Writing a Book: Part One (Ambition)

So I’m writing a book. In some sense, this is nothing new. I’ve wanted to write a book since I was probably five and since then I must have started seriously writing drafts of half a dozen, before abandoning them. But this one feels different somehow. I really think I’m going to finish it.

I don’t want to say what it’s about publicly yet (hint: it has to do with politics), but it’s ambitious — perhaps ridiculously so; when I tell people at parties about it they look at me as if trying to determine whether I’ve gone mad. My goals for it are ambitious too: I want it to be popular (how hard is it to be a ‘national bestseller’?), I want it to be great writing (accurate, nuanced, and hard-to-put-down), and I want it to make a difference (get people organized, change government policy). Oh, come on. Now you’re giving me that look.

I suppose most authors want these things, but it doesn’t seem like they try particularly hard. And in a way that’s understandable: writing 300 coherent pages is hard enough — why add all these additional requirements? But I have high standards for books. (I’m almost always disappointed.) I figure the least I can do is try my best to live up to them myself.

Just as I’ve always wanted to write a book, I’ve always wondered how you write one. The problem is that the kind of people who would write books on how they write books are usually pretty dreadful writers and I can’t stand their poor writing, let alone their sense of superiority. (This is why I kept throwing On Writing Well against the wall.) But I’ve never written a book before, so I don’t feel superior, and I’m at least trying to be a great writer. So for people in the same boat, I thought I’d write about what it’s like.

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It started with an email. I’d written a blog post on management that had gotten some attention, including a link from the famed Jason Kottke. Apparently the New York literati all read Jason’s blog, because an editor at a publishing house followed the link and read my piece and thought it might make a decent book. He worked for the business book imprint of a major-name publisher and invited me to give him a call and discuss the idea further.

Normally when I come up with book ideas, I don’t tell more than a couple people about them. I’ve certainly never talked to anyone at a major-name publisher before. So getting this email was thrilling. I’d always imagined I’d have to pitch my book to publishers someday, but now publishers were coming to me, and asking for a book! It gave the whole thing a seriousness those other book projects lacked.

I told him I was heading to New York soon and he invited me to lunch at the Knickerbocker. It was the kind of place you imagine New York businesspeople meet for lunch: guys in suits, wood-paneled walls, I think I might have even spotted a cigar.

The editor was very excited and encouraging, but as we talked I grew increasingly discouraged. I began to remember how much I hate business books with a passion, how ridiculously dumb and faddish they are. For his part, the editor complained about how the rest of the world didn’t take business books seriously. They sold ten times better than normal books, he said, but the New York Times refuses to list any of them on their prestigious nonfiction bestseller list (there’s a special section just for business bestsellers that’s only published monthly and buried away).

Furthermore, the books are apparently sold in the most degrading ways — motivational talks at the Learning Annex were mentioned. I’d always imagined myself as more of a Charlie Rose guy. I wanted to write a bestseller, it was true, but mostly for the respect, not the money. For the people I hang out with, I suspect writing a bestselling business book would bring me only ridicule.

Afterward I met with a prominent book agent that my friend introduced me to — apparently one of the town’s top ten. She was brilliant and enthusiastic and full of energy. Spending an hour batting around ideas with her was lots of fun. Her shelves were lined with the famous books her authors had published and I began to dream about a future among those names.

But that was just the intro, for the details she handed me off to an associate, who explained the next step was to turn my idea into a rough outline. So I went back to where I was staying and tried to do just that. But I just couldn’t. I went for walks, I pounded my head against the desk, I tried moving words around on the screen, but I couldn’t seem to find a way to make the business book idea make sense. The fundamental problem was simple: who would take business advice from a teenager?

As I was working on it, another idea (we’ll call it the politics book) began nagging at the back of my head. I tried not to think of it, but it wouldn’t go away. The more I told it to bug off, the louder it nagged. Finally, I decided I would get the business book out of the way quickly and then do the politics one. But as my idea for the business book fell apart in my hands, the plan for the politics book grew clearer and clearer. I began talking about it, getting excited about it, even doing a whole outline for it. It seemed so perfect, so right. Finally, my girlfriend asked why I didn’t just do that book instead.

The associate agent was tepid (I guess politics books don’t sell as well), but intrigued enough to suggest I pursue it. He said the next step was to work on expanding my description of the introduction. And somehow I got it in my head that the best way to do this would be to just try and write it.

Which meant I needed to figure out how to write.

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July 27, 2009