When breaking a large project into tasks, there are better and worse ways to go about it. A pretty bad start is picking tasks that are the wrong size – they’re still too big, and require further breakdown.

So what’s a good size for a task, and how can your own description of a task tell you you’ve supersized it? There are a few ways to think about it:

• A task is any goal that you can state with no vague or all-encompassing words. Vague words are ones like “various” and “some of”; each of these is hiding multiple tasks – one per item. All-encompassing words are ones like “all” or “research” (research is a career path, not a task; break it down to what you actually need to do to get from your current state to the learned state).
• The vaguest of vague words, worthy of their own bullet point, are “rethink”, “redesign”, or “re-any-word-that-means-changing-an-existing-thing”. If you’re changing something, your first bunch of tasks are all about understanding the current state of it: What were the choices that went into it? Why was each one made? What’s changed or has been learned between then and now that justifies changing each decision? Should any of these decisions be left alone? What new constraints exist? That’s so many tasks right there, and you haven’t made a single new decision yet! The gap between your starting point and a new design is Sahara-sized. You need a map.
• A task is any verb that doesn’t contain a secret list of more verbs. If “write” actually means “draft, write, edit, finalise, and publish”, you have a problem. If it also means “research”, please see my earlier rant about that word. “Decide” is another verb that can hide a list of three weeks’ worth of extra verbs.
• A task is anything that doesn’t freeze you like a deer in the headlights. This is a gut-feeling parameter; if you’re unsure how to start or what the steps are, that’s a good hint that the task is in reality multiple, possibly ill-defined, tasks. A common word that triggers this feeling is “write”, when it means “turn this blank page into 5,000 words of wisdom”. Even if you’ve already done the research and have an outline, and can reasonably argue that “write” means “write” and not “do all these other things first” (a hidden list of verbs), you probably want to break it down into multiple writing tasks, possibly by following your outline. “Write section 3 of 12” is much less intimidating than “Write 5,000 words”.

Quick tip to conclude: If you can estimate tasks very well, you may be able to tell a task is too big because it doesn’t fit in your attention span. If you work in 90 minute blocks, a task that takes 120 minutes is too big.