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 Disappointment in Prison 

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Michael Santos

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Living in prison will bring disappointments. Every person going through the journey should accept that disappointments will come. We must develop the grit to overcome and persevere, regardless of what decisions others make.

Coping with Disappointment in Prison

When we’re living in challenging times, stories have the potential to give us strength. Those who’ve read Earning Freedom: Conquering a 45-Year Sentence know that the story of Socrates changed my life while I started my term in a solitary cell.

The first time I read about Socrates, I learned about his mindset while he awaited his execution. I felt more receptive to receiving his message because we shared imprisonment in common.

Although few stories are as empowering as the story of Socrates, since I served multiple decades in prison, I hope readers of this email will be receptive to this message I offer. I hope readers will know that I empathize with every person in prison and that I work with one goal: To help people work through the pains of incarceration and prepare for a better life.

Sometimes, while we work toward a better life, we face disappointments. Each recipient of this letter deals with disappointment. Many people do not belong in prison. They’re disappointed that they cannot find a quicker way home.

Today I had some disappointing news. I expected to interview a former leader of BOP, and I hoped to share the information I received with each of you. Unfortunately, the interview got pushed back until Thursday. But I am giving each of you my word that I will continue working on getting answers to your questions. Expect an update by the weekend.

While in prison (and in life), we must anticipate disappointment and work to succeed anyway. I remembered that lesson this morning. When the interview got pushed back, I recalled the many times I received disappointing news in prison.

Those thoughts took me back to the start of my sentence. Since I’d never been in prison before the instant offense, I didn’t know about security levels when authorities sent me to a USP. Whether someone is in high security or minimum security, a person longs for liberty. Like every person reading this letter, I felt the disappointment and pain of being separated from family. Over time, I improved at accepting the many disappointments of prison life.

When I transferred to the medium-security prison after seven years, I appreciated the higher level of liberty. After more years, I went to a low-security prison. That felt even better. When I moved within ten years of my release date, administrators sent me to the camp in Florence.

In Florence, I felt a massive stress level come off. Since I’d gone from high-security to medium-security to low-security, I had a different perspective than most people in the camp. Each time authorities transferred me to a lower security level, I felt more layers of stress come off.

But even in the camp, I felt disappointed many times. For example, after St. Martin’s Press published my book Inside, newspapers began to publish reviews of the book. Staff members responded by locking me in handcuffs, sending me to the hole, and transferring me to another prison. That’s how I transferred from the camp in Florence to the camp in Lompoc.

While in Lompoc, I continued writing for publication. After 18 months, authorities at Lompoc Camp locked me in segregation again. The captain of the prison came to see me. The experience disrupted my life. Ironically, it opened career opportunities later.

Logically, I would have thought that administrators would support my efforts. By writing, I stayed away from problems. Simultaneously, I developed skills that would allow me to transition into society.

From the view of staff members, however, by writing for publication, I brought unwanted attention to the Bureau of Prisons. They made me pay the price, sending me to the hole or transferring me to prisons in other parts of the country. Over the course of the 9,500 days that I served, I spent time in prisons located in the following states: Florida / Georgia / Oklahoma / Arizona / Washington / Alabama / Pennsylvania / New Jersey / Colorado / California.

Each time authorities transferred me, I felt disappointed. Over time, I learned to build grit.


I learned from leaders who built great companies or leaders who overcame enormous struggles. They taught many lessons. From them, I realized that regardless of what administrators did, I would have to stay on my journey and prepare for success. Disappointment, I learned, would become a part of the prison experience. It’s a message I want to convey to the members of our community. Despite the decisions that others make, we must persevere. We must continue pushing forward to manifest the success that we want to build.

People who are in prison will face many challenges ahead. By the time this message comes, most will already be familiar with disappointment. Some possible examples:

Authorities chose to bring a criminal charge when a civil case may have been more appropriate.

Attorneys did not deliver what they promised.

Prosecutors may lie or misrepresent facts to get a conviction.

The sentence may not be fair.

Prison administrators may not do what they should.

Family and friends may disappoint.

These are the pains of confinement. But leaders know they must fight through disappointment, always striving for something better.

Recently, in preparation for my interview this week, I read through the Federal Register to better understand discrepancies between the intent of Congress and the activities of the BOP.

I came across a complaint from a US Representative. He complained to the BOP about the agency using a bad-faith effort to circumvent the will of Congress with the First Step Act. Initially, the BOP wanted to withhold Earned Time Credits. Good advocacy led to a change. Now, people receive earned time credits for the programs they complete, not for the number of hours that pass.

This example goes back to what I wrote many times before: disappointment is part of the prison journey. We must advocate, knowing the importance of perseverance.

During the 26 years that I served, I went through several extensive reform periods. As with all reform periods, the BOP would iterate policies over the years. It always caused disappointment, but I never stopped working toward a better outcome.

The First Step Act is the most significant prison-reform legislation since 1987. If people do not advocate for themselves, they can count on serving the entire sentence. The BOP is an agency that operates like any other bureaucracy. It seeks to grow. Yet the First Step Act provides mechanisms people can use to open the door. 

People must work to advocate for themselves at every stage, understanding the opportunity costs that accompany every decision.

It’s a lesson that I learned from leaders like Socrates. It’s a lesson that readers of this email likely practiced before the government targeted them for prosecution. It’s a lesson that every person in prison would be wise to practice now. Regardless of what disappointment comes, persevere. Work toward success.

I am very optimistic that when the new director gets her arms around the agency, we’ll see a positive implementation of the First Step Act. Yet I would also expect people in prison to feel many disappointments along the way.

I will do my best to gather the information that members of our community can use. And I will always work hard to prove worthy of your trust.

One thing I can tell everybody: I always kept hope during my 9,500 days in prison. The First Step Act didn’t exist when I served my sentence, which was one reason why I had to serve many years. 

People now have a mechanism to work toward a better outcome. But it’s work. And there is no guarantee of anything. Administrators may deny requests for administrative remedy. Keep looking forward. Don’t give up hope. 

When disappointment comes, work toward something better, regardless of what the agency does.

Earlier in this letter, I wrote about a captain locking me in the hole for writing books when I was in Lompoc. That captain became a warden and then a member of the BOP’s executive staff in Washington. After my release, we connected again. He opened opportunities that helped me to build a digital-product business that I’ve since turned into a nonprofit, hoping to make a more significant impact on the world.

I’m passionate about working toward prison reform and helping people in prison get the best possible outcome. I hope that every recipient of this letter will join this effort and stay focused, always working through the challenges and disappointments that come.


Michael Santos

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