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On Writing a Book, Pt 5: What Makes a Book Great, and How Much Insanity Does it Take to Try Writing One?

By Dave Stuart Jr.

Our goal here is to make something that people rave about, that becomes part of their lives. The buried insights found in those other great works were not put there on the first pass. Work is unlikely to be layered if it is written in a single stream of consciousness. No. Deep, complex work is built through a relentless, repetitive process of revisitation.
–Ryan Holiday, Perennial Seller*, p. 58

Great books give us more than information — they give us company, inhabiting our lives. Early on in my career, the great books for me were those written by the types of teachers who get movies made about them, with perhaps the most shaping book for me being Rafe Esquith's There Are No ShortcutsEven though I've long since given up the idea that the ideal teacher spends his or her entire waking life with students, Rafe is still with me, one dear advisor on the path to producing a continuously fruitful teaching career. He teaches me to motivate my students through high expectations, and to treat the standard curriculum as the starting place, not the finish line.

As I've aged, however, I've found that other books speak more to me — books that make the infinite complexity of teaching more manageable and accessible. Here, I first think of Mike Schmoker's Focus, or Graff and Birkenstein's They Say, I Say (I love the high school edition with Jim Burke's foreword). Both of these books take a job that's impossibly complicated and make a regular person like me feel as if I can actually do it. They point me toward the “moves that matter most” and give me permission to basically forsake the rest. Books like this embolden the reader while making him or her a little bit the wiser.

Of course, the book I'm writing aims at being that latter kind of book. It certainly won't tell the tale of an extraordinarily magical classroom where the students travel the world and put on unabridged Shakespeare during the after-hours. Rather, I hope it paints a way for those of us who want to create ordinarily magical classrooms during the hours we're willing to give this good, yet not ultimate, calling.

To write that kind of book is a daunting prospect, one that first of all terrifies me. I'm not old enough (33), mature enough (ask my children/students), or experienced enough (11 years) to write that kind of book. I'm perfectly comfortable blogging at this point, but trying to write a book that you'll wear out from re-reading and referencing is discomfort defined. Blogging is so low stakes compared to a book. A blog post enters the fray of the noisy world, and the writer just hopes and prays that it makes it through the filters of the right readers, that it's helpful to those whose eyes it reaches. But even if it's not the right post for someone, it's okay — after all, it only cost the reader a few minutes, and the reader can always go to that other tab, or can unsubscribe. But a book demands so much more: it demands money, and it demands time and sustained engagement.

Shooting for that feels just crazy. But with this book, that's what I'm shooting for — contributing something to you that has an effect like, “Okay, I can breathe again, I can do this, I see the way.” And so I really get it when Ryan Holiday writes that such a goal “is one that should make any rational person tremble a bit.”

But this post isn't a plea for encouragement — I do feel encouraged. I've spoken through this book's material dozens and dozens of times to different districts and schools and organizations around the country. I've started talking through the manuscript with colleagues, and soon I'll hear back from reviewers. And last week, I had the privilege of working through the material with some sharp, like-hearted teachers in the 211 district of Illinois. I feel absolutely jacked.

And all of that is to say that the work now is relentless, repetitive revision. Five or six days a week, getting back into the book for an hour or so, working in clarifications and consistencies, working out speed bumps and fog. If you ever have any questions about the book writing process, please let me know. Thanks for reading!

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