Routine, but Cannot be Automated

The hardest kind of activity to get organized is stuff that is routine, but cannot be automated. This is stuff that has trivial meta-content, but non-trivial work content. Even GTD struggles in this department.

Trivial meta-content means it is not hard to plan or schedule this stuff, or figure out and create the necessary enabling pre-conditions. Non-trivial content means the actual work is hard and cannot be automated.

Blogging is an example for me, so I’ll use that. If I had to put it in my organization system, it would simply be write blog post as a weekly calendar reminder.  No biggie. But I cannot put the work itself on autopilot.

Small business book-keeping is another. It seems simple enough to just put your receipts in a shoebox, and update your books based on your invoices, credit card statements, receipts and bank balances every month. All you need is an Internet connection and your shoebox. But the work itself cannot be automated.

Why is this stuff hard to get organized? Is it fundamentally hard? What are the consequences if you don’t keep up?

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Squeakastination: The Opposite of Procrastination

I recently made up a 2×2 that’s proved rather useful. If you classify behaviors based on whether they relate to unpleasant or pleasant tasks, and based on whether we delay doing them or over-prioritize them, you get four classes of prioritization behaviors.


This post is about our tendency to prioritize certain unpleasant tasks too much. This tendency has no commonly accepted name, so I’ve decided to call it squeakastination for reasons that will become clear in a minute. It is the opposite of procrastination, and in my opinion, far more dangerous.

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The Pomodoro Technique

The last few times we’ve chatted, my good friend and fellow time-management-hacker, Erik Marcus, has been urging me to try out something called the Pomodoro Technique (there is a book that’s available free at the website). The idea is deceptively simple: to organize work in 25 minute uninterruptible sessions, with forced 5-minute breaks in between (and longer breaks every 4 sessions), using a clearly visible time signal. The 25-minute session is called a pomodoro (named after the tomato-shaped kitchen timer that the author, Francesco Cirillo, first used when experimenting with the idea).


Reading it, I realized that I’d encountered versions of this idea before (I recall my 9th grade biology teacher making us try something like it back in 1989), but had never stopped to consider the psychology of the idea. I recommend reading the book (it is free like I said, and very short at 45 pages). Here are my initial thoughts on how/why it works and how it relates to the ideas in Tempo. If you’ve used it, I am curious about your take.

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A Pilgrimage through Stagnation and Acceleration

Gregory Rader at just posted an interesting synthesis of the some of the ideas we’ve been discussing here lately. He’s taken elements of a couple of my recent posts, thrown in other ideas, and come up with a deeper explanation of why mindful learning curves, thrust, drag and 10x effects behave the way they do.  He zeroes in on the idea of latent drag/lurking drag (drag that’s waiting to kick in) as the central meta-problem, and gets to several interesting insights.

But, suppose you have perfected the art of schedule management…have you permanently defeated the scourge that is drag?

Of course not.  Ultimately drag is anything that distracts you from thrust work.  Biological needs are sources of drag.  You surely know at least a few people who periodically engage in near-manic bouts of creative effort, largely by ignoring their needs to eat, sleep, or maintain decent hygiene.

Venkat focuses on schedule management because it is an obvious limiting factor.  Schedule management, for many people is the low hanging fruit.  However, alleviating one source of drag will only enable a temporary period of productive acceleration before another, previously latent source of drag emerges as a limiting factor.

For some relevant context, Greg is big on CrossFit training, and I suspect a lot of his thinking is informed by analogies to that transformation process. Read the whole post: A Pilgrimage through Stagnation and Acceleration (and the comment I’ve posted on stuff like moving bottlenecks and weakest-link dynamics).

Thrust, Drag and the 10x Effect

If you are only used to driving cars, it is hard to appreciate just how huge a force drag can be. The reason is that drag increases as the square of speed, so an object will experience 100 times the drag at 300 mph as it does at 30 mph. Not 10 times.

In  Physics Can Be Fun, Soviet popular science writer Ya Perelman provided a dramatic example of the consequences of drag. With drag, a typical long-range artillery shell travels 4 km. Without drag, the same shell would travel 40 km.

Or 10x further. Which brings me to the famous 10x effect in software engineering.

If you haven’t heard of it, the 10x effect is the anecdotal observation that great programmers aren’t just a little more productive than average ones (like 15-20%). They tend to be 10 times more productive. A similar effect can be found in other kinds of creative information work.

Can you transform yourself into a 10x person? If you meet certain qualifying conditions (by my estimate, maybe 1 in 4 people do), I think you can.

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Forgivable Sloppiness: The Art of Epoch-Driven Time Management

I didn’t write a whole lot about time management in the book. This is because I believe it is a pretty mature field and I don’t like reinventing the wheel.  But I do have ideas about how to make your time management behaviors more robust, so you can allow for a certain amount of forgivable sloppiness in how you operate. David Allen of GTD fame once remarked, only partly in jest, that the fastest way to increase your productivity is to lower your standards. Forgivable sloppiness is my term for what it means to safely lower your standards.

The core idea is what I call epoch-driven time management: varying your behaviors based on the tempo of a project.  The idea can be generalized to your whole life, but let’s start with a single project, a thread in your life. This diagram, the Double Freytag triangle, which I discussed at length in the book, is one systematic way to carve up the time-line of your project into epochs with consistent tempos.

For the purposes of this post, all you need is your intuitive reading of the diagram. Think of the cheap trick and separation event as the psychological starting and ending points of a project (if you haven’t read the book, the choice of terms will remain somewhat cryptic, I am afraid). The height of the graph at any given point is, roughly speaking, a measure of how crazy your life is at that point. Each phase of the diagram is an epoch: it has a consistent rhythm, energy level and emotional feel.

Now that we have our terms defined (I am still working on an online glossary so I don’t have to do this for every post), let’s talk about forgivably sloppy time management.

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