What to do about the book proposal chapter outline

It sucks, I know...

I hope this isn’t a plan for some extremely creepy building but alas, I don’t speak Dutch and am too tired to investigate. Archief van Engetrim, Collectie Vlaams Architectuurinstituut - Collectie Vlaamse Gemeenschap

Unless you’re already an established book author and can half-ass your proposal or have an extremely time-sensitive topic and have to get it on bookshelves stat, you have to figure out your book’s structure before you sell it. I understand why this is the case, but for a reporter, it’s a bit of a mindfuck. In many, if not most, cases, you have to write a very, very detailed outline of the longest thing you’ll ever write before you’ve done most of the reporting and research. Of course, it can, and likely will, change in the process of the actual writing, but the structure and plan for the book is pretty much half the proposal.

Before we submitted my proposal to publishers, I’d reworked the chapter outline several times, experimenting with splitting everything into two or three parts, dividing every chapter into an essay and oral history element, having interludes interspersed throughout (I say this so breezily now, but this iteration process happened over several *years*). It helps that I decided early on that at least part of the book must be chronological, considering that it is, after all, a history. I don’t envy those who don’t have that organizing principle as a form of extremely useful constraint.

The book must, must, must have a clear internal logic. The way I check whether I’ve been successful in creating that logical scaffolding, whether in my own longform pieces or in my work as a developmental editor, is that I ask myself whether I can clearly articulate why piece of writing X follows piece of writing Y, why content X belongs in the first part of the work and content Y belongs in the second or third or fourth part. And, crucially, I check whether all these Xs and Ys fit under the the overall thesis or guiding principle of the work, as well as that of the section. Otherwise — sayonara, darlings. It sounds simple and obvious, but from my experience, it’s way too often forgotten.