Stop me if you've heard this one. At every time management training ever, someone brings up the analogy of a jar with a pile of rocks and sand, and emphasizes that you have to put the big rocks in the jar before the sand, as an allegory of prioritizing tasks.
Here's the problem with this analogy: it makes the presumption that size of task is the only priority. The reality is that prioritization of things happens along more than one dimension. The three dimensions of prioritization I use are urgent, important, and efficient.
Urgent is fairly obvious. How soon is something due? All other things being equal, take care of the thing that's due first. That said, rarely are all other things equal.
Important is also fairly obvious. How important is a task? You may have two tasks that are urgent, but only one of them has any importance. For example, you might have a million dollar programming contract on your desk, and you might also have an internal request to change the color of the corporate intranet to be lime green. Both are due in a week. One of them matters.
The last dimension that is less obvious is efficient. This is what the analogy of rocks and sand supposedly addresses, that you want to tackle the big stuff first, then the little stuff, so that little stuff doesn't fill up your day. The reality is, however, that the more stuff you have on your plate of any size, the more mental bandwidth it consumes. Eventually you end up feeling overwhelmed and nothing gets done. If you have a choice between getting 5 things off your list of moderate importance, or making 5% headway on the really big thing on your list, depending on the other two factors of urgency and importance, it may make more sense to burn down the 5 things.
Most time management systems narrowly focus on one of the factors above. Consider revamping your task management and time management to take into account all three.
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