First things first: Hire Betsy.
Second things second: this is a summary of what working with Betsy Rapoport was like. I hired Betsy to help me with my book proposal. She was a former Executive Editor at Random House and had been behind more than a few tremendous books.
I of course, knew none of this until my agent told me. But it quickly became apparent that Betsy was revered in publishing circles. She would later tell me that she was also a “legend in my own mind,” so she was not wanting for confidence. I needed help. What I was learning was that when it came to writing the actual sample chapters for the book, I was having a very challenging time.
The perils of believing your own hype
I know I write pretty well. I better! I’ve spent about a decade doing it in various formats and for various purposes and there would be something seriously wrong if I hadn’t improved. So of course I write better than most people who don’t do it every day, or who hate to write.
But I honestly don’t slave and toil writing this blog. I write here for fun and because I have a good time with the readers. The stakes are low and there are standards I don’t hold myself to because of that. There’s some good stuff here, and there’s some sloppy crap.
I do like compliments. Who doesn’t? But too many of them can cloud judgment. I assumed–wrongfully, woefully, dreadfully, and naively–that because I created a fairly well-written and moderately-read blog, editors would be bowled over by anything I sent to them.
As it turns out, there’s well-written and there are book-level tiers of craftsmanship, which have proven to be a totally different sport for me.
“You haven’t thought this through enough,” said Betsy in one of our earliest conversations. That was true. Thinking it through any harder would have required effort.
That is a long-winded way of saying that I was willing to have help with the sample chapters and I had good reason to think that Betsy could provide it. Also, she told me that she was once so poor that she made cardboard shoes for herself, and that was incredibly endearing. And I liked her smile on her website.
How’s that for due diligence?
How we started
A long phone conversation in which we tried to figure out if we’d be well-suited to working together at all.
She asked lots of questions and let me ramble. She would interrupt me and then ask more questions. She used lots of Yiddish words I didn’t know. I could tell she was taking notes the entire time because she types very loudly and I could hear the deafening, rapid-fire clacks over the phone.
She asked, “What have you written so far?”
What I had written so far
I had spent six or seven months just vomiting up whatever I thought of. I was completely undisciplined beyond my one rule: write every day, do whatever it takes to keep your fingers moving. Clean the mess up later.
What this meant was that when I’d get stuck telling a story, or trying to recreate a memory, and it started to feel boring/difficult/worthless, I’d have to start writing something else.
These pages were not organized into chapters, or really even themes. They were just a giant mess that we might generously a call a rough draft of a really rough draft of something terrible.
“Send me all of it!” she said.
“Really? It’s about 180 pages.”
“Yes, I want to see it all! I can’t wait! I’ll know what we can use from it. In the meantime, build a timeline of what you think the story is.”
“Also, you have to disagree with me if you think I’m wrong,” she said.”I’m good at this and I’ve done it for a long time but I’m not infallible.”
This ran to about 30 pages. I basically laid out the major events of my life up to the present, then tried to divide them all up into a rough chapter outline.
I had several themes I wanted to incorporate into every chapter. I jotted down suggestions as to which stories might best be applied to serve the themes in chronological order.
This was not fun, but proved very useful to us.
Actually writing and editing
Betsy returned segments on that 180 page mess I sent to her, with a surprising amount of it proving to be salvageable. “Sometimes you might write 10 crappy pages to find one exquisite paragraph.”
When I would start a chapter, Betsy would essentially say “Okay, tell me this part of the story.”
“Just go do it.”
“It will be crap.”
And so off I would go. Over the first five chapters, I would generally submit between 40-50 pages to her at a time. 40-50 pages/chapter. It was grotesquely overwritten and fumbling, but I would get to a point where I had no idea what else to do with them. But she always knew. These chapters each got whittled down by between 10-20 pages.
She would return the documents to me with suggestions, excisions, and notes about changes she had made. Sometimes entire pages would vanish. Sometimes paragraphs at the end of the chapter would be at the beginning of the chapter.
She would clean up my grammar, improve sentence constructions, get rid of the passive voice.
More often she would say things like “Expand this part” or “This will go in a later chapter” or “How would you feel about going in a different direction with this part?” or “STOP FORESHADOWING!” By the point she started typing in all caps we were pretty good pals, so I didn’t mind.
If fact, as I learned about what annoyed her, I started misspelling things on purpose, trying to see how carefully she was reading. She usually caught them.
She believed for a long time that I truly didn’t know how to spell “involuntary.”
Now that I look back on it, I think one of the most valuable lessons was to learn to try and anticipate the questions that the writing was raising. What I mean by that is that if I hinted at something or left the language vague or open to misinterpretation, I would get feedback like:
“The questions are slowing me down. Don’t make me guess.” So I learned to look at my own writing paragraph by paragraph and try to see if it prompted questions that created confusion, or that “slowed me down.”
But I’m not an editor. This issue of slowdown never would have occurred to me. But once I saw it, I couldn’t unsee it and I was increasingly aware of when I was doing it.
Editors do not read like normal readers when they’re on the job. They are there to figure out what serves the narrative. To create a compelling product that will scream to be purchased. That will be truthful and hopefully have commercial appeal.
We really didn’t have any, so we proceeded more leisurely than I might have with another editor. The reason was that I had a couple of speaking engagements coming up within the year and we wanted to wait to submit the proposal until I could put those speaking credits in it.
So it was pretty breezy. Not easy–we did a lot of work, but it was almost always enjoyable for me. The 1% that wasn’t wonderful had to do with really delving into parts of myself that I don’t like to spend time with. To tell the right story I had to think about things I prefer not to. But that had nothing to do with her, I just blame her because she was the one dragging it out of me.
I think the process would have been similar if there had been more of a time crunch. Editors edit as a job. I have no doubt that she could have worked as well or as insightfully in a pinch. But I’m glad we didn’t have to find out.
The finished product
When I look at what we did–at what I wrote–I can’t believe that I had a hand in it. If she were here Betsy would slap the back of my head and say “You had the only hand in it!” and “I’m just one of the little people.” But it was really a joint project. Yes, I wrote the vast, vast majority of the words.
But there is some really beautiful writing in there and she got that out of me. It works. It feels like a book, not a looooooong blog post, which is sort of what my earlier going-solo attempts resembled.
Now I’m starting the process again with a new editor who will take me through the rest of the book. Once I have this next round behind me, I’ll let you know how that all went.
Questions? Have at it.
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