First Cardinal Sin of Project Management

This is the first (and maybe the last) in a series that I am planning to write on that most horrible, boring, awful, and necessary (but black) art: project management.

(Actually, here’s the second sin.)

First Cardinal Sin
Starting before you are ready.

This pathetic platitude is amazingly often ignored by smart people who should know better (yes, that includes me).

Why? Human nature. We want to feel progress. We want to get going. We want to see some visible results. As Paul Graham says:

In fact, this is a constant problem when you’re painting still lifes. You plonk down a bunch of stuff on a table, and maybe spend five or ten minutes rearranging it to look interesting. But you’re so impatient to get started painting that ten minutes of rearranging feels very long. So you start painting. Three days later, having spent twenty hours staring at it, you’re kicking yourself for having set up such an awkward and boring composition, but by then it’s too late.


In fact, the first parts of a project should not show any visible progress at all. The first parts of a project should be spent on painful, tedious, and critical steps: project definition, specifications, details, outcomes.

Typically, the first answers that you come to when doing the pre-work for a project are the wrong ones.

  1. – First, you don’t know enough yet to get the right answers.
  2. – Second, you’re asking the wrong questions.
  3. – Third, you’re not really trying to find the answers, you’re trying to put an X in some checkboxes, so you’re just going through the motions.
  4. – Fourth, you keep thinking about how great it’s going to be to work on the project, and what it’ll be when it’s finished, and those rose-tinted glasses are impairing your vision.

So. Get away from the keyboard.

Start thinking. Sketch it. Put it away. Re-think it. Draw it again. Iterate until you have a breakthrough.

Now you’re getting somewhere.