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The below lesson is an excerpt from my upcoming book, When Not If: A CEO's Guide to Overcoming Adversity, Forbes Book, January 2024.

Intellectually, I had been thrown into a world in which my prior education and training provided zero preparation. Federal criminal law might as well have been written in a foreign language for me. I knew I would have to devour every book obtainable, and that trial and error would be my only path. I took a job as a prison law library clerk at FCI Fort Dix earning 16 cents per hour plus a rudimentary legal education. As I educated myself, I agreed to help every inmate who would accept my inexperienced but earnest assistance. I mastered law practice with a No. 2 pencil and manual typewriter.

One way I improved intellectually was by gradually becoming a decent jailhouse lawyer. Any time an inmate wants something to happen, it generally requires the preparation and filing of a motion. Fortunately, this can be done with, or without, the assistance of an attorney. Unfortunately, even when a nonlawyer inmate files this type of paperwork with the court without counsel, they must follow the same format and abide by the same rules that real lawyers are required to follow. If there’s anything amiss, the motion is rejected.

Eventually through trial and error, I learned the rules and filed hundreds of pro se motions with the court. When my fellow prisoners protested that I was wasting my time, I exploded, saying, “Are you crazy? It’s my only hope!” I had long given up hope that outside lawyers would or could help me.

Of course, the other inmates knew something my ignorance protected me from knowing. They were convinced there was, basically, a zero-percent chance of the court approving any motion filed by an inmate, or attorney for that matter. Their belief was continually confirmed by the nearly 100 percent failure rate. Not knowing how hopeless it was, I dove in and started filing everything possible.

On behalf of my fellow inmates and myself, I kept notes on the extremely low percentage of cases that were successfully reversed. I kept statistics on different elements of courtroom procedure. I journaled every tactic and strategy I thought might help them and myself. Just as in business when I attempted to be the smartest guy in the room, I wanted to become the smartest jailhouse lawyer in order to help as many people as possible, knowing that as I was helping other inmates, I was preparing to better represent myself.

I discovered most attorneys used templates, cut-and-pasted the same arguments from the other hundreds of cases they were handling contemporaneously. I learned how to use patterns that had been effective in other cases. I would periodically achieve a small victory.

The Puerto Rican Latin Kings brought me Jose’s letter from his attorney stating he did not qualify for the recent drug-2 reduction enacted by the Sentencing Commission. With a little research, I thought he had a chance, so we filed the motion and four months later we learned the court accepted our argument and reduced his sentence by three years. The Puerto Ricans always paid for services in white lightening, a moonshine derivative tasting worse than anything you can imagine.

I was never much of a fiction reader, so as part of my determination to improve intellectually at the rate of 1-percent per day, I made the decision to read a new book every few days. Luckily, the prison library had a collection of classic literature. Coming out of the engineering environment of the Air Force Academy, my knowledge of the classics was woeful. I knew this would likely be my only opportunity in life to remedy this failing. I read, and incredibly enjoyed, dozens of literary classics, and this escapism saved my sanity and helped me not become too hardened during this ordeal.

In a strange way, I am extremely grateful for this opportunity which I knew never would have happened unless I went through this challenge - a theme I would learn over and over before this adventure was complete.

LESSON: For overcoming adversity, early on I realized I must immerse myself in intellectual development and education in order to control my own destiny. I could not rely on attorneys, accountants, or industry experts to have the knowledge. I would have to find intellectual paths less traveled to be victorious.

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