Blog to the top
As commenter (and professional film critic) Josh pointed out, not all blogging leads to one being turned out barefoot into the snowy wilderness. Of course, I expect that there are many Tesses for every Kevin Drum.
Rude Pundit shows the way to do it. He's launching a one-man comedy show in NYC using his blog for material and pumping his readership for advertising dollars. All while remaining anonymous. Good on him.