"Imagination is the capacity to think of things as if they could be otherwise." - Maxine Greene

My first year out of my Master’s program, I taught ninth and tenth grade English at one of Boston Public’s monstrous high schools (~1,000 kids). I came in bright-eyed and bushy-tailed, ready to work hard and change lives. I had read countless books, I had written countless papers, and I had rocked student teaching. Oh, yes. I was ready.

…Actually, no, I wasn’t. None of those books, none of those papers, and none of my student teaching experiences had prepared me for a constantly-changing roster that assigned 36 kids to a room with only 31 seats (“Don’t worry—they’ll never all be here,” another teacher said); 120-minute blocks; and an administration that was so hands-off that unless a student was puking or bleeding, I had to take care of it myself. If I assigned a detention, the student was serving it with me; if the student didn’t show up, I had the power to suspend. Within the first week, there was a huge fight involving ripped out earrings, broken glass, a metal stapler, blood, and a concussion in the room next door. Unfortunately, that was only the beginning of the violence that my students and I had to witness that year.

Here’s a journal entry that I wrote on October 24, 2005:

I have come to realize that teaching in this school is a lot like riding a terrifying roller coaster...in the dark.

When you walk in every morning, you have no idea whether it will be a good day or a bad day. You work hard to make it a good day. You plan like mad, you get to school at 6:00am to prepare, you try to be ready for anything. But then you go and screw it up. You make a few mistakes. Small, but crucial. The day begins to unravel. The kids feel it. You feel it. You try not to show it, but the tension in your voice is too obvious to hide. Your frustration builds. Their frustration builds. You lose what you've worked so hard for the past month and a half to gain: their attention, their respect, their effort. The class is lost. Gone. Unfortunately, you teach two-hour blocks...so you still have 100 minutes to go.

And by the time your day ends, you are so exhausted that you can barely throw the broken pieces of your brand new bathroom pass away without crumbling. You wonder if any other job exists where one can work so incredibly hard and feel so completely defeated if even one part of the plan goes wrong. No job can be this hard to do well. Surely no job under the sun.

Kathleen Cushman says, “Good teaching requires the courage to look honestly at what is and imagine what it could be.” When I was struggling through that first year in Boston Public—a time I commonly refer to as ‘the winter of my life’—I looked at how poorly the school was run, how unsafe my students felt, and how alone I felt, and I imagined a school that served the same population but did it well. So I started looking, and I found City on a Hill. Here was a school that took the kids who lived next door to the kids I taught in Boston Public and got them to college! (As a side note, I hate it when people say that charter schools ‘weed out’ the worst behaved or the most behind students; it simply isn’t true—I can tell you, they serve the exact same kids.)

Here’s a journal entry that I wrote on August 30, 2006, three days into my first faculty orientation week at City on a Hill:

I'm really excited about this school. I definitely work with a fantastic group of people. I feel supported in so many ways (which can't be further from how I felt a year ago at my old school).  The exact moment that I realized this: My planning partner (who is also the Principal—all of the administrators teach!) and I were looking over my classroom contract from last year (a five-page document) and were able to cross off 90% of the ‘classroom procedures’ I had made up for my room because they already have school-wide systems in place that cover them. Everyone is on board; I am no longer an island unto myself. Hoorah!!

For me, quite literally, City on a Hill was a dream come true.

Ms. Gentry with her senior advisory on their last day of classes - May 21, 2010

Christine Gentry is a Ph.D. candidate in
the English Education department at Teachers College, Columbia University and a
Curriculum Coach and Lead Instructor at Student
Press Initiative. She taught high school English in inner-city Boston for
five years, four of which were at City on a Hill. She studied English and
Sociology at Baylor University and received her Master's in English Education
from the Harvard Graduate School of Education. Her long-term plan is to teach
future urban English teachers at the college level while always teaching at
least one high school class.