Until a few years ago, my philosophy was to do the hardest tasks first. My thinking was that by knocking those out of the way, you eliminate whatever psychological resistance you have to even embarking on your to-do list.
But a few years ago, when I was working at the video game company Aspyr, our producer always emphasized the opposite route: do the easiest ones first. So any time our team had large bug queues—sometimes 50 or more per developer—we'd always start with the bugs that would take less than half-an-hour to do.
This has a couple benefits. For one, if you do the easy ones first, your to-do list will deflate rapidly to about 20% of its initial size. This therefore eliminates the resistance that comes from feeling overwhelmed.
An added benefit, though, is that the harder tasks may become easier with time. Firstly, because some of the easy things may lead to ways of making the harder task easier. But also because the longer you wait, the more chances you have for ideas to crop up that will make your life easier.
I've often found that strategic procrastination can turn a task that initially seemed like it would take 5 hours into something that takes 15 minutes. For example, there's been a couple times where I procrastinated doing paperwork, and eventually a simple form online or a quicker alternative just pops up out of nowhere.
To-do lists are on my mind, partly because I'm doing errands today, but also because there's an interesting new service, with a cheeky video tutorial, called Teux Deux. (via SarahQB)
