Weird Al Yankovic's song "I Lost On Jeopardy" was a mainstay of my childhood, I'll admit, but it's been years since I've listened to it, which made this dream a little surprising. In the dream, I was a contestant of some new, post-Trebek Jeopardy which had apparently fallen on hard times. The dollar values were low -- questions were worth maybe ten bucks a pop. I was in second place the entire time until the end. The host was a lady I don't remember recognizing. At a certain point I realized I wasn't answering in the form of a question, but no one seemed to care. And many of the questions were odd--some were yes/no, some were weirdly specific; I remember arguing because the other two contestants couldn't possibly know the answer to some of them. Towards the end, the hostess was shot-gunning questions, many of which I had some idea of but was nervous about answering, since I was in second place and didn't want to lose that. Also, at one point a bizarre couple came in to, apparently, observe us (being 'from the network') but then promptly ignored us. Finally, I answered one of the unfair questions and won.
I'm not really sure about the Jeopardy angle, but I think this is a meaningful dream. I've been doing more and more work for hire gigs, which often consist of several small projects that don't pay that much individually, but when you put them together...so a few cents a word, a few bucks an article, that kind of thing. This is something I've avoided because I never thought I could really make money from it or even do it successfully, and I think the ending of the dream, in which I just push ahead and win, regardless, is telling me to go ahead. Or maybe I should just go on Jeopardy.