Why not convert your "1099 boss" into a real freelancer client? This involves a few simple steps: 1. Ask him to be "upgraded" to a real employee (he'll say no,

Why not convert your "1099 boss" into a real freelancer client? This involves a few simple steps: 1. Ask him to be "upgraded" to a real employee (he'll say no, as we suspect) 2. Tell him you understand his decision, and since he wants you to be freelance, you will work for him as a true freelancer, e.g. for a certain number of hours, at a certain hourly wage, at your own home, at the hours you choose. 3. He may "fire" you. However, if you are as indispensable as it sounds like you are, he will come crawling back to you. In any case, he won't fire you until he sucks know-how out of your brain, which he would do over the course of a month of freelance work. So you have some time to do the transition. P.S. Leading a rebellion is only needed when you have no leverage. In fact, you have tons of leverage, you just don't understand or are unwilling to use it.