Mint

So, even though I am surrounded by very financially fastidious people, I am not.  Despite man January efforts, I never became a QuickBooks user.  (Part of the problem has been their horrible Mac support.  Not being able to suck down my banking transactions always killed my efforts.)  

But in 2000, I started using Yodlee.  At first it really just helped me look at my family balance sheet, and monitor in one place the combined investment portfolio.

But what I have always really needed was a way to track spending against budgets.  Yodlee grew to include this functionality, but I never used it.  Now Mint has taken Yodlee's info and made it really really useful (and pretty).  It automatically groups and aggregates your expenditures.  You can go in and make sure they are correct, put rules in place, and tag items beyond the categories in which they are grouped.  Now I can EASILY track all my spending over time, look at pretty graphs of trends, tag items (useful for business expenses and tax planning) for other reasons, and not spend a ton of time to accomplish all those things.

Mint really is great.  If you want to be more financially responsible, but have never wanted to be one of those QuickBooks obsessed financially astute people, get over to Mint.