Prior to running my own business from 97-01 I knew to the penny how much money I had. I kept a cash box in the house with "petty cash" from which I would use to put money in my wallet. I kept Quicken up to date and had an account for petty cash so I even knew where the cash was going and could chart it. To back up Quicken, I kept an excel spreadsheet that summarized my income and expeditures so at a glance (that Quicken never comfortably gave me) I could see how I was doing. I updated daily.
After 2001 I fell to pieces and have yet to regain a decent grasp of my finances. Today I know roughly what is going out and roughly what is coming in (nothing). It is very uncomfortable.
Well today I began getting things organized in MS Money! Perhaps I won't be so extreme as I was prior to 2001 but I am going to be able to do some decent forecasting and understand where our expenses truly are so that we can plug some holes.