Merlin has — as ever — some great tips for getting those stubborn, been-there-forever tasks off your list. As well as containing the glorious phrase "plane some cringe off of your hated tasks", which would look great on a T-shirt, he suggests identifying the tasks that make you cringe then trying to work out why.
I've had an embarrassing number of those kinds of tasks that manage to linger on the list for ages, which was the main motivation for planning a feature in Tracks to flag them up. It's weird but I often find that when I do eventually get around to doing those 'cringe items' they turn out to be easy and trivial, and I don't have a clue why I was hung up on them for so long.
On a semi-related note, there was a great Dilbert cartoon today about the work-life balance.