So far so good: we understand the need to break down the big things into a set of smaller, actionable tasks. However, how small do we go? How granular should we break down a task for our to-do lists? My opinion is that we should split big activities into a subset of actionable tasks based on how long these actionable tasks will take to complete. Specifically, for the sake of a to-do list, an actionable task should be something that can be completed in a single session.

A session corresponds to the typical length of an uninterrupted period in a given context.  In the office, you might be able to count on one hour of time before you could be interrupted by meetings, phones, or colleagues.  It might be as long as the entire workday if you don’t usually get a lot of phone calls or interruptions. However, in the office a session could never be longer than one work day! For tasks in your house, a session might be more like 30 minutes. A session is the amount of uninterrupted time you can usually count on in a given context.

Why should we engineer it so that our actionable tasks can be completed in a single session in a given context?

1. Because once you start it, you can finish it and therefore partially completed tasks do not litter your to-do list.
2. Because you will always complete something you always have a sense of progress and accomplishment.
3. If it will take longer than a single session, you probably have not thought through the activity in enough detail, and what is involved in completing the overall task. So it is a good check.
4. It eliminates a desire to put off or procrastinate on the “big things” because, well everything and anything on your to-do list fits into your working time.

Joel Spolsky provides excellent advice on creating task lists for software development projects that is equally applicable to just about any to-do list:

Pick very fine grained tasks. This is the most important part to making your schedule work. Your tasks should be measured in hours, not days. (When I see a schedule measured in days, or even weeks, I know it’s not real). You might think that a schedule with fine grained tasks is merely more precise. Wrong! Very wrong! When you start with a schedule with rough tasks and then break it down into smaller tasks, you will find that you get a different result, not just a more precise one. It is a completely different number. Why does this happen?

When you have to pick fine grained tasks, you are forcing yourself to actually figure out what steps you are going to have to take…These steps are easy to estimate…because you’ve [done them] before.

If you are sloppy, and pick big “chunky” tasks… then you haven’t really thought about what you are going to do. And when you haven’t thought about what you’re going to do, you just can’t know how long it will take…

Here’s another reason to pick fine grained tasks: …By being forced to plan ahead at this level, you eliminate a lot of the instability in a … project.

Source: Joel On Software. 

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