Cat Boxes, Garbage, Phone Calls

I’m becoming obsessed with doing the most unpleasant (or simply most dreaded) task first. Your mom told you this when it was time to clean the cat box or take out the trash. “You know you have to do it, so you might as well get it over with.” Ugh! So defeatist and non-fun–sounding, right? Yeah, if you choose to think of it that way. But I’m learning to see unpleasant chores and tasks as expressways to the rest of a more-fun and guilt-free day. Merlin Mann tipped us off a while back in 43 Folders:

Seven things - If you’re too overwhelmed to even think about a big system, try this. Get to work early and make a list of exactly seven things that you can do by the end of the day. Each one should take no more than 30 minutes to complete, but try to make it just 10 or 20. Break one big project into seven little ones or just prioritize your clutter. Do the four you least want to do by 11:00, and I promise the remaining three will topple like fat kids. [Italics added.]

Check out that last sentence. Pick the next call to make, the next email to write or the next web edit to post based on whether it’s the one you least want to do. This is a new idea for me — not instinctive as I was raised on Stephen Covey’s First Things First method of ordering and prioritizing your activities based on “importance” or “long-term benefit.” But I’ve discovered that concentrating first on the least-fun tasks helps you get the important stuff done fairly soon anyway. These are the little nagging tasks, those uncompleted next actions you don’t feel like doing that give you opportunities to add value now and usually avoid being bitten in the tuckus later. They’re also the same tasks your manager is guaranteed to ask you about, every time. You’re in a much better spot when you can pro-actively give a status report on an item, rather than sheepishly admitting you still haven’t crossed it off.

At any time of the day, this method gets me started (or re-started if I need help getting back on the hoss) more easily than any other mental trick. Crossing off the biggest bear of a Next Action — usually on paper in my current system, which I’ll have to describe in more detail in another post — can really free up the noggin. All the rest of the items in the list are instantly lightened by the absence of the most ugly. Then you repeat, looking for the next worst task. It’s not always the method I use to decide what to attack next, but it’s always better than sitting paralyzed, not knowing where to start.

I think the most-important-first philosophy still has merit, but maybe more often at the goal- or project-level, not when you’re staring down a gaggle of ToDos and trying to pare them down. Maybe I’ll figure out a way to sort by “unpleasantness” in a future hack of plain-text GTD files or Palm ToDo databases.