Personally, I cannot imagine not measuring every aspect of my money in every detail: income; expenses; balance sheet; first and second derivatives of same. However, I know more than a few Ps. One of whom I’ve spent a lot of time with, helping to repair f*cked up credit and a miserable future if his ways didn’t change. So, I have a little experience here.

One of the things you have done, a similar thing I taught my P friend is the benefit of knowing what one’s financial condition actually is. It was so bad when I arrived on the scene that he said that on any given trip to the ATM, it was uncertain if any money would be available to him. … Oye!

Getting him to actually do the instrumentation and measurement took a while. Doing it on paper first required teaching him double entry bookkeeping. He hated the chore of the paperwork. I set him on Quicken (for some value of double entry bookkeeping). The automation made things quite a bit better. Once he got comfortable with it, made a ritual of it, he was comfortable with it. The ritual became: sit to Quicken every Sunday morning and just do it. I had him review various reports monthly and quarterly.

At this point, he is solvent, knows his financial condition and has a plan for his future. Although behind in calendar time, there’s time to make up for what time he’s lost.

You can do this too.

1. Don’t use cash, unless you absolutely have to. Use a debit card or credit card (obviously one you pay off every month) from a bank or credit union that has a good online banking website. This way, you don’t have to fiddle with receipts, and can go online to enter stuff into categories if you want, or at least get a summary. While this won’t let you know how much you spent on bread last month, it _will_ let you know how much you spent at grocery stores and such, since it will say “$X spent at Location Y”. Do NOT use a bank that only lets you get online a fixed number of times per month – you should be able to get on it daily.

Simplifying the payment methods you use and being able to look at them in one place will greatly help you to be lazy and still get a handle on your finances.

2. My approach is to “budget” from the “top line”. That is, we pick the amount I feel we should save every month, and if we don’t save that amount, we figure out why and deal with it. It isn’t as precise as fully accounted budgeting, but it’s a heck of a lot easier and doesn’t feel quite as “oppressive”.

3. The most obvious places to target are things you pay every month. A useful exercise is to take those things, organize them into categories (ie, cellphone + internet + landline = total fee for communications), to see how much you spend on various areas each month. If you haven’t done this before, it is likely there is a surprising area in there somewhere.

You would be very surprised just how much of the money you bring in each month ends up going out. If you happen to be frugal then you won’t be too surprised; but if you’re not then you might be. I know that I was.

Good Luck

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o Tax-advantaged accounts
o After tax accounts
o Mortgage and equity estimate

We have about 20 entries for Roth IRA, 401Ks, rollover IRAs, partnerships, e-fund accounts, savings accounts, etc. Once a month – for me, in the middle of the month after my second paycheck – I visit the websites for my bank, brokerage, 401K provider, etc and update all the entries. My spreadsheet is set up so I can track month-to-month changes and changes since the first of the year.

For the mortgage and equity estimate, I use a “hard” estimate from a few years ago from our last house appraisal. I’ve never counted cars and such in net worth calculations, although if you have a carloan, you will need to so you can get a useful estimate.