Saving enough from income to pay taxes without any form of withholding is a tough challenge for most people. The self-employed know all about it, and learn the discipline or end up in tax court. As a long-term freelancer, I remember it well. Those choosing to do it for political reasons will find out the hard way unless they are very, very prudent. Somehow, I’m sure that kind of rhetoric doesn’t come with much in the way of prudence.