I'm a bit of a nerd, and do already track probably 90% of my purchases and spending, but I have a bad habit of slacking off after several weeks of diligently tracking my expenditures, causing "gaps" in my spending analysis and worse, "missing" money. Which is really just money I've spent but cannot recall where or what I spent the money on. So for this month, I'll be watching my money like this:
I think here is a good place to mention that I've been using Buxfer to track my income/spending in generic terms over the past few months and I'm overall very happy with it! While there are a handful of improvements on current features that I would like to see implemented (*ahem* multiple account transfer transaction entry and better split-tag-item entries), it is overall a very good and flexible method of tracking your spending. I should say that it does store your information "in the cloud" making some people very nervous. I combat this by using generic terms/abbreviations to de-personalize the information a bit, and I do not use the automatic downloading of statements (though I understand that their plugin stores all account information locally, not in the cloud). I also very much like the ability to export my data to standard CSV/Spreadsheet formats for even further detail analysis not available on the website. In my opinion, it's friendly and easier to use than Quicken -- And does a better job with reporting (though I have to say, I miss the forecast function from Quicken).
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