Back to Work No Matter What: 10 Things I've Learned While Writing a Technical Book for O'Reilly

17 July, 2011

I'm rapidly approaching the midway point in writing my book. Writing a book is hard. I love to write and am excited about the topic. Some days I wake excited and can barely wait to get to work. I reach my target word count without feeling the effort. But other days it's a battle to even get started and every paragraph requires a conscious act of will to not stop and check twitter or go for a walk outside. And either way when the day is done the next one still starts from zero with 1500 words to write and none written.

Somewhere in the last month I hit a stride that has given me the beginnings of a sense confidence that I will be able to finish on time and with a text that I am proud of. I'm currently preparing for the digital Early Release of the book which should happen by the end of the month, which is a big landmark that I find both exciting and terrifying. I thought I'd mark the occasion by writing down a little bit of what I've learned about the process of writing.

I make no claim that these ten tips will apply to anyone else, but identifying them and trying to stick by them has helped me. And obviously my tips here are somewhat tied in with writing the kind of technical book that I'm working on and would be much less relevant for a novel or other more creative project.

  1. Write everyday. It gets easier and it makes the spreadsheet happy. (I've been using a spreadsheet to track my progress and project my completion date based on work done so far.)
  2. Everyday starts as pulling teeth and then goes downhill after 500 words or so. Each 500 words is easier than the last.
  3. Outlining is easier than writing, if you're stuck outline what comes next.
  4. Writing code is easier than outlining. if you don't know the structure, write the code.
  5. Making illustrations is easier than writing code. If you don't know what code to write make illustrations or screen caps from existing code.
  6. Don't start from a dead stop. read, edit, and refine the previous few paragraphs to get a running start.
  7. If you're writing sucky sentences, keep going, you can fix them later. Also they'll get better as you warm up.
  8. When in doubt make sentences shorter. they will be easier to write and read.
  9. Reading good writers makes me write better. This includes writers in radically different genres from my own (DFW) and similar ones (Shiffman).
  10. Give yourself regular positive feedback. I count words as I go to see how much I've accomplished.

A note of thanks: throughout this process I've found the Back to Work podcast with Merlin Mann and Dan Benjamin to be...I want to say "inspiring", but that's exactly the wrong word. What I've found useful about the show is how it knocks down the process of working towards your goals from the pedestal of inspiration to the ground level of actually working every day, going from having dreams of writing a book to being a guy who types in a text file five hours a day no matter what. I especially recommend Episode 21: Assistant to the Regional Monkey. and the recent Episode 23: Failure is ALWAYS an Option. The first of those does a great job talking about how every day you have to start from scratch, forgiving yourself when you miss a day and not getting too full of yourself when you have a solid week of productivity. The second one speaks eloquently of the dangers of taking on a big project (like writing a book) as a "side project". Dan and Merlin talked about the danger of not fully committing to a project like this. For my part I found these two topics to be closely related. I've found that a big part of being fully committed to the project is to forgive myself for failures — days I don't write at all, days I don't write as much as I want, sections of the book I don't write as well as I know I could. The commitment has to be a commitment to keep going despite these failures along the way.

And I'm sure I'll have plenty more of those failures in the second half of writing this book. But I will write it regardless.