I recently realized that I have a stable enough financial position that I should think about saving for retirement. This also made me realize that my relatively loosely structured finances need to be tightened up. A lot. Up until now we just had a sort of spending plan - don't spend more than X dollars on groceries in a week, total up monthly expenses and ensure that they were less than Y% of net income, etc. and the rest just goes into the savings account.
This worked okay, but my dive into personal finance to bone up on investing made me realize that we needed a more rigorous budgeting system if we want to achieve our medium- and long-term financial goals (like paying off my student debt, saving up for a down payment on a house, saving money to defray the initial cost of having kids someday, etc.). We needed a budgeting system that forces us to track every dollar spent and saved (or at least nearly). Our finances being somewhat more complex than I'm willing to deal with all by myself, I went looking for software assistance. My first thought was to try a service like mint.com - you need to trust them with all your online banking logins, but they automatically track your transactions and go a long way towards categorizing the expenses as well. This didn't pan out for us, because mint.com apparently does not play well with USAA, which is where we do much of our banking. This decided me on ruling out online services, as they seem to be unable to reliably retrieve USAA data.
Over at Get Rich Slowly, there was a post on replacement finance software in response to the impending demise of MS Money. This was a treasure trove of leads for me on what's out there. I eventually settled on You Need A Budget (YNAB), and will be trying it out for the next couple months. It is an application that electronically implements a version of the envelope budgeting method, which forces one to account for every single dollar spent. I can download transactions from my various accounts and import them to the program, and it allows me to classify savings in many categories, so this looks promising, but a bit painful to set up at first. It also has loads of online tutorials, but the price is a little steep at about $50. I'll let you know what I think of it after I've used it for a while.