An OODA Perspective on The One Week Book

by Aaron on December 22, 2011

Originally, the plan was to find organize core posts and auxiliary posts into chunks, those chunks into chapters, those chapters into sections, and those sections into a book. This was fine and dandy, but it basically failed to account for that it assumed that I would have any idea what would be turned into the book.


That is to say, it assumed that I would be able to find the core posts that describe an idea, without knowing what ideas I would want in the book. It assumed I knew what would work well in the book before I understood what the book was trying to be.


Shifting Gears

Luckily, I only tried to implement that plan for a few hours.


When I did my exploratory archive binge to find core posts, I started thinking about the sections and chapters that the book would include. I started mentally sorting the posts into categories, and discovering new categories. I was looking for the ideas while I was paring down candidates for posts to include in the book.


Interestingly, while my brain was going around categorizing things and trying to organize the book, I continued to think that I was following my original strategy. It took me about a day to realize that I wasn’t.


At the end of the second day, I realized that rather than trying to organize a book completely from the bottom up (find an exceptional post, organize other good posts around it, organize those sections, etc.), I developed a framework to organize the posts around, and put posts onto this scaffold.
As I started adding things to the scaffold, I started to assemble some chapters. It became…


You can do it too

  • Humanity
  • Empire
  • People


  • Tracking
  • Travel

Literally, these categories became a mental framework of how the book was going to be organized, with posts placed in their proper place on it.


Perspective Shifts

Even that didn’t last though.


The scaffold kept being rearranged.


After reading some more posts and assembling some more book, I tried to figure out a general vision of the book. I vetted it with Sebastian and the rest of the team, and we all got on board with it.


We decided that we wanted to write the book you would give to your semi-ambitious friends who needed a kick in the pants to get moving. Having a vision for the book changed the game a bit.


I noticed that the Travel section made no sense to include, so I cut it. The introduction wasn’t as powerful as it could be — there was this whole segue in which, after we talked about ambition, we tried to convince you that you could also be ambitious. No good. Why convince people that they should do something even though it’s hard, if we don’t go into why you would want to do the hard thing in the first place?


I kept moving the beams as I realized that they couldn’t be fleshed out, or that they didn’t hold up. I kept looking at and revisiting the material, noticing patterns, developing a new framework, and then trying that out.


This is pretty much Boyd’s OODA loop.


OODA stands for Observe, Orient, Decide, Act. Loop stands for the fact that you do it over and over again.


Basically, you observe your environment, then orient yourself by coming up with ideas that explain what’s happening. You make decisions based on those ideas, and  then act. Your actions influence the environment, and then the cycle repeats.


This happened multiple times in the book-making process.


I observed the posts by archive binging, oriented myself based on categorization, decided what categories had posts for them, then acted by rearranging the posts, and creating a list of posts that made the first cut.


Then I went through that cut and it’s framework, oriented myself by thinking of the general purpose of the book, decided which posts and categories didn’t fit, then acted by rearranging the posts and categories again.


Loop about 2 more times to finish the book, and twice to make the blog, and we’re here now.


Orient is the most interesting step, in my opinion. Without an orientation, I couldn’t figure out what posts were important to the book, or even what ideas were important to the book.


Orientation is basically the step where you figure out what’s going on, and compress the information into something you can think about.


This is a core part of my understanding of strategy.


Sebastian said that Strategy is doing things for reasons.


In order to act strategically, you need to be able to reason what you see in the context of your goals. What does this observation mean? What can I do with this? Does this category make sense, or should I think about it in different terms?


Without your orientation, you don’t really know what’s going on. Yes, we have travel posts, but what should I do with them? That sort of question doesn’t really make sense if you don’t relate it back to something. Without orienting yourself and making your observations mean something, you can do things, but you can’t make them relate to your goals.


You can work, but not win. You can flail, but you can’t act.


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