I've used Quicken for a long time now and it's the center of how I manage finances at home. There are similar packages on market from other vendors (MS Money, etc) which probably offer similar features, but I've always liked that Intuit stays focused on their market and I love the way they drive revenue (Quicken 2004, 2005, etc, etc). In my view there's a single trick to making Quicken work for you and that's to use financial institutions that support a direct connection to Quicken. Every couple days I'll hit the update button, download my latest transactions from checking, savings, credit cards, 401k, and stock account, and then spend 5-10 minutes categorizing them and clicking ok. It's a lot faster than typing in all the transactions from receipts and in many cases will set the category for you automatically.

There are some really nice benefits to this. One is that you're looking at your accounts every couple days to once a week depending on your schedule and that lets you instantly spot signs of fraud or identity theft. Another is that you can easily reconcile right then to your online balance. When my monthly statement comes in I file it, never needing to do the old fashioned and often painful work of reconciling.

Because getting the data in and maintaining it is about as easy as it can get, it's not a big step to run a report or two to look at spending patterns, figure out much you've spent on pet food, or build a budget and compare actual to forecast. I know there are many ways to manage money, but this has worked for me and it's one of those patterns I depend on.