Chapter 92: Book Proposal Agony

I have never been a good book proposal writer. I have written six books and the long, maddening, courage-testing, confidence-shaking process of writing a book is far more appealing to me than the process of having to propose one.

Book proposals are pitching on anabolic steroids, far more extensive, demanding, and exacting than trying to convince an editor to commission you to write, say, 1000 or even 5000 words. Those you can, and really should pitch in a page; longer is not always the better.

But a book proposal? We’re talking 10,000 words, for starters. And that does not include a sample chapter publishers may want to determine whether you have the chops to pull off what you’re proposing.

Many writers complain about this. I know because a good many are friends who complain much the same way I do. Book proposals feel so out of whack with what we do. They are sales pitches aimed as much as to an editor as to a publishing house’s marketing department (“where does this fit on the book shelf?). Even as you are pitching, you don’t want, as one writer friend put it, to sound like you are pitching too aggressively. It can feel like learning a dance by following the footprints on the studio floor.

At its core, the problem confronting writers proposing a book is that they are, in effect, asking a publisher to front them enough money (the advance against royalties, which is often the only money a writer will ever see) to afford the time necessary to report and write a book that may, gasp, not necessarily succeed. Add to that the growing skittishness among publishers (Q:how do we know this book will sell? A: we don’t) and you, as a writer, are left to spend a lot of time learning enough about a subject and/or story to be able to convince a publisher that you are proposing a saleable book when, in truth, you may well have a ton of reporting still to do. 

It is one thing to pitch a book on, say, a year in the life of Vladimir Putin (“he’s promised me unfettered access…”) and quite another to propose a journey whose destination, stops and characters encountered along the way are still hazy. Writers of fiction have been writing journey stories since The Odyssey. But I have to believe that were Homer pitching his opus as nonfiction today he might encounter many publishers unsure whether readers really want to know about the Sirens and the Cyclops. 

I had never written a book proposal that my agent did not have me revise again, and again, and yes, again before he felt it was ready to take to market. Yes, market, which underscores what we’re talking about. I’ve written in an earlier chapter that I had hoped proposal writing was behind me when my old editor suggested that in approaching my new book, I think like a novelist, while faithful to the facts. 

What does that mean? I asked.

Don’t write a proposal, he replied. You are still unclear on what the book is about. Instead, write the whole book.

I was delighted at the prospect of being free to report and write and not have to deal with a proposal. I was sure my colleagues would think I was nuts. But they too had had to write proposals and were jealous at the prospect of being liberated from the process. 

I followed that advice and was having a lot of fun, so much so that I was looking forward to spending a break going down rabbit holes about the three partitions of Poland, beginning in the late 18th century. I thought the solution was to stop reporting and begin writing – the advice I got from my wife and brother. I wrote. I even opened a doc titled “ruminations,” which gives you an idea where I then found myself: in between. 

I assumed I could proceed this way until a friend suggested that I get in touch with his agent who, after listening to me ramble on about what my book was about, told me that I was going about this all wrong.

You need to stop what you are doing, he said. You need to write a proposal. 

Damn.

And damn if he wasn’t right.
Here is why.

As Samuel Johnson once said (and while we’re at it, what didn’t he say?) about the prospect of one’s hanging, a book proposal does sharpen the mind. This is especially so for people like me who are not linear thinkers. (A show of hands please for those whose thought patterns begin at Point A but then quickly veer to Point H?). Reporting ambitious stories is for many writers a process of putting yourself in a position where images, characters, quotes, scenes, and random facts come hurtling your way. It is all you can do to keep up with the rush of information, even as you open more and more folders to store it all away. 

I know many writers, both young and experienced, who find themselves overwhelmed, lost, and desperate to make sense of what they have. Even as they are by their nature inclined to forge ahead and learn even more, they – we – need to remind ourselves that we periodically need to pause, and assess, and even go back to the beginning and ask ourselves what we’re trying to learn.

This is not so easily done. The fun part, after all, is the reporting, the gathering, the thrill of discovery. There is always something new to learn. Many people know how to write. Far fewer know how to report. It’s what sets us and our work apart, and so slamming on the brakes feels like sapping the delight out of that work. 

But then comes a moment when a friend or colleague or perhaps even an editor asks what you’re working on. And as you begin telling them you notice they are looking away, or at their watches or phones because you’ve lost them. 

It is axiomatic that the longer it takes to distill the idea at the heart of your project the less you actually understand what it’s about.

I do not recall what I said to the agent that day but I suspect that things began to go south when I started using words like: also, seems, broadly speaking, and touches on the theme of this and that. I want to believe that my explanation did not devolve into “moreover” and “policy” but I cannot be sure. What I suspect he heard that day was a writer who had an idea that was maybe 80 percent formed. The missing 20 percent was where the work lay, and not only to convince the agent and perhaps an editor of the worthiness of my idea, but especially myself.

Go write a proposal, he told me, and when you’re ready, I’ll be here. 

Kind man.

I’ve been at work on my proposal since the summer, with time off for teaching and other projects. I’ve so far written about 12,000 words and I am not close to done. The hardest part was the introduction, 1500 words that took me weeks to write. Weeks. I am a fast writer but this was so very hard. I took long walks and talked to myself, asking out loud, “what do I want to know?” The answer did not quickly materialize and I despaired that I would ever find it.

It can take forever to distill a framing question and in the end it only really works if it is very short – no more than five words – and poses a question that is at once simple to state but complicated to answer.

I’ve mentioned this story before but now I feel confident that I have reduced the question to its essence: who was my friend? He died 37 years ago and yet he remains a part of my life. Why is his final resting place on the edge of a kibbutz in the Negev Desert? To answer that question I will need to go back in time to trace the stories of his family, and mine.

I can see the book now. I can see the arc, the characters, and the drama. I can see how to pace it, how to use chronology when necessary and veer from it when it undercuts the tension. I know where the book begins and where it ends. It has come alive for me in ways it had not when I was reporting and only beginning to write in random fashion.

I needed the work of a proposal – the unfun, step-by-step, crafting of a detailed pitch  to get me here. I recognize that even as I would so much rather be reporting and writing, I have learned enough to be able to convey to an agent, editor and publisher that I have command of the material.

No one should write a book they do not need to write. The money, protracted over time, is lousy, and the work itself can feel isolating and endless. But if you do have a story that you believe is worthy of upwards of 50,000 words, you must do it. 

Six months ago I might well have suggested you just write the book. But that, I now see, would have been an unwise suggestion.

I want very much to finish my proposal so I can return to working on my book. That will wait, but the book will be better for it.

I do not like writing proposals. But I must.