Your Long Thanksgiving Read: Be Many Things

Editor’s Note: Guest author Sean Healy, a Chicago high school administrator and volunteer teacher in Cook County Jail, shares his story, “Be Many Things.” It’s a long read that will remind you of the many possibilities inherent in human beings of all ages.

Be Many Things


The Cook County Jail’s maximum security division smells like the bathroom of a bar that’s been hastily cleaned: bleach faintly hiding human waste. The walls are beige-white with nicks in them; scuff marks tattoo them up and down. There are heavy metal doors with small windows at the top. When you approach the doors, the eye in the sky belches out a loud buzzer and releases the locks, letting you know you’re constantly being watched. It never takes more than 3 seconds for any door to release.

The first time I visited there, I was dressed in a suit. It was a warm spring Tuesday in April.

“Sean, welcome to prison,” kidded David, the prison’s education coordinator. “Ready for your tour?”

We arrived outside the rec room and stood peering through a long line of windows. David told me that it’s relatively safe in there but to still be aware. As he was speaking I noticed the 50 to 60 men wearing beige uniforms marked DOC tapping each other and staring over at David and me. I kept thinking, I should have worn jeans.

David led me inside and fifteen of the men came over and encircled us. They pummeled him with questions: “What’s going on with the Bible study class?” “Can I get moved off my pod—I’ve been waiting to hear back?” “Have you heard about my request?”

I kept my eyes on David. He responded quickly and with a smile. He didn’t answer any questions directly, and seemed well-versed in responses we use in school all the time: “Let me get back to you,” “Just wait,” “Let’s talk about this later.” It’s easier than saying no.

Then David took me to the pod where the men would be given the opportunity to take the literature class that I offered to teach. I learned that day that pods are the groupings prisoners live within. They are arranged by age and then further by behavior. David told me that I would be working with guys who were on the pod with the best behavior.

I asked David what was the proper terminology—prisoner or inmate?

“Well, actually it’s detainee,” he answered. “Technically, none of these men have been convicted of a crime. They’re here because they either couldn’t pay their bail, or they skipped their bail hearing.”

“So, you’re telling me that none of these guys has been found guilty for what they’re here for? They could just go home if they had money?” I asked.

“Yep.” David said with a nod.

“How long do most of them have to wait?”

“It can take anywhere between a couple of months to a couple of years.” David said.
That response still echoes in my mind today.


When Having Dinner With Family Is Impossible, It’s Still Possible to Be A Good Man


Five weeks later, a consistent dozen or so guys were coming to our third literature class. I loved every minute of it. Every time the students seemed to be blown away with what they were exposed to and speaking about. The insights and connections that were made energized my own curiosity. We sucked the life out of the stories we read and enriched our own lives in the process.

Juan had distinguished himself as a leader in the class. He’s a short Mexican man who has a large tattoo of a crown across his entire neck. His face is covered in smaller tattoos which are blurry and hard to read (I quickly realized that it’s extremely awkward trying to read face tattoos; it’s like having a couple drinks and trying to read text messages except these texts are on someone’s face). Juan regularly expressed sincere gratitude for our class and me coming to teach it. I always appreciated that, and it made my time even more worth it.

Every class starts with a team builder question designed to make all of us vulnerable and therefore build trust. I always share first. The question that day was, “If you could have dinner with anyone, alive or dead, who would it be?” When Juan shared he spoke, as he always did, about his family.

“I’d have dinner with my wife and two daughters—Angel and Alexa. But, I have to tell you Sean this is a hard one for me, because my daughters haven’t talked to me since I got locked up. You know everyone in my community just thinks I’m a piece of garbage. A father locked up. It’s like I’m a bad person. I don’t know, maybe this does make me a bad person. My daughters won’t even call their Dad.”

There was silence for several seconds in the room as most of the students looked down at their hands or examined their pens.It took me some time to find the words to respond.

“I think we can be more than one thing though, Juan.”

“What do you mean?”

“Well I’ve learned in my own life, mostly through working at a school, that we can be many things at the same time. Many of my students just think they can only be one thing: I’m the smart kid, I’m a class clown, I’m a gang banger.  They find it hard to accept that they can fail a test and be smart. They can be a young man and cry. They can be a girl and an alpha. They can be confident and have insecurities. So, I don’t know everything about you, Juan, but I think you can be a detainee and be a good person too. You can be both things.”

After class was over, Juan stopped to tell me he had appreciated my comment. I told him that I definitely don’t have this “being many things” idea all figured out myself, but it’s something I try to remember, and I was glad it meant something to him. We shook hands and Juan walked toward the door, placed his hands up on the wall, and spread his legs as the guard patted him down before he exited the room.


Will My Students Have Time to Be Many Things?


Briston was in my office after he got in a fight in the hallway. He was sitting silently in the one of the chairs which faces my desk. He’s one of my freshmen advisees and often comes to my office when something’s wrong. Briston is tall with short hair in tight curls. His sweater is always dirty and is pilling in the middle. He’s one of the strongest leaders I’ve met over my years of teaching and most of that is due to his intelligence and confidence.

I was tired and disappointed—a poor combination heading into a difficult conversation with a student. “Dude, why…just why?” I said. “I’m not sure what to say to you. I’ve told you a million times how much potential I think you have. What you can be, what you are. But, if you keep it up you’re going to throw it all away.”


“Healy, what makes you think I can wait?” he said, as he played with a baseball on my desk. I knew he left off the “Mr.” on purpose and I chose to let it go.


“What do you mean?”


“You guys keep talking about college this and college that. What makes you think I can wait that long?” Briston replied.


“Well I never said it was easy, but it’s worth it. College helps you discover your passions. It unlocks doors of opportunity like no other experience can. I want that for you. I want that because of how it will affect all those in your life and the world around you. You know that.”


“Yeah, but what you don’t know is that I need things now. See these shoes? I bought them. My uniform? That’s from my pocket. How are you going to get me to drop what I’m doing to take care of myself and my mom for something that doesn’t pay off for years?”


“I…uhhh…I’m not saying it’s easy, Briston.”


“But, you don’t have an answer for me. What do I do right now? I have to keep doing what I need to. That’s how I get by. You don’t get it.”


He’s right; I don’t, I thought.


Briston continued, “Listen, this is the way I am. It’s the way I have to be. I heard you. I’ve listened, but I’m not going to change.”


I wasn’t sure what to say. How do you tell a kid what he needs in the moment isn’t a priority?


I tried my best to communicate to Briston what certain choices could yield—both positive and negative. He just kept rolling the baseball around in his hand.


Many of my students think that they can only be one thing: I’m the smart kid, I’m a class clown, I’m a gang banger. Their identities are so fragile, and at such an early stage of development that I think they often find it hard to believe they can be many things. They find it hard to accept they can fail a test and be smart. They can be a young man and cry. They can be confident and have insecurities.  


Briston is more than one thing every day. Outside of school, he’s an influential gang banger. Inside, he’s often a profound scholar. It’s a constant fight for him. I believe he wants to view himself as many things, as complex; intellectually I know he can understand that, but his worlds are constantly clashing and it’s easier for him to view himself as just one thing.


As an adult, I struggle to view myself as many things at the same time. To realize that what I view as my greatest weaknesses seen at a slightly different angle are my greatest strengths. For example, I constantly beat myself up for being so sensitive at school and often taking things personally. Although when I change my perspective I realize this is also what makes me so caring for others, it’s what allows me to be loving, and compassionate. It’s taken me years to see this and still it’s hard to stop in the moment and be kind to myself—to see that both things can exist: being sensitive is both a superpower and my kryptonite.


Then, I think of myself as a teenager. I only wanted to be someone who went to parties, the class clown, and that’s all I was in my head. It takes a lot of us a long time to know ourselves and our complexities.


Will Briston have the luxury of that kind of time? 


Three weeks after Briston’s fight, I saw him outside the cafeteria, standing across from our  English teacher, Ms. Tate.


“Mr. Healy, guess who got 9th Grade Student of the Week this week?” Ms. Tate said with a smile.


“Briston Thorton!” I said.


Briston hung his head with a smirk across his face.


Later that day– in afternoon advisory– I gave Briston a shout-out with all the boys. He jumped around, did a couple dance moves, and started freestyling his own praises before I told him to cut it out and come over to my desk with a smile.

Briston sat down and we went over his log of demerits for the week. Demerits at our school are behavior infractions which accumulate into detentions. Briston had one of the highest demerit counts in the entire ninth grade.


We scrolled past demerits from weeks prior:


1/17/17. 4D. Briston referred to me as a “bi***.


2/19/17 4D. Briston threw food at another student in the cafeteria.


3/8/17. 2D. Briston smacked another student playfully in the hallway.


“No demerits this week. Great work buddy.” I said.


“I know, I’m on it.” He replied.


We looked at his grades and noted that they were mostly Ds, and we came up with a plan. Briston committed to attending office hours to make up work he was missing from his suspensions. He left my desk, and I called up another advisee to check-in with.

Later that day I passed Briston’s picture on the 9th Grade Student of the Week Bulletin Board in the hallway. Under his name it said, “Briston has shown amazing behavior and character improvement recently and has worked every day to make himself and his classmates better. Briston is truly a scholar!”


It’s the truth: Briston is a scholar. He’s also a whole lot more. He can be many things. I just hope he remembers that too.

*The names in this essay have been changed to protect anonymity


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Sean Healy

Sean Healy is an Assistant Principal of a high school in South Chicago. Before becoming an administrator Sean was a Literature teacher for 5 years. Sean enjoys writing, reading, gardening, yoga, and improv. He lives in Wicker Park. You can read more of his work on his blog: