Orientation, Decision, and Speed in OODA

by Aaron on January 5, 2012

The OODA Loop is pretty useful for thinking about various things. Today I’m going to explain how we did things quickly in putting together Ikigai, through the lens of OODA.


We did Ikigai really fast by publishing standards. In a week to be exact.


When you go through the OODA loop, you observe what’s happening, then orient yourself to figure out what it means. Once you know what’s happening, you can decide what to do, then act.


Assuming you only act after you observe, orient, and decide, the speed at which you can act is dictated by the speed at which you observe, orient, and decide.


The orientation and decision are entirely based pretty much on you. Your emotional state, your analytic ability, the mental frameworks you use, etc.


How do you orient more quickly?


You can copy precedent, apply frameworks from before, become more tolerant of errors, etc. I personally favor developing frameworks during my non-rushed time, but that’s just me.


I can’t say how useful finding precedent and frameworks are. One of the best reasons to study history is to know what’s possible, and how things happened. For instance, most of the transitions between centralized and decentralized information empires were caused by law suits, and I never knew that before. I’m planning a post comparing the historical precedent of other information industries and publishing.


Sebastian has tons of precedent and frameworks behind him, and it shows. I’d be clueless and trying to think through things, and then he’d just email with what he thinks we should do, why we should do it, and a rule he learned from doing things before. One of the most important parts of experience is that it clues you into what’s happening faster than you would be able to if you didn’t know how things ended before.


How do you decide more quickly?


This is hard, because it involves way more emotional stuff.


I think that most people have issues with committing to plans of action. There are plenty of things that will divide your focus and sap your resolve.

  • You’re attached to your current plan of action, even if it’s not particularly working right now. Slowly allowing things to fall apart is often less painful than admitting you’re wrong, for some reason. You can’t look forward because you’re stuck in the past.
  • You’re afraid of what happens if you mess up. You can’t commit to a plan because you’re afraid of failing.
  • You’re afraid of succeeding.
  • You’re afraid of responsibility.
  • You’re worried it will look bad.

How do you beat that?


Having clear goals helps a lot. If you can avoid identifying with your plans and ask the question “Does this get me what I’m aiming for?”, your decisions will happen a lot faster. It doesn’t matter what you think, it just matters what will actually happen.


I relied on this a lot. There were quite a few things I wanted to put into the book (like a chapter about time and Japan), but there just wasn’t the material to tie it together. Since I wanted to teach people, I dropped them. There were some progressions I liked, but since they wouldn’t help an ambitious reader improve their life now, they also got the axe. At times I would be confused about what to cut out, and then I would refer back to the goal and it would be obvious.


Another frame is to just accept the errors, and trust that they’ll be made up for with better data. This is hard, but once you see that strategy work a few times, you start to trust it.


On the project, we were able to do this because we had test readers looking at the book as it was being written. Rather than spend more time arranging the posts, I could just ask Louis what he thought of them. If he liked it, awesome, then maybe a few more tweaks. If something didn’t work, he’d tell me.


There are lots of internal reasons to go slowly.


If you want to beat them, you should probably just buy IKIGAI and read it, there’s lots of good stuff about how to beat it in there, particularly the Growing section.


Observation and Action may be covered in a later post.


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.



Keep your Balance

December 13, 2011

I was hiking in California with some friends, and Jasen Murray said something to the effect of When you’re climbing, you must only keep your balance. It doesn’t matter if you’re at the top of a cliff, or on a branch, or on the ground — the height can’t make you fall over, only losing […]

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Solving Synchronization issues with Thinking

December 11, 2011

One of the awesome things about working on a global team is that you can wake up to nice surprises about things being accomplished. Like, this morning I found out that Sachit and Maneesh talked about designing a landing page, and the general marketing strategy. Also, Sebastian’s friend Yifei could possibly help us with the […]

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Day 1 Update: No Plan Survives

December 8, 2011

I had what I thought was a pretty rocking plan to get the book moving. We’d find the core posts, and start up editing those. While that was happening, we’d find the secondary posts and then give those to the editor. The editor would edit them and send them back to me, and I’d start […]

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The Plan

December 7, 2011

How are we going to publish a book in a week? It helps that we already have a lot of posts to work with. The general strategy is going to be… Figure out what we want in the book, generally. Find the core high-quality posts related to that. Find the auxiliary supporting posts related to […]

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