08/21/2011 07:38 pm ET Updated Oct 21, 2011

How and Why I Teach in Prisons, Part Four

This is the fourth installment in a four-part series. Start the series here.

It is stories like Ray's that give me hope that there is a road back for these men whose lives have been spent in the torture of prison life. Perhaps as educators we can figure out a way to intervene ahead of time to prevent these tragedies from even occurring. It is a public discussion that would be important to have. Any overall strategy would need to deal with keeping kids in school by structuring the curriculum around topics they want to learn about -- such as entrepreneurship and making money, sales and marketing, inventions and business organization.

Although almost all the prisoners were self-employed before being incarcerated, they do not think of themselves as entrepreneurs. This is unfortunate, as it limits their ability to get out of the drug industry and start legitimate businesses. Much of my career has been spent on this very issue: helping low-income youth find a pathway to financial independence through small business start-ups.

With all the talk of school reform, seldom if any thought given to what the millions children that drop out of school every year want to learn. Years ago I met with one of America's top philanthropists and shared this idea of getting feedback from dropouts on what subjects they would like to study, and to then adjust the high school curriculum accordingly. His response? "Why would we do that? We know what they need to learn and we know how to teach it." He was wrong then and wrong now. His foundation spent many millions of dollars on school reform but ignored the issue of curriculum - and his efforts have had minimal results. It would seem to be a logical first step to ask those who are dropping out what would motivate them to stay in school.

Perhaps it is also time to redefine drug addiction as a health issue and treat it like an illness, thereby eliminating the hundreds of thousands of young lives that are being destroyed behind bars. As a nation we should have an ongoing discussion about decriminalizing the industry that has drawn so many young men and women into its clutches.

Joe Robinson, a hero, wanted to do something about this. Co-founding the entrepreneurship program at Sullivan with me, Joe came up with the acronym ITEM (Inmates Teaching Entrepreneurship and Mentoring). The first planning session was held on May 22, 2004.

Since the beginning, the program had been a success. Every year at least a dozen families competed in our family business plan competition. It was wonderful to see the different business ideas and their presentations by fathers and sons, mothers and daughters.

There was a plan for a van service to take families directly to the prison on visiting days; another for a soul food restaurant in Brooklyn, a cleaning service in the Bronx, a home-repair initiative in Queens. There were several tutoring businesses. All had ways to include more than one family member in the venture. After each presentation, the audience would clap and cheer. Every family got a Barnes and Noble gift certificate.

Sheila and I were at Sullivan for five hours with 50 inmates and their families on the day of our most recent visit. Because the inmates were putting on a play, the family business plan competition was canceled this year. As a result, I spent most of the day talking to the men about their life stories as a way to better understand what had caused the tragedies of their crimes and their incarceration.

The use of nicknames is important to our understanding -- each prisoner has a nickname: Diamond, Big man, Gigdog, Machete, Donkor(one who is humble), Eyeglass man etc etc. The prisoner's real name is referred to as the government name.

I ran into Jestina Bryan, a former student of mine from 1983 at Murry Bergtraum High School in New York. Her brother, Bruce, was an inmate. She had a role in the play, which was written by another prisoner, Dwight R. Delee. It was a brilliant scenario, with each actor in a cell constructed of masking tape. One by one, their loved ones came up to read actual letters that had been sent to them. The agony of receiving a Dear John letter was captured in the play by José Sanchez, who tearfully broke down upon reading one. There were tears in my eyes as Sheila and I drove back to New York. As we crossed the bridge over into Manhattan I thought of what one of the prisoners had said to me as we were leaving: "This program gives us faith."

Being involved in Joe and Sheila's ITEM program is one of the highlights of my teaching career. It should be replicated in the prisons of the world. Imagine how many prisoners' lives would improve.