So, I just recently found out that I'm supposed to be paying my taxes quarterly since I'm a sole proprietor. I tried to read the directions on the IRS website and it's making my head spin. Does anyone here do this on their own? I don't really want to spend money to talk to an accountant. Actually, I'd rather not pay any taxes at all. How hard (and safe) would it be to deduct business expenses so I wouldn't have to pay any taxes? My only real business expenses are web hosting and domain registration. Could I start including all everything I purchase, like clothes, gas, food, and even my college tuition? I'm going to be making a lot more than I spend this year though, so I wouldn't be able to completely eliminate my tax liability, would I?