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 5-Success after Prison 

Picture of Michael Santos

Michael Santos

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After 25 years in prison, I transfer to a halfway house to serve my final year with the Bureau of Prisons. The decisions at the start of the sentence influenced the liberty I had at the end.

The Halfway House after Prison:

People assigned to the dorm of the Atwater camp were still sleeping when I woke on August 12, 2012. Over the past several years, I adjusted my daily routine to wake when others slept and to sleep while others ran around the housing unit. I used earplugs to block the noise and a mask to cover my eyes. By 3:00 a.m., I pushed myself through my last exercise session from inside a federal prison, wondering how my life would change after I walked out. 

I had 9,135 days of imprisonment behind me, just over 25 years. At 9:00 a.m., Carole would drive to the prison, and together we’d drive to the halfway house in the Tenderloin District of downtown San Francisco. My case manager recommended me for the maximum placement I could receive in a Residential Reentry Center. I appreciated the privilege of serving the final 365 days of my sentence in the halfway house.

After my exercise, I walked around the track alone, reflecting on the entire journey and all I learned. I went to the chapel and prayed for guidance. I knew the world had changed in many ways since I started serving my sentence, but I felt ready. 

In truth, I felt as prepared as I ever would have been after I served eight years in prison. By then, I had a master’s degree and knew I would never violate a law again. Since mechanisms didn’t exist to advance my release date, I would have to climb through 16 more years. As I sat in that chapel waiting, I thanked God for protecting me through the journey and for my many blessings, especially Carole.

Finally, an announcement over the loudspeaker instructed me to report to the rear gate. 

I walked through gates that separated the minimum-security camp from the penitentiary. Officers escorted me to the discharge area and began to process me. A staff member handed me a few hundred dollars in cash from my account and indicated that I’d receive a check for the remainder. 

That was it. I walked outside and met Carole. She wore a yellow dress with a yellow ribbon tied around her waist. With tears of joy in her eyes, she hugged me, and we drove off to start our journey together.

Although we were together for the first time, we weren’t free. The case manager told me that I would have to report to the San Francisco Halfway House within three hours of my release. Carole showed me a map indicating that the drive would take three hours, so we didn’t have time for diversions. 

We wanted to be together, of course. The time crunch, however, dictated that we needed to get on the road. I had heard from others that if I didn’t get to the halfway house in time, the case manager would deny my request for home visits for several weeks. To avoid that complication, we resisted the urge to stop for alone time, and we drove straight to the halfway house.

Once we got into the car and buckled in, Carole passed me an iPhone. Smartphones didn’t exist when I started my sentence. I’d seen phones on television, but I had never held one. I put the phone to my ear. Since I didn’t hear a dial tone, I thought the phone didn’t work, even though I saw the lighted face with all the apps. She laughed as she showed me how to use it. Before that day, I’d never sent an email, watched a YouTube video, or accessed the internet. 

Technology fascinated me, even though I didn’t know how to use it.

While in prison, I frequently dreamed about the internet, wondering how to use it as a tool or how it would contribute to my career. I read many books and articles to learn about the power of the web and even leveraged my relationships to participate indirectly.

Since the late 1990s, I have had a web presence. I persuaded people in my support network to build websites for me. They published my articles, and they’d send images that showed how my website looked to visitors of 

But there wasn’t any real way to experience the web without computer access. Reading about the internet seemed about as authentic as reading about playing tennis. But without getting online, I didn’t know how to appreciate the power of technology fully. When Carole gave me an iPhone, I got my first chance. As she drove, I played around with the phone, calling family and friends.

Carole and I spoke about our plans. Goals carried me through the 25 years inside, and I pledged to continue living a values-based, goal-oriented life. During my final year in the halfway house, I vowed to sow seeds that would allow us to start my career. I intended to:

  • Create products and services that would improve outcomes for people in the criminal justice system.
  • Create a business model to help more formerly incarcerated people transition into the job market.
  • Create campaigns that would spread awareness of why reforming our criminal justice system made sense. I wanted to think innovatively in ways that would inspire more people to pursue paths that would lead to success upon release.
  • Create multiple revenue streams that would build stability for Carole and me.

But first things first. During my year in the halfway house, I needed to establish myself. 

Fortunately, I had begun making plans long before I left prison. I had job opportunities waiting. I had money in the bank. I had an extensive support network. Further, I had a product line to launch with the different books I wrote while serving my sentence. My books included:

  • Inside: Life Behind Bars in America
  • Earning Freedom: Conquering a 45-Year Prison Term
  • Prison! My 8,344th Day
  • Triumph! The Straight-A Guide For Conquering Imprisonment and Preparing for Reentry
  • Success! The Straight-A Guide for At-Risk Youth
  • Profiles from Prison
  • About Prison

I wouldn’t describe the books I wrote as masterpieces of English literature. Instead, they served a purpose: to help people understand prisons, the people they hold, and strategies for growing through prison successfully. 

I hoped my books would lead to credibility as I ventured into the world to start my career. I intended to use the books as tools, resources I could leverage to build a business or income streams. 

My friend and business partner, Justin, also provided a lot of help. Justin had built a consulting business, using the lessons I wrote when we were serving our sentences. People going into the system could use those lessons to get a better outcome, and Justin provided one-on-one consulting services. I created a head start by working with Justin to launch that business while I was still in prison. The week I got out, I had income opportunities by ghostwriting books for others.

Experienced convinced me that anyone could use deliberate strategies to reject negativity or overcome challenges. That universal message applies to anyone and everyone. If deliberate strategies could empower me through decades in prison, others could also use them to achieve more.

People going into the system, or those serving time, should contemplate steps they can begin taking now. Regardless of external circumstances, I learned that options always existed. Regardless of what rules govern our lives at present, we can work to build skills that will influence the people we’re going to meet and the opportunities that will open for us. We may not be able to change our current predicament, but we can always work to change ourselves.

Halfway to Liberty

I’ll never forget my thoughts as Carole drove me across the Bay Bridge, taking us from Richmond to San Francisco. The majestic skyline inspired me. I felt so good to be in a major American city.

Carole dropped me off in front of the halfway house, and the staff buzzed me inside. I didn’t have any trouble navigating the rules. After decades in federal prison, everything seemed easy. The intake officer assigned me to a two-person room, but my roommate wasn’t there. I sat in a chair and began experimenting with the iPhone, connecting with the world. 

Although I got to the halfway house on a Monday, my case manager, Charles, didn’t meet with me until Thursday. While doing his intake paperwork, Charles commented on the length of time that I’d served. He suggested that I participate in counseling sessions to help me acclimate.

Before going to that meeting, I prepared for such a recommendation by gathering:

  • Books I wrote, 
  • Support letters I’d received, 
  • Curriculum vitae that listed my published writings, and 
  • Job offer from an employer confirming that I could start working as soon as the halfway house authorized me to begin. 

“How did you get all this done while you were in prison?” He did not expect to see so many resources from someone who served 25 years.

As Charles flipped through the books, I could sense how the tangible work I presented influenced his perception. Instead of seeing me as the ex-convict who served a quarter century and needed counseling, he treated me as a man. The case manager said he would give me as much liberty as his position authorized. When he excused me from having to waste time in the counseling classes, I felt relieved. In an instant, I had credibility with him, and to the extent he was able, Charles agreed to assist with the plan I laid out for my first year in society.

That initial meeting with Charles went well. Without a doubt, I felt fortunate to have him as my case manager, as I know it could have gone differently. Had I not brought those tangible resources with me, I would have had to waste hours going through several classes before I would qualify for work release. He treated me with dignity as if we were two men rather than as if I were an inferior human being just released from prison. 


The roots for that successful meeting extended way back to the 1980s when I waited for sentencing from inside the special housing unit of the Pierce County Jail. 


While in my cell, I read about Socrates. From his story, I learned the importance of living for something greater than myself. Instead of dwelling on the challenges of my decisions, I could empower myself by thinking about others. Through Socratic questioning, I could learn the relationship between my decisions and how others would perceive me. 

With that insight, I began contemplating people like Charles—case managers and probation officers—before my judge even imposed my 45-year sentence. They were my avatars. I could create plans to influence their perceptions by thinking about what they would expect. 

I believed I could influence a better outcome upon release by executing those plans every day of my sentence. Those plans gave me hope and helped me to restore confidence—as if I could control some aspect of my life.

Still, I felt fortunate to have a case manager who treated me well.

Some readers may be familiar with the social scientist Abraham Maslow and his theory about the hierarchy of needs. Maslow wrote that we could not reach our highest potential unless we first satisfied our basic needs. For example, to appreciate the value of education or art, we first need to make sure we have basic needs like food, clothing, and shelter. The same principle would apply to my adjustment in society. 

I needed identification to make a complete adjustment after a quarter century of confinement. For the past month, I’d been studying a handbook from the Department of Motor Vehicles, and I asked Charles for permission to go to the Department of Motor Vehicles. I wanted to register for the driving test.

He granted my first pass for three hours, allowing me to walk to the DMV.

Self-Directed Questions:

  • What strategy have you put in place to influence your transition from prison to society?
  • What will your case manager think about you the day you transition to a halfway house?
  • What can you begin doing today to influence the level of liberty your case manager will grant?

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