Depends quite a bit on how much the "freelancing" brings in, doesn't it? There's a potential self-contradiction to this view that I'd like to tease out. Say yo

Depends quite a bit on how much the "freelancing" brings in, doesn't it? There's a potential self-contradiction to this view that I'd like to tease out. Say you're "freelancing" and doing well enough that you can afford to pay not only the extra self-employment tax, but also to pay full market rate out of pocket for every single benefit that a stable employer would provide. How many clients would you need to make that happen? In my experience, the most successful high-end freelancers - and your comment implies to me, at least, freelancing at a skilled professional level - have a small rotation, or maybe only even one, major repeat client(s). The dynamic very quickly shifts to one of where the freelancer might as well, for all practical purposes, be an employee of those clients or that one major client, right? Except paying more for everything an employer otherwise would pay for.