In the life of a company and in the life of a person there is a line that gets crossed when it comes to being organized. When you start out in a business basic documentation and good organizational systems are often optional.

To be clear, I am not saying that they should be optional, rather, that from my experience this is just the reality of the situation. There is usually only a couple of people working on something, so they can always ask each other things and the amount information is small enough that people can mostly keep it in their heads. Also, to be more clear, I don’t really think this is the best way to do things, by its very nature it is inefficient. But in a fast moving startup, it is easy to give into the temptation to skip some of the niceties and get to the next project.

But then one day, you start to get close to the Organizational Event Horizon or OEH. The way you will realize it is by the way it feels, it is the feeling of being Spaghettified. In other words, you get stretched beyond what you can handle. Before you cross the OEH, good organization is about being more efficient and getting more things done. But once you have crossed the OEH, organization becomes the difference between success and failure. Important and critical tasks will start to get missed, and the stress of all the different things going on will tear you apart. If you don’t start to deal with the situation before crossing the OEH, failure in inevitable.

How To Handle It?

I feel like at least on the sysadmin things here at Stack Exchange I am starting to feel the pull. To fix this I think the key is to implement a few basic systems for organization that are based on two related principles: The KISS (Keep it simple stupid) and the “stub” principle. The idea behind both of these is to have the minimal amount of resistance to actually start using documentation and organizational systems. The KISS principle is well known. What I call the “stub principle” is something I picked up from wikipedia and Clay Shirky’s Here Comes Everybody:

“…as long as the experts did nothing (which, on Nupedia, is mostly what they did), nothing happened. In an expert-driven system, an article on asphalt that read “Asphalt is a material used for road coverings” would never appear, even as a stub. So short! So uninformative! Why, anyone could have written that! Which, of course, is one of the principal advantages of Wikipedia. In a system where anyone is free to get something started, however badly, a short, uninformative article can be the anchor for the good article that will eventually appear. Its very inadequacy motivates people to improve it”

In short, something is better than nothing, and there is never really an excuse not to at least start a “stub.” Then if someone is unhappy with the stub at some point, they can improve it. The hardest step for many people, actually starting something, is already done.

In system administration, stealing from Tom Limoncelli, I think the best “stub” is usually a checklist for most system administration stuff. So for example I just started one for “Deployment Steps” which doesn’t actually include how to do anything — just what to do. If someone wants to, they can easily add to it later. Other methods include spreadsheets in Google Docs for licenses and IP address lists, and very short “meeting minutes” which just include decisions made at the meeting and things people said they would do.

On the personal side of things, I have started to use the Inbox Zero technique and Remember the Milk for my checklists. Both of these help me keep my head clear and “Inbox Zero” helps me make sure I don’t miss emails. I have also started to try to batch my interruptions by checking email and chat every 20-30 minutes instead of constantly for at least part of the day.

It doesn’t matter if these are the ultimate-super-top-of-line-over-engineered organizational systems, what matters is that they are simple enough to use and get started with so we don’t pass the point of no return.

(P.S. Before you point out all the obvious flaws in my analogy and that I’m mutilating popular physics, please read Miguel de Icaza’s Well, Actually)