After having agonized over this for a while, I have started to make plans about quitting my job and retiring (or at least take a couple of years off). To briefly describe my situation, I have about 1/3 of my money in IRA accounts, and the remainder in equities (stocks and mutual funds) that produce some dividends. Right now, all my dividends are reinvested. Although my dividends are not enough to allow me to live, I can liquidate some equities as needed to maintain my lifestyle. Is there a "good" way to do this (ie, a strategy for liquidating assets so the most productive are liquidated last). Also, should I stop the drips? Finally, what is the situation about getting financing for a car if one doesn't have a job (but do have the resources to pay cash, if necessary)? I'm hoping to do this in September and realize that I'm not totally clear on the details.