Hacking, painting, and book writing

How do you go about writing a book? The longest thing I’ve ever written professionally is a 5,000 word feature, and I felt quite dizzy by the end of that. My dissertation at university was 10,000 but it was mostly gibberish, so that’s hardly encouraging.

It’s not so much the crafting of a half decent sentence I’ve been worried about, rather it’s the knitting together of what at times seems like a set of jumbled thoughts and case histories into something that has some sense of coherence. Hell, maybe even something that someone somewhere might actually want to read.

The formal answer to this question is that you have to set up your outline, a set of headings with the key bullet points in it, and then you stick to that. And when I had to submit my book for approval, I had to put forward a pretty tight outline, even though I wanted to tear the whole thing up almost the second I’d submitted it.

The problem is, I’ve never really written an outline for anythign I’ve ever written. Somehow my mind just doesn’t quite work like that.

My best time-wasting option when confronted with not being able to write an outline is to start mind-mapping. But in this case, it just hasn’t worked.

I’ve always related to Paul Graham’s description of hacking compared to university-taught programming in his brilliant essay Hackers and Painters.

“I was taught in college that one ought to figure out a program completely on paper before even going near a computer. I found that I did not program this way. I found that I liked to program sitting in front of a computer, not a piece of paper. Worse still, instead of patiently writing out a complete program and assuring myself it was correct, I tended to just spew out code that was hopelessly broken, and gradually beat it into shape. Debugging, I was taught, was a kind of final pass where you caught typos and oversights. The way I worked, it seemed like programming consisted of debugging.

For a long time I felt bad about this, just as I once felt bad that I didn’t hold my pencil the way they taught me to in elementary school. If I had only looked over at the other makers, the painters or the architects, I would have realized that there was a name for what I was doing: sketching. As far as I can tell, the way they taught me to program in college was all wrong. You should figure out programs as you’re writing them, just as writers and painters and architects do.”

So for the last few months I’ve just been writing – getting down dozens of thousands of words, chunks of chapters, none of them finished. The equivalent of Graham ‘spewing out code that was hopelessly broken’.

Every chapter or bit of a chapter is a separate file – all sitting there in a folder (backed up thanks to the utterly wonderful Dropbox).

Now, however, it tim eot beat it into shape.

So, this morning, on a flight to Stockholm, I’ve just gone through the slightly painful process of reading everything (all printed out and separated by little index tabs) through, and starting to put it all into order – weeding out the duplication, shuffling things round a bit, finding that a couple of my ‘big ideas’ are hardly ideas at all when I read them back, and something that I just rattled off on a train journey into town (about the types of denial incumbents go through when facing disruption) has a bit more potential than I thought.

And now, finally, I have my outline – scrawled on a piece of A4 (I tried photographing it to put it up here but the results were just too fuzzy) and it kind of works. It’s also not a million miles from where I started (I say that just in case my editor is reading this!).

I also have a fair of writing still to do – but it’s now clear where it’s all going. A bit late, I know – but I’ve crossed some sort of Rubicon.

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