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Prison Professors

May 5, 2022

Earning Freedom: Conquering a 45-Year Prison Term by Michael Santos


Chapter 15.3


     It’s Wednesday, April 18, 2012 and I received the most amazing book during mail call.  It’s so impressive, The Oxford Handbook of Sentencing and Corrections, edited by Professor Joan Petersilia, who is the Adelbert H. Sweet Professor of Law at Stanford Law School, and Kevin R. Reitz, who is the James Annenberg La Vea Professor of Criminal Procedure at the University of Minnesota Law School.  The 764-page book includes contributions from many authors who wrote individual chapters on various subjects pertaining to sentencing and corrections in America’s massive prison system.  My face beams with pride when I turn to chapter 25 and I see the words I wrote more than three years ago, describing the life I’ve lived since 1987.

I don’t know how to describe the honor I feel that Professor Petersilia invited me to write about my experiences.  I’m a prisoner, after all, and yet by including my work I’m in the company of some of the world’s leading scholars who hold distinguished positions in some of the world’s leading universities.  To show my appreciation, I will read each chapter and publish a review to describe what I learned from those who contributed.

There isn’t anyone here with whom I can share my joy, but inside, I feel a liberating gratification, giving me a sense that some meaning has come from this long journey.  It’s a journey that is coming to an end, as I have news that I’m scheduled to transition from the Atwater federal prison camp to the San Francisco halfway house on August 13, 2012.


It’s July 1, 2012, the last full month that I’m going to serve in federal prison.  I have 9,091 days of prison behind me, only 44 days of prison ahead.  From the beginning I’ve been exercising very hard, but I’ve been waiting for this month for decades, always intending to exercise harder during my final month than ever before.  After all, it’s the last full month in my life that I’ll have to focus exclusively on exercise.  I’m determined to run 500 miles during the month.  In addition, I’ll do 10,000 pushups and 4,000 dips. The intense workout will quell this steady surge of anticipation that has been building for months.

Carole has already made the move to Lee’s guesthouse and she secured a job at a Bay area hospital.  As crazy as it may sound, I know that my life is one of many blessings, but more than anything else, I cherish the relationship I’ve built with my wife.  We’re both indescribably excited about the prospects of building our lives together.  Despite the love, enthusiasm, and anticipation inside of me, however, I have a measure of anxiety as well.

For 25 years I’ve been a prisoner, living in the midst of men, strangers.  Privacy has not been a part of my life.  I don’t know how to eat with metal silverware or off of ceramic plates.  I’ve not had a drink from a glass since 1987, nor have I taken a shower without wearing flip-flops.  We’re in our 10th year of marriage, but my wife and I have only known each other under the bright lights of prison visiting rooms, always under the watchful eyes of vigilant prison guards.

I don’t have any idea about the magnitude of change that is about to come my way, but I know that it’s coming.  Running these long distances helps to dissipate the anxiety, but I can’t help thinking about how I’ll react to the changes that are about to come.  I don’t worry about earning a living or financial matters, as I’ve prepared well for those challenges.

My anxieties are of a more primal nature.  For instance, I dwell for hours at a time about how I’m going to muster the courage to poop in front of my wife.  Will she kick me out of bed if she hears me pass gas?  I don’t have any idea on how I’m going to handle these complexities of domesticity, but I know that I can count on Carole to help me.  She just doesn’t yet know the worries that I have.

I wonder what’s going through her mind.  For years she’s lived as a prisoner’s wife, with visiting rooms being our living room, bedroom, and kitchen.  She has been very protective of her time with me, and yet it has been only an abbreviated time.  Now, in a matter of days, all of that will change. 

Carole has begun making purchases to ease my initial transition.  She bought us matching iPhones, clothing and hygiene supplies that I’m going to need.  We’re coordinating events with family, as my sisters, mother, and grandmother want to visit.  They’ve been waiting for 25 years to welcome me home, but my release is complicated by three factors:


  • I’m being released to San Francisco and my family lives in other cities;


  • I’m not really going home, but to a halfway house; and



  • I don’t know what restrictions the halfway house is going to place on me.


With all of those complications, I’m asking my mom and sisters to let me spend the initial weeks with Carole.  Before receiving visits, I need to settle with her and understand more about this transition into society and what it truly means to live as a husband.  I want to receive my driver’s license, to begin reporting to work, and to complete whatever demands the halfway house makes upon residents as a condition of increased liberties.  I expect that I’ll need 90 days to settle.




It’s 2:00 am on Monday, August 13, 2012.  Today is the day, the 9,135th day that I’m waking on a prison rack.  It’s also the last.  I climb down and dress in my exercise gear.  I take my cup of instant coffee and walk into the center of the housing unit, where I sit alone in the dark.  It’s been 25 years and two days since my arrest, and in a few short hours I’m scheduled to walk outside of these fences.  Why, I wonder, does society equate this particular amount of time with the concept of justice?  In what ways did the quarter century I served contribute to community safety?

As I look around and see all the other prisoners sleeping, the only answer I can come up with is that society wanted to punish me for the laws I broke when I was in my early 20s. I’m now 48 and I don’t even remember much about those crimes, as the length of time that I served gradually squeezed those details out of my memory and consciousness.  The punishment felt severe with my arrest and trial and sentencing.  But as the weeks turned into months, and the months turned into years, I turned all of my attention toward those three principled steps that were going to guide me through my journey:


  • I made a commitment to educate myself;
  • I made a commitment to contribute to society in measurable ways; and
  • I made a commitment to build a strong support network.


That strategy, I hoped, would help redeem the bad decisions of my reckless youth and help me reconcile with society.  As the years passed, however, I lost sight of the fact that society was punishing me. Prison became the only life that I knew. Is a man still being punished if he doesn’t even know it?

     By the time I earned my master’s degree in 1995, I felt as ready to live as a contributing member of society as I ever would.  That was 17 years ago, but our system of justice didn’t have a mechanism in place to encourage individuals to work toward earning freedom. As Shakespeare suggested in his play A Merchant from Venice, the system wanted its pound of flesh.  Regardless of what efforts an individual made to atone, in our system of justice, all that mattered was the turning of a sufficient number of calendar pages.

As of today, 300 calendar pages have turned since my initial arrest.  And in a few more hours, I’m going to walk outside of these gates, where I’ll see Carole waiting.

It’s 4:00 am and I begin my exercise, first with strength training, knocking out 50 sets of pushups.  Then I begin my run.  In July I set a goal of running 500 miles.  With focus and persistence I blasted through that goal, hitting 700 miles that included eight back-to-back marathons during the month. 

I’ve now exercised for 1,340 days without a single day of rest, but what new routines will begin tomorrow?  Many years ago I read What Got You Here Won’t Get You There, a book by Marshall Goldsmith, a business strategist. The book made an impression on me then, and it seems particularly relevant to me now, as I finish running my 12th and final mile around a prison track.  I’m opening my mind to the reality that I’m going to have to change the rigid and precise tactics that have carried me through prison.  But I’ll never relinquish my commitment to living a principled, deliberate, strategic life.  I don’t know how I’m going to have to change, but I’m open to the changes that will come when I walk outside of these prison gates.




It’s 7:00 am and I’m walking alone, steadying my thoughts.  I tried to use the telephone but my account has been disabled, confirming that my time in prison is ending.  I see a long line of men waiting to enter the chow hall for breakfast and I feel the many eyes upon me; I feel their energy, good wishes from them, but I need this time alone.  I walk into the chapel for solitude and I pray in gratitude, thanking God for protecting me through the journey, asking for guidance as I take the next steps home.

“Michael Santos,” I hear the announcement.  “Number 16377-004.  Report with all your property to the rear gate.”

I’m carrying my copy of The Oxford Handbook of Sentencing and Corrections, but I’ve given everything else away.  I leave the camp and walk toward the gate at the rear of the penitentiary.  A guard comes toward me from inside the gate and he crosses through.  He calls me forward and asks a few questions to confirm my identity, and it’s as simple as that. 

We walk through a processing area and I see that it’s 8:48, which is coincidentally the same number as the criminal code for the crime I committed.  Another guard fingerprints and photographs me.  Two other guards ask me more questions to confirm my identity.  And that’s it.  We walk through penitentiary corridors, and across an area that leads me into a lobby.

I turn right around a corner, where I meet other guards.  They hand over funds from my commissary account and authorize me to cross over to the other side, where Carole, my lovely wife waits, her elbows to her side, tears flowing down her cheeks, prayer hands pressed close to her mouth as she stares in disbelief as I walk out of the penitentiary and into the embrace of her arms.

At last, at last.








When we walk out, Carole hands me an iPhone. I’d never seen a smart phone before. When I put the device next to my ear, I didn’t hear a dial tone.


“It’s not working,” I told her.


Carole laughed.


The world had changed during the 9,135 days that I’d been a prisoner. Although I’d read about technology, I hadn’t ever sent an email. Although I had a website since the dawn of the Internet, I’d never accessed the Internet. I’d never made a YouTube video, or used any of the technology that the world took for granted.


I intended to learn.


I sat in the passenger seat as Carole drove me from the prison in Atwater to a halfway house in San Francisco. We had more privacy on that drive than we’d ever had during our first 10 years of marriage. It was the first time we sat together outside of a guard’s presence. And yet rules limited our time together. If I didn’t make it to the halfway house within the three-hour timeframe I’d been given, I’d begin my time in there on the wrong foot.


Carole drove steadily while I feasted on a pizza she brought me.


When we came out of the Central Valley and crossed the Bay Bridge, I saw the San Francisco Skyline.


“Within five years,” I told Carole, “I’ll build my first $1 million in assets.”


Carole shook her head. By then she understood my ambition, my quest to overcome obstacles. “You need to relax, take a breath. Get to know the world.”


“It’s go time,” I told her. “For 25 years I’ve been held down. I’m ready. We’re ready. I’ll work harder out here than I’ve ever worked before. We’ll figure it out together. I can’t wait for life to unfold. We’ve got to make life happen.”


I settled into the halfway house and immediately began working. As I had learned in prison, I would need a deliberate, disciplined strategy to grow.


Step 1: Define success

Step 2: Create a plan

Step 3: Set priorities

Step 4: Execute the plan


As in prison, I adhered to the same principle of moving forward toward my goal with a 100% commitment. First step would be to get a driver’s license. I needed to be mobile. Then, I had to consider strengths and weaknesses.


With regard to strengths, I had a positive mindset. I understood that I had faced the challenge of a quarter century in prison. Yet as planned, I returned strong, with my dignity intact. I could leverage that strength to carve out new opportunities.


But I also understood my weaknesses. As a result of prolonged imprisonment, I’d never held a job, never built a workforce or managed employees. My strength was in a strong work ethic, being self-directed, and being relentless in pursuit of my goals. I had to leverage those strengths, turn them into assets that would become more valuable over time. I used my time in the halfway house to the best of my ability, investing hours to learn how to use technology, to understand the Internet.


The economy was still weak in August of 2012. Our country had been in a deep recession for several years. With my liberty, it all felt right. Unbridled optimism blinded me to risks. I believed the economy would improve, and I wanted to participate. In my mind, the best way to participate would be to acquire appreciating assets.


During those first days in the halfway house, I began engineering a plan to make my first real estate acquisition. Despite having a zero-zero-zero credit score, I persuaded a successful real estate developer to provide 100% financing on the purchase of a new house in the San Francisco Bay area. I hadn’t been in the halfway house for a full month when I had a deal under contract. That deal would become the start of many others.


Preparations from prison resulted in scores of opportunities opening. By the time I finished with the halfway house, and with the Bureau of Prisons, after 9,500 days, San Francisco State University offered me a position to become an adjunct professor. With permission from my probation officer, I traveled across the United States to lecture in universities.


Sponsorship from the California Wellness Foundation allowed me to develop a curriculum to teach the values-based, goal-oriented strategies that I learned from other leaders. Together with my partner, Justin Paperny, we distributed those concepts to jails, prisons, and schools across America.


Such lessons prepared me for success through struggle. To the extent that others adhered to those same principles, I felt confident they too would thrive. For centuries, leaders had been living in accordance with self-directed plans:


Define success

Set clear goals

Move forward with a 100% commitment to success

Visualize the outcome

Take the incremental action steps

Create accountability metrics

Be aware of opportunities

Live authentically and honestly

Celebrate incremental achievements

Show appreciations for the blessings in life


By documenting those strategies that I learned from leaders, opportunities opened. As a direct result of the seeds that I sowed during imprisonment, I could persuade other people to believe in me. I would challenge business leaders to use their discretion and invest with me. They could look upon the record I built. By staying focused and disciplined while growing through a quarter century in prison, I argued that I was well prepared to prosper in society. Rather than judging me as a man with a zero-zero-zero credit score, I invited them to support efforts I would make to build, grow, and contribute to the making of a better society. That strategy paid off. Within five years of the conclusion of my sentence, by August of 2018, I controlled more than $5 million in assets, and built equity of more than $3 million.


Then, a lawsuit from an agency of the federal government resulted in the loss of all those assets.


For that story, how I litigated through it, and how I worked to recover and build millions more, you’ll need to get the next book—which I’m writing now. Visit for an update.


The one promise I make is that I’ll never ask anyone to do anything that I haven’t done, or that I’m not doing. Regardless of what businesses or opportunities I create, I intend to continue creating resources to teach and inspire people in jails and prisons. We all must live in the world as it exists. That means we must accept that problems will surface as a result of our criminal backgrounds. We must succeed anyway.


By living the values-based, goal-oriented strategy that I learned from leaders, I’m paying it forward, trying to prove worthy of the guidance and inspiration I got from Socrates. His wisdom inspired me while I was still locked in the Pierce County Jail, before a judge sentenced me to 45 years. Since then, I’ve been striving to “be the change that I want to see in the world,” just as Gandhi advised us all to live.


Stay focused, stay deliberate.


Earn freedom!

May 1, 2020