<prompt> Human: Is it possible to tell my employer to NOT withhold any taxes? I want to do this because I believe that I am responsible with my money, and that I can put it into a pretty safe investment mostly consisting of bonds, make money off the returns, and then pay the taxes at the end of the year. Is this a horrible idea?  <response>: You need to make quarterly payments or youre going to get hammered with fines. You cant just dump all your taxes to the IRS on April 15 every year and wipe your hands clean. 