How to Write a Book Proposal, Ranked

I spent some time recently rewriting a book proposal for a narrative nonfiction book. Some parts were easy. Some parts were hard. Here are my thoughts on the easiest parts and the hardest parts, ranked.

Image via HuffPo

Image via HuffPo

The Overview. This is the part of the proposal where you deliver the elevator pitch of what the book is. IMO, you can do this in one of two ways--although, of course, you could also think of yourself as blending the two. Either you can talk directly to the reader--which I think is a more masculine approach--or you can perform the act of being a writer on a stage--which I think is a more feminine approach. I actually did each one for two different-but-related iterations of this proposal. I ended up going with the former. Frankly, I think the former states its value and the latter asks the reader to state its value. In negotiating, the former is referred to as "anchoring." I found the more masculine way of doing it to be easier, but that's just me. Difficulty level: Medium. Rank: 7.

The About the Author. This is my favorite part of the proposal to do and for me the easiest. I think it's easy if you have a platform, but I suppose if you don't, it would suck. After I do this part--which I've done as anywhere from one to three pages; this time it was two pages--I tend to feel more positive about myself, like, look at all I've done! I guess if you don't have much of a platform, you could feel like you were trying to knit a sweater out of dental floss. Sucks for you. Difficulty level: Easy. Rank: 1.

The Marketing Plan. Man, are there a ton of ways to do this one. At one point, like, a year ago, I paid a young freelance editor to talk me about a different proposal for an hour, and she sent me another proposal that had sold. That author knew what was up; he'd worked in the industry. He had bullet points, and it was a plan. It wasn't some writer nattering on about things they may or may not do or may or may or not know how to do. I've worked in PR and gotten paid to make stuff go viral online, so I know how to do this stuff, and I ended up going with something pretty basic. I think, based on a lot of what I read, you want to make it clear that you get this is a hustle, and that you're a writer who can hustle, so I tried to convey that. Difficulty level: Medium-easy. Rank: 3.

The Comparative Analysis. This proposal has the best comps section I've written for any proposal. It has five books on it, and I read every one of them closely, and I thought about how mine was similar and how mine was different. In a way, my book doesn't have a lot of comps, but I think my analysis did a good job of positioning it in the market. Having access to that database that tells you what the real book sales numbers are would've been nice. Difficulty level: Medium. Rank: 4.

The Timeline. I wasn't planning on doing a timeline for this book, but along the way I saw another proposal that had sold, and that person had included a family tree, and I think that got me the idea of a timeline. Did you know there's a timeline-maker thing in word? True story. I LOVED DOING THE TIMELINE. It was SO MUCH FUN. I think I originally thought it would have like 15 things on it, but it ended up having 30. I loved that it looked really professionally laid out, and that it enabled me to combine visuals and text, and that it looks like art. If you get stuck on your proposal, make a timeline. It will make you see things clearer. Difficulty level: Medium. Rank: 2.

The Outline. I wrote another book proposal last year for a different book, and the outline for it was so easy. This time around, the outline was very challenging. It ended up being quite long, and it required me to interweave multiple stories. It was intellectually, emotionally, and structurally challenging. I think it asked me to go against how I operate, which is intuitively, and pushed me to think in a linear fashion, which I don't. I did not enjoy this experience. But I think it came out strong. There's so much interesting stuff in it. And some great writing. My hope is that it serves as an invaluable road map as I move forward. Difficulty level: Nigh impossible. Rank: 8.

The Sample Chapter. Compared to the outline, this is easy-breezy. Finally, you get to do what you do best: write! This is scenes and dialogues and humor and sly winks and action. In fact, I'd argue it's everything that a book proposal isn't. In a way, it's child's play. And that's nice. Difficulty level: Medium. Rank: 6.

Oh, and ... There's the title, the title page, and the epigraph. These things changed over time, but in the end I decided to go with the most high-impact choice that was the most simple. Difficulty level: Not bad. Rank: 5.

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When the Writer Wanders

In the last few years, I've undertaken some trips that revolve around writing. An investigative journalism conference in New Orleans. A storytelling conference at Yale. A month-long writing residency at the Carey Institute for Global Good. And another residency on Martha's Vineyard. There were pluses and minuses for all of them, but here are a few reflective thoughts.

Just go. I spent a fair amount of time trying to talk myself out of all these adventures. Because that's what they are: adventures. Here's what writers do too much of: think, talk themselves out of things, and sit at a desk. Whenever you're doing pretty much anything that isn't what you usually do but is in service of you, you're doing the right thing. You will concern yourself with real concerns: money, time, guilt, etc. But there are ways to manage all of these things. Once you start executing your plan, and, better yet, once you find yourself there, you will sense on some level, hopefully, that you're doing the right thing. Why it's the right thing may not be clear right away.

You take the bad. There were things I deeply didn't like at some point during these adventures. The investigative journalism conference was: not freelancer-friendly, overpopulated by FOIA nerds bragging about their data-driven discoveries, attended by a certain number of on-air news personalities including women wearing sleeveless dresses in primary colors. I felt like a dateless dipshit at the prom for much of the time. But it meant I got to spend several days doing nothing but thinking of myself as an investigative journalist. I learned a lot: about how to do those FOIAs, about how to win a Pulitzer, about how to be who I am.

You take the good. My favorite experience was the residency at the Carey Institute. It was in this amazing rural area in upstate New York, and the trees were aflame with autumn. We were the first group in the program, and it had this air of bristling excitement. I was woefully underproductive on the page--or so it seemed at the time. But that was the start of the journey that's taken me to the place I am today. And that? It feels like a good place to be.

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My Twitter Protest

Ever since The Man I Didn't Vote For was elected, I've been protesting in the same way that most white people do: posting stuff on social media so I feel like I'm doing something but in fact I'm doing nothing. I combine famous quotes with pictures of president-elect Donald Trump. Here are a few for you to enjoy or dislike.

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Order the perfect holiday gift today!  Buy THE TUMOR, a "masterpiece of short fiction" by Susannah Breslin.

Working for a Living

As usual, I'm for hire.

Here are a few things I can help you do:

1. Develop your reality TV show ideas (I've worked on true crime, adventure, and miniseries)

2. Blog (TIME.com named me one of the best bloggers of the year in '08)

3. Write (I'm a journalist with bylines ranging from Harper's Bazaar to Salon to Variety)

4. Advertising (I've worked with Publicis Groupe and Weber Shandwick)

5. Consult (I've helped cast feature films and TV shows)

My LinkedIn is here. You can email me here.

Order the perfect holiday gift today!  Buy THE TUMOR, a "masterpiece of short fiction" by Susannah Breslin.