I have coined this phrase, "Quicken Guilt," to describe the situation we often see in home offices... We routinely ask a lot of assessment questions in our work as organizers, and one of them is whether they use any financial software. People frequently get a sheepish look on their faces and say they know they "should" be using Quicken or some other financial software to track their spending, but they just aren't doing it.
They are often surprised when I say it's okay not to use financial software. Most people, I am guessing 80-90% of the people we work with, do not reconcile their bank statements either. As long as you have some kind of check and balance on your spending, it's not necessary or realistic to enter in (or even download) every receipt you have and every penny you spend in your personal life. Obviously, it's ideal to use Quicken and I really love their software in general, but it takes a lot of commitment to use it consistently the way it's intended. (I am talking about personal finances here, not business. We feel it's imperative to use Quickbooks or other financial software diligently for any business.)
Online banking has made it more realistic for people to keep tabs on their accounts. We recommend if they are not going to reconcile and use Quicken, they at least need to regularly log in and review their transactions to make sure identity theft does not occur. We also think it's a good idea to make a "snapshot" spreadsheet periodically to look at balances on all accounts and check in with your situation. I am sure not everyone agrees with me on this one... but I know that I have many colleagues in my industry who do. Comments?