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Why I Told My Students About My Stint in Jail

By Matthew Dicks
Why I Told My Students About My Stint in Jail

Matthew Dicks is an internationally bestselling novelist whose books have been translated into more than 25 languages worldwide. He is also an award-winning storyteller, a speaking coach, a blogger, a wedding DJ, a minister, a life coach, and—intriguingly—a “Lord of Sealand.” Despite his eclectic interests and rising fame, Matt continues to make the elementary classroom his mainstage as he pursues his 21-year commitment to teaching. He has shared his storytelling talents and insights with students from Yale University to Graded School in Sao Paulo, Brazil and many places in between.
One of my colleagues charges into my classroom after school and asks me why I told my students that I spent time in jail.
“What were you thinking?” she asks. “They were all talking about it at recess.”
My answer to this question is both simple and complicated.
The simple answer is this:
Four years ago, after telling my class that I had spent time in jail, one of my students approached me at the end of the day to tell me that his father was in jail. “I didn’t think I could tell anyone,” he said. “Can I talk to you about it?”
Last year, after telling my students that I was homeless for a period of my life, a student sent me an email explaining that she and her mom had been living in their car over summer vacation, and she was afraid that she might need to move back into the car someday, maybe when it was cold.
I was able to mitigate that little girl’s concerns and help her family access some much needed services. Most important, the mother of that girl was willing to talk to me about her struggle after hearing about my own. Prior to that, she had told no one about her brief bout with homelessness.
Just this year, I told my students about the time I had accidentally left my two month old daughter home alone. After putting her to bed, I worked on a book for a while and then decided that I deserved a soda from the local convenience store. I was pulling into the 7-11 parking lot when I remembered that my infant daughter was home alone.
I had forgotten for a moment that she even existed.
Today she is ten years old. She has no recollection of that moment of terrible parenting, but I told my students that I would never forget it.
Later that day, a student told me that he gets nervous when he arrives home from school and his parents aren’t home yet. He’s also ten years old, so this isn’t a case of poor parenting. The student is only home alone for about 30 minutes, and only occasionally. But I was able to speak to his parents about their son’s fear (which he was afraid to tell them), and action has been taken to put this boy’s mind at ease.
Why do I tell stories like this to my students? The simple answer is that stories open doors to the hearts and minds of your audience. They create an instantaneous connection with the listener. They establish common ground upon which the storyteller and listener can stand.
In a theater, this is a powerful thing.
In a classroom, this can be life altering.
But the question “Why do you tell stories about your life to your students?” seems ridiculous to me. Of course I tell stories to my students. I spend more time with them over the course of a day than they spend with their parents. Why wouldn’t I allow my students to get to know me?
Yet I know many teachers who choose to remain like a black box to their students. They create an insurmountable wall between their home and school life. They believe that this is the way of the professional. As a teacher, it is their job to impart knowledge, teach skills, and bestow wisdom upon their students in their assigned curricular areas. Stories about your personal life have no bearing and no place within the classroom.
I remember these teachers from growing up. Or I should say that I barely remember them. They were utterly forgettable human beings who attempted to impart knowledge and teach skills while remaining a complete mystery to their students. These teachers were, for the most part, uninspiring and ineffective. I did not work hard for these educators, nor did I behave especially well in their classes.
Why would I? They gave me no reason to believe in them. No reason to trust them or even like them.
Then there were the teachers who shared their lives with their students. Told stories about their childhood and their children. Shared their successes and failures. These were teachers like Lester Maroney and Patrick Sullivan. Jacqueline Leblanc and Mrs. Shultz. Teachers who made me want to become a teacher. Teachers who shaped my life and inspired me to learn, not through their cleverly designed lessons or brilliant orations, but through the power of storytelling. Their willingness to be vulnerable with their students. Their honesty and authenticity. These were teachers who found a way into my mind and heart by sharing their own.
“Okay,” my colleague says. “But why tell them that you were arrested? Why tell them that you were in jail? And that you cheated in your high school science fair? And bullied that boy in gym class? And lost your swim suit after diving into the pool at that girl’s birthday party? Don’t you want to be a role model?”
That is a little more complicated, but it comes down to this:
If we want our students to know us and trust us, we must be willing to be vulnerable. We must do the hard thing. No one is impressed or inspired by a bragger. The last thing my students want to hear is how good and right I was when I was their age.
This will do nothing to bridge the distance between us. In fact, it will only serve to widen the gap.
We cannot represent the ideal role model to our students, because presenting ourselves as the models of perfection will not cause students to want to share their hard truths with us. Role models are not the Platonic ideals of humanity. They are flawed, failed human beings who have managed to overcome adversity, apologize for their mistakes, pick themselves off the ground, move forward, and sometimes continue to make bad choices.
People—and especially children—must be able to see themselves in their role models, and this cannot happen if the stories that a teacher tells are pristine and perfect.
I share my foibles and failures. I talk about my terrible decisions and shameful acts. When I do this, my students are able to see themselves in me. They understand that success does not spring forth from moral certainty and consistent correctness but from the messiness of humanity.
When I tell my students about the boy I bullied or the time I cheated or that terrible moment in a swimming pool when I found myself naked among my classmates, I bridge that gap between me and my students.
We laugh together, and sometimes we cry together. I can’t imagine a better way to convince children that I love them.

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03/03/2020 - Ran
Great article and inspiration.
02/20/2020 - Belle
I fully agree with what Matthew revealed here. I am a teacher myself and I do not mind talking about my past experiences with my students. By telling them about some of my past mistakes and cocky shenanigans, students became more open and responsive to class discussions. I am not afraid to show my vulnerabilities to my students, as Matthew would describe his regaling stories. In all my 20 years of teaching, I have seen how students become positively see me as a teacher they can trust other than learning life lessons as well.



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