Unsolicited Letters

When serving decades in prison, I learned how to build powerful influences that could advance my preparations for success–as I defined success. I served my term before The First Step Act, so fewer mechanisms existed for people to work toward an earlier release date. Yet that didn’t stop me from trying. 

As I wrote in my book Earning Freedom: Conquering a 45-Year Prison Term, I began preparations for success early, with incremental steps. Each step adhered to my tri-part plan that would:

1. Focus on earning academic credentials and developing skills,
2. Show how I worked to make amends by contributing to society in meaningful, measurabel ways, and
3. Advance possibilities of building a stronger support network.

That plan advanced significantly during my fifth year of incarceration. By then I had earned a bachelor’s degree from Mercer University, and I was beginning work that would lead to a master’s degree from Hofstra University.

I read a provocative op-ed in The Wall Street Journal titled “Let ‘em Rot” by Professor John DiIulio, then of Princeton University. In his article, he argued that society should invest in building more prisons, not rehabilitation. He coined the phrase “super predator,” warning of a rising generation of criminals that would need to be caged preemptively.

I disagreed with the premise of that article.

As a person serving a lengthy sentence, I believed that society could get better results by encouraging people to work toward preparing for success upon release. I believed in people. I believed we could do better by investing more resources in education, opportunity, and hope.

So I wrote him a letter.

I didn’t know John DiIulio. I had never even set foot on a university campus. But in the dictionary available to me, I found Princeton University’s address. I wrote the letter by hand, expressing my respectful disagreement and laying out my vision for a better system. Instead of measuring justice by how many calendar pages turned with a person in prison, I suggested that we should incentivize a pursuit of excellence. 

Investing in human potential, I argued, would yield better returns for society than warehousing people.

I didn’t have any way of knowing whether the letter would reach him, or whether Professor DiIulio would respond.

At the time, I saw writing letters as a numbers game. I wrote hundreds, knowing full well that most people would not read or respond to a letter that originated from a federal prison. But if there was a better-than-zero chance of connecting with someone who could advance my prospects for success upon release, I made the effort. I was glad that Professor DiIulio chose to respond.

From Dialogue to Relationship

His reply surprised me: not only did he acknowledge my points, he agreed with many of them. He admitted the limitations of expressing nuance in a short op-ed and offered to send me his books for further discussion. 

Professor DiIulio invited me to continue the conversation, and his interest gave me hope.

Eventually, after I transferred to a medium-security facility, I learned that the warden knew Professor DiIulio personally. That relationship led to one of the most meaningful experiences of my prison term: hosting DiIulio and a class of Princeton students inside the prison. I gave them a tour, facilitated a full-day seminar in the warden’s conference room, and showed them a different side of the system.

That was year eight of my prison journey.

How To Succeed in Prison

Some people look at my story and say, “Well, you’re different. Most people wouldn’t be able to do what you did.” 

I never viewed life from that limited perspective.

I began my path through prison in solitary confinement. While there, in “the hole,” I learned how to think differently. People like Socrates, Nelson Mandela, and Frederick Douglass inspired me. Each of those men trained themselves to live productively while in confinement.

Change begins with a vision. I always visualized how I wanted to emerge from prison. I wanted to build a life of meaning, and I knew that to change the system, I had to build relationships with the people who influence it. Socrates taught me how to think about those people, and engineer pathways that would open more opportunities to bring influencers into my life.

Build the Machine

What I’ve learned — and what we now teach at Prison Professors — is that every person in the system can build their own machine. Anyone can work toward a meaningful plan that will accelerate the path to success, to better outcomes. It takes discipline, grit, and commitment. 

Progress is slow at first, like the “flywheel” Jim Collins describes in Good to Great. Once a person gets that flywhell moving, momentum builds. It accelerates. Over time, small steps compound into something meaningful.

The Lesson: Never Stop Reaching

The letter to John DiIulio was just one of hundreds I wrote. But every letter was part of the larger process: to prepare, to connect, to grow. In time, I opened relationships with many influential people, and they had an enormous role in the successful journey through prison, and upon release.

And that's the message I want to share: no matter where you start, you can always build something better. It takes vision, consistency, and the willingness to believe in yourself — even when no one else does.

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