My First Time: Katherine A. Sherbrooke

My First Time is a regular feature in which writers talk about virgin experiences in their writing and publishing careers, ranging from their first rejection to the moment of holding their first published book in their hands. Today’s guest is Katherine A. Sherbrooke, author of the new novel Fill the Sky, and a memoir, Finding Home. Katherine is a graduate of Dartmouth College and Stanford University, is an entrepreneur and writer. She currently serves as Chair of the Board of Grub Street. She lives near Boston, Massachusetts with her husband, their two sons, and a black lab.

The First Time My Book Was Done

I have always been a big believer in revision, so by the time my first manuscript was done, it had been through countless iterations. I had work-shopped almost every chapter, revisited tricky scenes with my writing group, and incorporated feedback on the entire manuscript from three trusted readers. The changes along the way ran the gamut, from adding additional points of view, to removing whole pages of exposition, pretty paintings that were hard to destroy but had no impact on the characters in the room. Then I spent several months honing and polishing. And finally, I was done.

That is, until I started over.

At the time, two writing friends of mine were enrolled in Grub Street’s Novel Incubator, a year of intensive manuscript revision under the tutelage of novelist Michelle Hoover. We had all started our novels at the same time—theirs were both excellent— and I was amazed when they described how much their books were changing in the class. The work they were doing wasn’t just moving furniture around that wasn’t working quite right, but whole-scale renovations. Some inner contractor told me that one more look at my manuscript might not be a bad idea. Michelle Hoover agreed to give it a read.

Michelle explained her timeline and process, which would include a written review of my book followed by an in-person discussion. Anxious to start submitting my book to agents without too much further delay, I suggested we schedule our meeting in advance, perhaps a day or two after her report was due. She hesitated, suggesting I should take time to process her comments before we spoke, and that I might not know how much time I would need until I read her report. I tried to explain that I was a fast processor of information and was practiced at quickly integrating feedback—I knew I would want to dive in right away—but she insisted we wait, and so I complied.

The day before her report was due, I went out to dinner with a group of close friends. We had all worked together at the business I had co-founded many years before, and it had been a while since we had all caught up. I excitedly told them I had finally finished my novel, that I was waiting “as we speak” for feedback from a teacher and novelist I really admired, but was hoping to have it out into the world soon. Even as I said things like, “she’s really tough, so who knows, she might tell me it’s terrible,” I secretly anticipated her rave reviews. I envisioned her amazement at how little there was to change, even without having enrolled in her intensive program. Everyone at the dinner table told me they couldn’t wait to see my book on the shelves. I would soon be on my way as “novelist,” a life-long dream.

As I boarded the commuter ferry that night, my email dinged. Michelle’s report was ready. What a perfect way to end the night—her words representing the last steps in the bridge between my old world of business and my new one as novelist. As I opened the file, several things struck me right away. The first was that her report was twelve pages long. Next, that it was single-spaced. Even a prolific writer doesn’t need five thousand ways to say “bravo!” The third thing I absorbed before my eyes began to blur was that it had only taken her two or three lines to tell me what she thought was working in the book before launching into the list of things that needed to be reworked. Furtively checking to see if there was anyone on the boat I recognized, I forced myself to read all twelve pages, twice. Then I cried the rest of the way home.

I didn’t request a meeting that next week. I was too busy being curled up in the fetal position on my couch. Nor did I request a meeting the week after that—too busy trying to uncurl myself. By the third week, I noticed that her comments had sprouted some new ideas about the book, tender and tiny, but taking root nonetheless. Two weeks after that, I had a host of tentatively drawn mental sketches for the kinds of changes I wanted to make, changes I knew the book had to have if it was going to be sound. Six weeks after receiving her feedback, I was finally ready to sit down with Michelle.

I outlined for her the things I was thinking about changing—switching the whole book from first person to third, collapsing four key characters into three, flying a back-story character to Ecuador so they could be in-scene, and adding a story-line I hadn’t previously considered, just to name a few. We talked through it all, and she validated the choices I had made. And then I asked her the most important question of my writing career thus far.

“Given everything I now want to change, if you were me, would you revise the manuscript I have, or would you start over?”

Michelle thought for a moment or two, and then looked me in the eye. “I would start over,” she said. It was a brave response, but I knew she was right. And I am grateful she had the courage to say it.

So I started with a blank screen, and began again from page one.

The truth is, starting over isn’t really starting over. I had developed a world that was real to me, I had created several characters that were living and breathing beings in that world. I just had to find a different way to tell their story. I approached it a bit like writing creative non-fiction. The “facts” were all there, but I needed to highlight different moments. The characters were already formed, but I had to illuminate their personal journeys in new ways. For me, it’s always the mental blueprint of the world and the birthing of the characters that’s the hardest. Putting them in scene is the fun part. So while it had taken me over two years to write the first version, I completed the new one in under six months.

More feedback ensued, my trusted readers weighed in again, and then, finally, one glorious day, I was really done. (Well, there was that revision for my agent, and then one more during the submission process…and then several more for my publisher…but who’s counting?)