Confessions of a Headmaster

Who is Paul Cummins? He is an educator, clearly, since “Headmaster” is plainly the title he identifies with. He is also a father who does not want to leave his daughters with questions about who dad was or what he did, and he states from the outset that this is his main reason for putting together an autobiography. This is a motive that I can understand and support, since I, too, did not realize how little I knew about my own father, until the day I sat down to write his obituary and realized what an intelligent, capable man he was. At that point, it’s too late to do more than regret.

I had no idea, as I began reading this book, that I had ever heard of Paul Cummins before. At best, I hoped that this book would overcome the ugly mustard cover and slightly skeezy title and provide a good caring-educator story along the lines of Stand By Me. Instead, I discovered, as I read about the beginnings of Crossroads Academy, that I had indeed heard of Mr. Cummins, or at least, I knew of his work, from my own research into educational theory and experimental schools. His ideals of a curriculum steeped in the arts and creative freedom, learning joyfully, while also learning deeply, are principles that I try to employ, on a much smaller scale, in my homeschool. So reading more into the life and works of this man became personally enriching in a way I had not anticipated.

Cummins begins his narrative, as any good writer should, right in the middle of the action—with his appointment as headmaster of the St. Augustine’s by-the-Sea Episcopal School. This was where he would begin to make his ideas come to life, and started the whole business of creating schools that would become his life’s work—beginning with Crossroads, built so that the kids thriving in the environment at St. Augustine’s would have a place to go for middle and high school. After covering the highs and lows of his time at Crossroads, he then goes back in time, to his privileged youth, education at Stanford and Harvard, and his first few years of teaching, to bring us back to where he was at the start of the book. This was probably my favorite part, because it’s such a joy to see and experience the discovery of learning. The letter to his father, explaining his choice to go into education was written with such a passion that, for someone else, it might have seemed he was declaring a call to study theology. But perhaps there is not much difference between the two, after all. The final section moves forward to the time since he left Crossroads and started creating partnerships with public schools, in order to bring the quality and joy of learning that his Crossroads students had enjoyed to as many children as possible.

So, to anyone with an interest in education, I would strongly encourage not judging this book by its cover (as many people learned not to judge Crossroads by its ugly warehouse appearance) and give it a try. Cummins writes about his ideals, how he developed them, how he used them, even sometimes how he failed them, and he does it all in a welcoming conversational tone that goes nowhere near the academese that many educators fall back on. And then maybe take a gander through the brief bibliography of life-changing works that he gives at the end, and see what they can do to your own life.