They say that wisdom comes from experience and that experience comes from making bad decisions. Oak Park resident Stephen Jackson didn’t come up with that line, but he could sure say “amen” to it.

Jackson’s parents moved the family to Oak Park from the West Side in 1991 to provide better education for their children, but young Stephen didn’t fit the program at Oak Park and River Forest High School. He said, “I was invisible in the high school unless I did something and got in trouble. That got me some attention.”

However, he does not blame his environment for the path he walked down and acknowledged that he made several bad decisions as a young man. “I wasn’t a super hard core gang banger” he said, “but I was getting affiliated because it was the cool thing to do.” One bad decision led to another until he committed armed robbery and then spent 12 years in prison.

Now he works in Youth Services for Oak Park Township and provides mentoring to young students, mainly African Americans, at OPRF.

What transformed Jackson’s bad decisions into experiences which led to wisdom was how he used those years in jail. First, he had the good sense to listen to the advice he was given. He said, “My middle sister Pamela told me ‘I didn’t put you there, you did.’ That was one pivotal moment that was sobering. Things started shifting.”

He started journaling as a form of therapy and put up a sign in his cell, “Writing is my only shot at liberty.”

“One guy who was also in prison,” he said, “was the highest member of the gang I was part of. He called me into his cell one day and told me he wished he could be me, to be young and not have the responsibility of so many gang members under him. He told me to go to school, and if I had any problems while incarcerated to come to him.”

“I sort of had a blessing,” said Jackson. “He was a mentor in a way.”

Jackson followed the advice and went to school while in prison, earning two associates degrees, one in electronics technology and the other in computer drafting.

“Another moment was when I met a guy named Barnett Carney.” said Jackson. “That was the most pivotal moment. He was a black guy who knew Spanish so well he was playing Spanish Scrabble. I thought ‘that’s amazing.’ It was sobering to see the intellect of this guy from the South Side who was younger than me and to have someone who accepted me for who I was and call me out on my stuff.”

Inspired in part by Carney, Jackson learned to speak Spanish by watching Spanish language TV, taking a Spanish as a second language class and talking with Spanish speakers. He started a book club, a spoken word club and a yoga club.

Jackson said that religion was also part of his transformation. “I looked at every religion, that is I took something from every religion and applied it to my life. Religion definitely played a part.”

“Religion is something you have to do regularly,” he added. “It’s like the mob. You’re in or you’re out. There’s no half way.”

When he got out of prison in 2010, he knew what he was called to do. He began working at Oak Park Township with the title Community Youth Advocate. The township website states that its Youth Services “supports programs and services that work for the prevention of juvenile delinquency and which address youth who are at risk of becoming involved or are already engaged in inappropriate and/or illegal activities.”

He does part of the work he calls motivational mentoring right at OPRF during the 4th, 5th and 6th periods on Fridays. “What I do,” he said, “is create a safe space for young people to come and share and then I resource them. The youth who attend have to buy into The 9 Agreements:

1. Treat everyone with dignity.

2. Offer support to those who need it most.

3. Use language that doesn’t offend others.

4. Understand the liberation of learning

5. Listen to and honor multiple perspectives

6. Participate positively in mentorship

7. Honor the space.

8. Honor the agreements of confidentiality.

9. Speak words to empower.

Jackson said, “Values are important. You have to have shared values in order to get things done.” His business card declares, “Building CommUnity, And It Starts With YOU!” 

He described a typical Friday afternoon session. “When the youth–who are coed and 95 percent African American, come in we sit in a circle, feed them, recite The 9 Agreements in a call and response fashion and then go around the circle having each person say their name and if they agree with The 9 Agreements. If they don’t, they have to leave.” Jackson then gives them a prompt, like, if we’re talking about education, “on a scale of 1 to 10 how educated do you think you are?”

He does the planning for the Friday get togethers with students on Wednesday. The youth come into the Youth Activities Center. “We sit around and figure out topics we could discuss on Friday and pick one by voting,” he said. “We then hash out how we’re going to run the session.”

He also facilitates an early Friday morning session at the Oak Park Township building which he calls the Sunrise Circle. Run similarly to the sessions in the high school, adults arrive at 6:30 a.m., sit in a circle and are asked to accept The 9 Agreements. Then someone states a prompt like “who was a mentor for you” and each person in the circle takes a turn responding while the others listen.

Stephen Jackson has a vision that goes beyond OPRF and Oak Park. He has his own business called Global Community Associates and does consulting work with four school districts, National Lewis University and the Golden Apple foundation.

One of his dreams is to build a community center in Oak Park where “everyone from every socio-economic class can come and get what they need, like Austin’s Circle Urban Ministries in which he was active while growing up, where there is gymnastics and child care and a medical center and a law center.”

“Information in Oak Park is hidden,” he said. “If you don’t have connections, you won’t have access to certain information. If you don’t know certain people you’re ignorant to what’s going on. If you don’t have the financial resources, there are a lot of things you can’t join in this community.”

He is presently working on a memoir which he hopes will be published in January. “My life is a cautionary tale for all students, because I was trying to be something that I wasn’t,” he said. “If you keep on flirting with it, it will become a reality for you.”

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Tom Holmes

Tom's been writing about religion – broadly defined – for years in the Journal. Tom's experience as a retired minister and his curiosity about matters of faith will make for an always insightful exploration...

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