’m released.


Michael Santos

Number 16377-004

Probation officers didn’t write back. I didn’t have any way of knowing whether anyone read those letters I sent. But in August of 2013, I concluded my term with the BOP. When I went to meet with my probation officer, she was aware of how hard I worked. Those efforts I made to influence her yielded a great return on investment of time and energy. The probation officer gave me a much higher level of liberty. She allowed me to travel, and she approved my request for permission to build a company that would necessitate my interaction with other people that had criminal charges or convictions.

That is an example of how the Straight-A Guide got me through prison and led to my success upon release. As I became aware of opportunities, others became aware of my efforts to succeed.

From a prison cell, I could choose what I wanted to learn. Like anyone else, I could learn from people I would never meet. Leaders offered valuable lessons. 

I chose lessons that would put me on a path to success. I wanted to learn the patterns of people with a record of succeeding in their chosen fields. They knew what they wanted and made deliberate choices. Aware of opportunities, they marketed themselves in ways to make investors aware of their work. The more aware investors became of leaders, the more resources investors provided. 


What would you like your future probation officer to know about you?

In what ways could you develop a release plan that would help you influence your probation officer?

How will your accountability logs reflect your commitment to your release plan?

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