Always be prioritizing

Most of what looks like productivity is the trivial-urgent and the small-known crowding out the important and the uncertain. Prioritizing is noticing which one you're picking, and why.

The default move, when faced with a list of things to do, is to clear the small easy ones first. They finish faster, they look like progress, and they’re satisfying in a way that the big uncertain work isn’t. John Cleese put it plainly:

It’s easier to do trivial things that are urgent than it is to do important things that are not urgent, like thinking. And it’s also easier to do little things we know we can do, than to start on big things that we’re not so sure about.

Both of those are escape routes. They feel like work, but neither is the work that actually matters. The work that matters is the important thing that isn’t urgent yet, or the big thing you’re not sure how to start. Both of those resist getting started, because they ask you to sit with discomfort before they give you anything back.

So prioritizing isn’t really about ranking your to-do list. It’s about noticing which items you’re picking because they’re important, and which you’re picking because they’re easy to finish.

Pick the hard one. Do it badly if you have to. The trivial-urgent list will still be there when you’re done, and it’s fine if some of it never gets done at all.