Thanks Katiebug, I love your screen name.
My guess, generally speaking, is that folks are either born the self employed type, or the get a job type. It seems less a matter of making a decision than discovering who you are, and making peace with, accepting the what is of, the pros and cons of that lifestyle.
I've been self employed a long time. I've made more in one day than I thought I'd make in a lifetime, and years when I worked like a dog and arrived at the end of the year with nothing to show for it, except a pile of bills. I'm not sure one enters this world based on logical analysis, you either just have to go there, or you don't.
So, another guess is that those who were born to be self employed won't have to figure it out. One day they'll just be overcome by the urge to break out of the squirrel cage, and they'll chew on some corner of the cage 56 hours a day until they're free. Rapture follows the escape, and then the realization you're free to starve too.
Final guess is that a truly free person will be able to make themselves comfortable in either world, even if they wind up on the other side of the fence from their predispositions. So that's why we're here on this board, eh?
Give me chocalate, Now!