Talks with Teachers #3: Imprisoned Education

Within minutes of meeting Chaska Conrow, I learned three things about her job:

1.) Jail is different than prison (think shorter-term versus longer-term).

2.) Retributive justice is different than restorative justice (think punishment versus rehabilitation).

3.) The orange jumpsuits don’t phase her one bit.

Until last year, Chaska taught at Five Keys, a San Francisco Unified charter school that operates inside San Francisco County jails. The flagship school, located in the San Francisco men’s jail in San Bruno, offers five-week courses that allow inmates to earn credits towards a high school diploma while awaiting trial or serving out short(ish) sentences. Over the past nine years, Five Keys has expanded to other San Francisco jails and post-release sites, including the San Francisco women’s jail, a maximum-security jail above the San Francisco Hall of Justice, and post-release sites operated in partnership with Bay Area community organizations.

Chaska is a veritable chameleon of an educator, who taught everything from basic skills to GED prep at a variety of Five Keys sites. When I listened to her rattle off her complicated teaching schedule, I wrote one word in my notebook: “Adaptable!” A petite brunette in her early thirties, she has large, bright eyes and a calm, confident demeanor. In her time off from teaching, she started a nonprofit called Cup of Change that helped build a library in Nepal. Although she left Five Keys last year to move to Spain, here’s what she had to say about the myths and realities of teaching behind bars.

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The Rumpus: Let’s start with the first day on the job. Tell me about it.

Chaska Conrow: You know, it’s so funny: the first day you go in, it’s super scary. You’ve seen all the movies and you’re terrified that you’re going into jail and you’re going to be in a group of twenty-seven men who all committed some crime that got them there… But it’s pretty amazing that, as a teacher—and I think any teacher would feel this way—as soon as you start the class and start teaching, all of a sudden you’re totally in teacher mode. You don’t see them for the orange that they’re wearing, you don’t care or think about what they did or why they’re there, you’re just all about teaching them what it is you’re supposed to teach them that day. Within five minutes you forget you’re in jail. And really, they react in the same way that any student does. Obviously there are certain personality issues and conflicts, but if someone has good classroom management skills in a normal classroom, they’d be fine in a jail classroom. It’s not that different, really.

Rumpus: Can you describe the jail itself?

Conrow: The jail at San Bruno is actually really different than what you would imagine a jail to be. It’s really state-of-the-art and modern. There are no bars, they [inmates] live in pods, they have a common area with tables, and most of the day they can be out in those areas. They have glass door cells… We have an education corridor there with about ten classrooms. You’ll see your basic high school classes—Algebra, Economics—and then we also have a large group of students who are doing independent study. Aside from the fact that everyone’s orange and there are deputies in the hallway, it kind of just looks like regular classrooms. You see what you would see in more or less a normal high school class in terms of curriculum and the teaching.

There are also two other jails that I’ve been working at for the past few years. Those are maximum security jails—jails for inmates who can’t be at San Bruno. I’ve been working with a group of transgender students there—they’re there for their safety as opposed to having done something. These jails have your typical long corridor with barred cells. The transgender students that I work with have what we call a “tank”—a big, giant cell with lots of bunk beds.

Rumpus: How did you wind up working in jail? Did you seek out this particular context?

Conrow: Totally by accident. I had no intention of ever working in jail. I started out as an elementary school teacher and really didn’t like it. So I ended up traveling and teaching English abroad for a couple of years, and then I got back and began working with at-risk populations—16 to 24-year-olds that were doing a vocational training program and also working towards their GED. And then it just so happened that one of the teachers I worked with left and got a job at Five Keys, and she was my contact there. When she first told me about it, I was like, “Yeah, right.”

Rumpus: As in, “Yeah right, I don’t want to do that”?

Conrow: Exactly: “Yeah, right, I don’t want to work in jail.” But then I was contacted by the director of the school and agreed to do an interview. And to be honest, it was higher pay than I had made, far more vacation time, good health benefits. So I figured, sure I’ll do it for a little while as I’m figuring out what else I want to do. And then I ended up really, really loving it and becoming really passionate about it. It’s probably been one of the best things for me as a person—not just as a teacher, though as a teacher as well. It has allowed me to see an entirely different world and look at society in such a different way—encountering people I never really thought about before, or if I did it wasn’t in a positive light. And realizing that—they’re just people. I guess just realizing how easily I could be in their place and they could be in mine. The different situations our lives have presented. It’s been a great experience.

Rumpus: Tell me a little about Five Keys. How did it start?

Conrow: Five Keys is a charter school started by the Sheriff’s Department of San Francisco. The reason it was started is that Michael Hennessey, who was sheriff [of San Francisco] for many years, is very much pro-programs in the jails—more of a restorative justice approach versus a retributive justice approach. One of the areas that he found was important to address was education. The vast majority of those who are incarcerated don’t have a high school diploma, often far less, which correlates with recidivism—going back to jail. So Five Keys stands for the five key areas for somebody not to go back to jail: Community, Family, Recovery, Education, and Employment. The charter school is the Education component of those keys.

As soon as somebody is enrolled in the school, we access their transcripts from whenever they were in high school before, compare what they earned to California requirements, see how many [credits] they’re deficient, and they work on the credits to complete their diploma from there. So some people are really close—maybe they dropped out of school for whatever reason in the twelfth grade—and there are some who never went to high school at all. There’s a huge range. It’s more common to have people with very, very few units and sometimes no units, than somebody where you say, “Oh, so it looks like you only have a few units to go.”

Rumpus: Do you feel like you have more freedom as a teacher right now than when you were working in a traditional school?

Conrow: Yes, definitely much more freedom to adjust things and change things, and find things that work for your particular student instead of being confined to a particular type of curriculum. But at the same time, I’m working with students whose reading level can range from a first grade level to a college level—very rarely college-level, but sometimes. The average student I have reads at a fourth grade level.

Rumpus: You mentioned that semesters are short and that people are constantly coming in and out of the classroom. With so much flux, do you get to form relationships with your students over a longer period of time?

Conrow: I do. Sometimes I’m not with them long enough to form a relationship and in those cases I’m just hoping I give them a positive experience with education on the day that I see them. At my current location, I have students that have been there the entire year. I have some that have come and gone—and then come back again.

Rumpus: Have you ever had an experience that stands out as really intense?

Conrow: The scariest thing that happens inside of the jails is when a fight breaks out. And it happens fairly frequently—more frequently than we’d like. I had one fight in my class. It scared the shit out of me. And it was nothing compared to other fights. It was just two people who got in a disagreement and started punching each other. In that situation, I screamed at them to stop and they actually did.

Rumpus: Wow. Way to go.

Conrow: Yeah, that doesn’t usually happen. There’s a red duress button in the class in case a fight does happen. So you push that button, and then it gets really, really scary because the deputies—like, ten of them—come charging into your classroom and take down whoever it is—people who are currently fighting, there’s mace, people getting thrown to the ground… The hardest part is that you’ve developed a relationship with these people. They’re your students. To you, they’re not criminals or bad guys. So it’s really hard to see a deputy shove someone to the ground… Emotionally, it’s the worst thing ever.

The situation in my class was just an argument—I don’t even know what it was about, but it’s usually gang-related. There are a lot of precautions to keep conflicting gang members in separate classes. It takes a lot of work. You have classes right next door to each other with different gangs in each class, so they have to move them into the classroom one at a time in the morning—it takes a lot of time. Movement takes forever.

Rumpus: Because you don’t want them passing each other.

Conrow: Exactly. You can’t have them passing each other. So there have been a few teachers who had various fights. But there has never been a teacher harmed in a classroom. And I have never, ever felt scared of one of my students, or felt like one of my students would harm me. Ever.

Rumpus: As a woman, you’ve never felt anything?

Conrow: I mean, you’re in a group with all men, so initially you might get the guys who are going to say something inappropriate, or look at you inappropriately. But first of all, you dress really conservatively. You also develop a demeanor that shows you’re not going to take it. You don’t even need to say much. Once you develop a relationship with the person on a level that is about you being a teacher, all of a sudden that entire dynamic changes. It’s amazing. You’ll have a guy who normally on the street would be cat-calling you, and it’s totally just a student-teacher relationship. I’ve never had an issue. Initially, I might have to tell someone that a comment is inappropriate, but usually they’re really responsive to that.

Outside of jail, there’s no deputy standing there watching, so I had one student who stole my wallet and went on a shopping spree with all my credit cards. I’ve had a couple students threaten me.

Rumpus: Have you ever been fearful that something might come of the threats?

Conrow: It’s awful when it happens, but I’ve learned not to take it personally. There are much more rewarding experiences and positive experiences than those negative experiences. But you have to be prepared that if you’re working with this population, that kind of stuff could happen. And it has.

Rumpus: Tell me about the positive experiences.

Conrow: You know, when I taught elementary school, I was working in a lower economic area with minority students and feeling really frustrated at how terrible a job I felt like I was doing as a teacher. I was seeing all the students that fall through the cracks and now I’m seeing where those students end up—and that they’re the same people, just in older form. And they’re not bad people. It’s poverty and abuse and violence, and all the stuff that plays into what happens to a person and to the choices that they—well, the choices they don’t have—and that prevent them from being successful, whatever success is in life. So I think it has been that realization.

Also, so many of these people have children themselves…it’s really nice to feel like you’re doing something for these people that has a huge influence on a younger generation. Because they all have kids. It’s really rare to meet someone who doesn’t. And it’s going to keep happening unless we do something about it. Even though it’s really frustrating, because most of the time they do come back [to jail]—it’s obviously so much bigger than “give them a class and a high school diploma”—but I’ve definitely felt like I’m making a bigger difference in the overall scheme of things. I think elementary school just wasn’t for me. The whole school bureaucracy—

Rumpus: But the bureaucracy of the jail system is huge.

Conrow: It is. It’s terrible.

Rumpus: But you don’t feel like it affects your work the same way?

Conrow: No, it does. There’s a huge disconnect between the jail system and the charter school and its programs. It’s better than most places, I have to say. In most places, school in jail doesn’t even exist. We’re just trying to make something positive happen within that system. It’s hard. It’s really hard. It’s not an easy thing to do.

Rumpus: How is it hard?

Conrow: The hardest thing about the actual job is how hopeless it can sometimes feel. I’m working with a population of people who are sometimes of a younger age, but sometimes they’re older and I think, “How much of a difference can I even make?”

Rumpus: How old are we talking?

Conrow: My oldest student right now—he’s actually one of my best students—is 60. The oldest student I ever had was 72. So ranging from 18 to 72. Any youth programs will typically stop around 24 or 25 because beyond that, statistically, vocational training and educational programs are not going to make enough of a difference to change their lives in a way that would make them a successful member of society—working, earning their own money, that sort of thing. I mean, the older you get, the harder it gets to make huge changes to your life.

So it can get depressing in the sense that it can feel like, “Is what I’m doing really making a difference?” Especially in jail, which is such a depressing place to be. To go into jail every day and know that my students are kind of at their worst. But at the same time, I kind of see them at their best… And also just the system—we know that the jail and prison system isn’t really working. We have a prison population that is growing crazy amounts instead of shrinking, so obviously we need to try something different. So trying to work within that system is a challenge.

Rumpus: How do you balance your personal life with the stresses of the job?

Conrow: Vacation. We get the same time off as a regular school teacher, but we get it throughout the school year. It’s crucial to take that time to leave the country, or go on vacation and really be on vacation.

Rumpus: Do you think it takes a particular kind of person to do your job?

Conrow: I think it takes somebody who really believes in education and what education can do for a person—really believes in a person’s potential and ability and desire to change. And if you don’t, you can’t do this job. It would just be awful. You’re not graduating a ton of students or having tons of success stories, like students with high test scores. But if you feel like education itself can help people beyond a certificate or test scores—just the power of education beyond the traditional sense—then you can be successful. Most of the teachers who work at Five Keys didn’t fit into a traditional education system, so this works better for them, because it goes into a deeper sense of what education can do for somebody instead of just passing on to the next grade.

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Rumpus original art by Jason Novak.