No. 51 | Seven things I learned while writing my first book

I wrote a book, and it comes out on October 16. It’s called Writing for Designers. It’s the longest thing I’ve written since the “lady Die Hard” script for my college screenwriting class about a female Vice President (I imagined Sigourney Weaver) kicking ass after terrorists took over the grand opening of the world’s tallest skyscraper.

I learned a lot while writing the book, and honestly it feels like I’m just barely starting to unpack the lessons from this project. But here’s a starter list of seven things I learned while writing my first book.

1) That that Mark Twain quote about short letters is true as hell.

The more of a hurry I was in, the less I was able to think critically about what I was saying, in what order, and why. As deadlines came and went (and got scooched back after begging forgiveness), the length of my manuscript expanded exponentially. The first full draft of the book was way too long, mostly from cruft I could have shaken off on my own if I’d been more on top of things. Some cruft is inevitable, of course, but not, like, 60 pages of it.

2) That the book isn’t me.

I unwittingly tried to jam a lot of stuff into the book that was personally interesting to me but ultimately only tangentially related to the main topic. My editor helped me see that while that stuff might be interesting to other people like me, it didn’t want to be in this book. I had to learn to do a lot of letting go and get comfortable with the book finding its own shape. It was disappointing at first, but the book is much better for it.

3) That heartache breeds procrastination.

In between pitching the book and signing the contract to write it, I got dumped, hard, from the most serious relationship I’d been in since my marriage. This was not great timing.

I tried to throw myself into the work, but I was just not in the right mindset. All I wanted to do was eat ice cream, go to loud concerts, binge familiar shows on Netflix, and whatever else heartbroken people do. To my credit, I did start working on the book right away, but because concentration was difficult, I became overconfident in my early progress. “Hey that was a solid 10 minutes of writing, let’s reward ourselves by watching an entire season of It’s Always Sunny.” Suddenly a week goes by here, ten days there, without so much as thinking about the book. No good!

4) The difference between restless and tired.

The book was only getting made when my was ass was in a chair and my hands were on a keyboard.

I learned that sometimes when it felt like I just couldn’t write any more, the actual problem was that I just couldn’t sit in that particular chair any more; I needed a change of scenery. I wasn’t always done writing, just restless. Some of my best writing days were spread over three or more locations: buy a coffee, write for an hour, pack up, bike somewhere else, buy another coffee, write for an hour, pack up, bike somewhere else, buy another coffee, oh no I’ve had too much coffee, drink a bunch of water and try to come down from caffeine overload, write for an hour, and so on. (I also eventually learned to order decaf.)

In particular, I got a ton of work done at Open Book in downtown Minneapolis and Five Watt Coffee in Northeast Minneapolis.

5) That, taken literally, “write drunk” is bad advice.

I don’t know about you, but alcohol immediately makes me stop being productive. If I’m lucky I’ll get some laundry folded or unload the dishwasher after a glass of wine, but I’m sure as hell not going to pull out my laptop and do 90 minutes of thoughtful work on a big project. Tomorrow Scott can do that! Tonight Scott wants to have another and play guitar.

6) To make lots and lots of outlines.

I had to make an outline to pitch the book, but that was only the beginning. I found myself editing and re-editing that outline, expanding and updating it as I went along, and making lots of other quick outlines on paper, even just for a sentence or paragraph. A book is too much to hold in your head. I had to constantly externalize things onto paper in order to stay on track. If the draft was open on my computer, you can bet there was also a pen and paper on the table.

7) That I can do it, damn it.

I didn’t tell very many people that I was working on the book because I wasn’t sure I could really do it. I thought it was very likely that I would fail or give up and I didn’t want to have to explain to people why it wasn’t coming out. This wasn’t a brave choice, but it’s the choice I had to make to get it done. And I did get it done!

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Originally published as List No. 51 of the 7x77 newsletter project.
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