[femto]

As you're alluding, half the battle with knowing when it is "safe" to hop off the treadmill is having a very good idea of your expenses. About 10 years ago, I spent a year or so recording how I spent my money to the cent. I found that it delivered a lot of freedom, even if I didn't live frugally, since it allowed me to know exactly how much money I would need going forward, and plan accordingly.

Since then. my life has changed a lot, to the point where the confidence in predicting my expenditure is wearing off. I'd describe it as a slightly panicked feeling of having to work harder, since I'm trying to cover the worst possible situation that my mind can invent. I probably should invest the time to collect another set of hard data...

[gknoy]

Have you considered joining Mint, using plastic for your purchases, and considering cash as "already spent" expenses? (Stay out of debt, mind you -- use the cards as a way to ensure that it's accounted automatically.)