Thank you for providing a moan of despair, right on cue! According to my off-the-cuff hypothesis, this suggests that you have the soul of a CPA. ;) Obviously,

Thank you for providing a moan of despair, right on cue! According to my off-the-cuff hypothesis, this suggests that you have the soul of a CPA. ;) Obviously, my pocket-sized rule of thumb isn't designed for people who earn $100+K per year. Those people can afford accountants. Likewise, people for whom adjusted gross income is a necessarily complex calculation involving the phase of the moon can probably also afford accountants; if not, they need a simpler or more profitable financial plan. Hiring an accountant isn't a particularly difficult thing to do. They're on every street corner. In the month of March, you'll find people dressed in costumes standing at the side of the road, advertising them. [1] And even the robot tax accountant built into Quicken Online was pretty good, in my limited experience. Would Quicken Online have caught the OP's FICA problem? I don't know, but quite possibly. I've never tried to declare substantial quantities of non-1099, non-W2 income in Quicken before, but you'd think it would at least pop up an ominous dialog box. --- [1] A friend of mine had this job once.