Balancing your checkbook is one of those chores, like taxes, that everyone hates but does anyway. Of course, unlike taxes, you slack off for a month and the feds don't come busting down your door. So you slack off for another month...
If you're like me, you have several abortive attempts to use the check register that came with your checkbook to manage your money. My current check register even includes a handy three-year calendar for 2003, 2004, and 2005. The only real use I have for this ancient piece of banking technology is to track when I've overdrawn my account. After each time that happens, there's another 1/4 to 1/2 page of studiously usage until I start forgetting again.
Part of the problem with using a check register is that hardly anyone even takes checks anymore. I write around 30 or 40 checks a year; all of them are for paying bills, so I don't even bring my checkbook with me when I go out. I also don't generally carry cash, so that means a lot of miscellaneous debit and credit card transactions. And, lets be honest, who actually wants to carry a checkbook just to record all of those so they can balance their checkbook at the end of the month?
Of course, one thing I do always have with me is my iPhone. And, as they say, there's an app for that (several of them, actually). PocketMoney is the one that I finally settled on. There's a free trial, so really there's no excuse not to at least take it for a test drive. Training myself to use this was definitely easier than training to use a check register, and the built-in budgeting tools are impressive. When I've got the app handy, "I'll record this $1.40 at Starbucks when I get home" is really hard to justify.
One of PocketMoney's most useful features is the different budgeting schedules. If you get paid bi-weekly, enter that as the repeat period. The program will automatically pro-rate your budget based on how many weeks (or partial weeks) are in the given month. Enter Rent monthly, Groceries weekly, Salary bi-weekly, and Auto Insurance quarterly, and the app will take care of all the calculations to give you correct budget breakdowns by any time range you choose.
For me, though, the real power of this app comes when combined with online banking and online bill-pay. The recurring transactions feature lets you schedule automatically repeating transactions, so you never forget about an automatic withdrawal again. Online banking means that I can balance my "checkbook" against my bank account daily, weekly, or just whenever I remember and have an extra 10 minutes to spend on it. For me, this is a whole lot more convenient than remembering at the beginning of the month when I get my bank statement in the mail. Plus, since I have everything synchronized, I know how much money I don't have and can keep from overdrawing yet again.