In the winding road that my life has taken, I’ve held a variety of jobs. The old story about someone who worked for the same company for forty years and then retired with a watch died a long time ago, and the result is that all of us are career nomads, moving from one place to another—and even to a whole new industry—as the job market ebbs and flows.
I like to think that I’ve enjoyed most of the things I’ve done professionally, but none gave me a bigger battle than my years as a classroom teacher. They began at the tail end of the 20th century, in a public school building on the South side of Chicago in a neighborhood known as Oakland.
Over the Labor Day weekend in 1996, I and a few other brave souls began the work of converting a portion of a one-time elementary school on South Lake Park Avenue into a high school. It was a small school, that had designs on becoming a charter school in its own right some day. The name of the school was Future Commons High School Multiplex, and the principal of the school was Constance C. Montgomery, who we all knew as “Connie.”
I loved and respected Principal Montgomery, and she had a sunny disposition that never seemed to wear off. Although I was a new teacher in every sense of the word, she was never anything but kind and encouraging to me. Even so, I struggled mightily to adapt to life in the classroom. The first year of teaching is a challenge that I wouldn’t wish on my worst enemy, but with the support I received from her I just barely made it through. And then I went back for another year in the fall, followed by two more years after that.
Each year I tried new things in the classroom, and some of them worked but many of them did not. I embraced the experimental nature of the school, which sought to challenge the idea that big schools and their one-size-fits-all approach were the best way to educate children.
The school itself was located in an interesting spot, just off of South Lake Shore Drive in Chicago. The school was in the shadow of several large high-rise buildings known as the Lakefront Properties, which had stood vacant for over ten years by the time the school opened its doors. In my first few days on the job, I would look up and tell myself there were snipers just waiting for the right moment to open fire and kill us all.
This feeling of impending doom went away in time, but it wasn’t long before the buildings themselves came down. They were imploded in one fell swoop in late 1998, and it felt something like watching the Titanic hit the iceberg. They’ll clear all the rubble away, I told myself, and whatever is built in its place won’t have any use for an experimental public high school.
The school never received the charter school status that it wanted, and in some ways it was simply ahead of its time. There’s certainly no shortage of charter schools in Chicago at this point in the 21st century, but at the end of the 20th century it was a step the city wasn’t yet ready to take.
In any other type of environment, and with any other type of leadership, I would have failed miserably in the classroom. But as it was, I was able to hold it together just long enough to see the first incoming class graduate in the summer of 2000. In some sense, it felt like I went to high school for a second time myself, only this time as a teacher instead of as a student. It was an experience that I’ll remember fondly for as long as I live.
The picture above isn’t the best quality, but it reveals the way I’ll always think of Principal Montgomery. My wife and I were expecting our first child, and the staff and students of the school threw us a baby shower one day. It was very touching that they did this for me, and I enjoyed being the center of attention for something other than a classroom activity or a homework assignment.
Principal Montgomery is tying a set of ribbons around my head, and the joy on her face outshines any deficiencies of the camera itself. I was scared beyond all comprehension at the thought of becoming a parent, but the outpouring of support I received from her and the rest of the school made me think that maybe parenting wouldn’t be so bad, after all. And twenty-one years later, I can unequivocally state it’s the most meaningful thing I have done with my life.
I know that she is looking down upon me today—and at everyone else whose path ever crossed her own—with a glowing smile on her face. Thank you for sharing your light and your love, Ms. Montgomery. Your memory will serve as an inspiration for everyone who was fortunate enough to know you.
Blue Batting Helmet 