After spending over twenty years building a successful business from scratch, I decided I wanted to teach. I planned to take what I had learned from my business experience and share it with those who wanted to do the same. I was in my early fifties and had no teaching experience, but I thought my education and business success would be more than adequate to land a teaching job at a nearby community college. I sent off hundreds of applications, which were met with complete silence by my potential employers.

I had learned years ago that if you want something in this world, you just have to keep after it until you get it, so I wasn’t going to give up on my teaching aspiration that easily. I went back to school and got a community college teaching certificate. I emailed another hundred or so resumes and waited for the schools to start fighting over me. It never happened. I spent another two-and-a-half years earning a marketing management certificate from Harvard Extension University thinking that would add some “pop” to my resume. But, still, no educational organization showed any interest.

My persistence finally paid off when, one day, I was offered a position to teach entrepreneurship at, of all places, a minimum-security prison camp. I had never been in a prison before, and teaching in one was not exactly what I had envisioned all those years ago when I decided I wanted to be an educator. There was no way I was going to turn the job down, though. I was sure it was this or nothing, so I wholeheartedly thanked the nearby community college for the opportunity. I had only a few weeks to create a class outline and enough material to get me through the first few classes. But I felt ready when my first day as a teacher finally arrived.

I’m a Teacher, Now What?

I walked through the guardhouse on my first day as a teacher and waited for the guard to search my book bag. I strode cautiously through the prison yard, walked up the concrete steps to the dayroom that would be my classroom for the next few hours and waited for my students to arrive. As a way of introducing myself to my first class, I told them, “I’ve never taught a class before, and I’ve never been in a prison before, so it’s safe to say I’m going to learn a lot more from you over the next eleven weeks than you could possibly learn from me.”

Upon hearing that, a few of the inmates exchanged looks of bewilderment. What I didn’t realize at that moment was that my time in prison was going to dismantle a lot of stereotypes for both me and my students. Any notions my students might’ve had that teachers were know-it-alls who focused on delivering lessons they’d later test on for the sole purpose of assigning a letter grade would soon, hopefully, be eradicated. Likewise, my preconceived notion of prison inmates as lost causes who were getting the punishment they deserved would also soon be radically changed.

One of the students I encountered early in my teaching career was named Michael. Michael was a man in his early sixties, small in stature with greying hair and an icy stare. He walked into the dayroom like a man with a purpose and he was quick to speak up on our first day of class as I introduced myself to my ten new students. “What can you do about getting some brewed coffee in here? All we can get is instant,” he said. I liked Michael right away.

“I didn’t do what I’m in here for,” Michael continued. “The arrested me for drug possession, but it wasn’t my stuff. I was a bad ass when I was young, though, and I’ve got two felonies on my record to show for it.” The class was giving him the floor so Michael continued, “I’ve lived a clean life for over twenty years. I left a five bedroom house and grandchildren to be here, but my attorney told me, with my record, I had better take the deal. A black man with two felony convictions can’t get a fair trial in this country no matter if he’s guilty or not.” No one in the dayroom showed any sort of objection to what Michael had to say.

What I Learned From Teaching

The opportunity to teach in prison had provided me with a view into a place that is hidden away from the public and I learned a lot in my time there. Statistics show that Michael is not alone in his predicament. According to the Department of Justice’s Bureau of Justice Assistance, “The overwhelming majority (90 to 95 percent) of legal cases result in plea bargaining.” The preponderance of plea bargaining takes the strain off of the court dockets and keeps the criminal justice system moving forward efficiently and it also provides guys like Michael with two really bad choices: take the deal and the shorter sentence or roll the dice and stand in front of a jury and risk going away for a long time.

Of all crimes committed, drug crimes account for the most plea deals. According to the National Registry of Exonerations drug crimes compromise forty percent of all guilty plea cases and sixty six percent of people convicted of drug crimes that were later proven to be innocent originally pleaded guilty to avoid the risk of being found guilty by a judge or jury.

Michael was obviously well-educated and initially expressed an interest in buying and selling real estate when he got out. He started the class with a lot of enthusiasm, and started a business plan for a property management company. I watched powerlessly as Michael seemed to lose interest as the class progressed. I can’t imagine it being easy to transition to prison in your sixties, sleeping on the metal bunks and eating prison food when you have had it so much better for the past two decades. My guess is that his prison experience wore him down.

Michael stopped contributing and turning in homework about halfway through the class. My attempts to draw him out were fruitless, he mostly sat at his table with a stern and sullen look on his face. I saw him a few months after his class graduated on my way out the front gate and I almost didn’t recognize him, he had lost a lot of weight and looked sort of lost. “My family’s not doing too good without me being there” he explained, we’re gonna lose the house it looks like”.

I remember Michael not because his circumstances were unusual, I met many more in similar situations, those who had been given no real choice except to take whatever plea deal their lawyer could arrange whether they had committed the crime they were charged with or not. It streamlines the system when people who are charged with crimes don’t tie up the court system. But is the process that leaves the innocent no choice but to plead guilty a fair one? It’s easy to paint all offenders with a broad brush and think that they are getting the punishment they deserve for the crimes they committed. It’s easy until you meet a guy like Michael.

John K. McLaughlin is the author of Lifeline to a Soul. He spent half his life bootstrapping his start-up business as an industry leader. His desire to teach what he spent his career learning led him on a remarkable journey through the gates of a minimum-security prison where he taught entrepreneurship for almost three years. John has an MBA, a teaching certificate, and a marketing management certificate from Harvard Extension University. You can learn more about John’s current teaching program and his book here.

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