As far as I know * , you can write off your personal health insurance premiums as expenses on your taxes when you're filing as a sole proprietor or an SMLLC (an

As far as I know * , you can write off your personal health insurance premiums as expenses on your taxes when you're filing as a sole proprietor or an SMLLC (and I assume something similar under S and C corps). So ... at least that's a ~30% discount. * Based on a little research I did; I'll find out for sure next April :P P.S. Another nice thing about going solo is your 401k. You can set up a Solo 401k, which has a MUCH higher contribution limit. 401k through employer is limited to ~14k, while a solo 401k is up to something like 50k. Plus, you get to pick your 401k provider, and as far as I could tell Solo 401k through Vanguard was _significantly_ better than the criminal fees I was subjected to under my previous company's 401k. This is all assuming your side business is successful enough to fill that extra 50k bucket :P