Note: While I think this is a good idea, it's clear that many readers strongly disagree. Before deciding whether to try this, please read the arguments in opposition.
Earlier this year, on a whim, I did something a little odd: instead of just paying my monthly cable and internet bills, I wrote large checks, pre-paying for several months of service. I didn't have a reason for doing it at the time. I had a momentary surplus of cash, and it seemed like a good way to use it. Maybe I ought to have tucked it into a high-yield savings account, but it seemed just as good to me to pay five or six months ahead on these bills.
As it turns out, I love this. I know I'm not paying any less money than I normally would, but by pre-paying my bills, I feel as if I don't have them. I feel as if I'm getting my cable and internet for free. In fact, I'm probably going to write checks at the end of December to cover each of these bills for all of 2008.
Some of you will shake your heads and decry the absurdity of this notion. That's fine. This sort of money mind game isn't for you. But if you're the sort who gets tense from a stack of bills, consider giving this a shot. The next time you have a small cash surplus, prepay three or six months on your phone bill. See if it makes things easier.
(In a way, this is a low-tech path toward paperless personal finance. It's not actually paperless, but it has the same effect — it decreases the number of things I have to bother with each month.)