If you've watched Jeopardy, you may see some overconfident high-rollers, so to say, start at the bottom, meaning the highest points or dollar amount in a given category. But this isn't always a good long-term strategy; you're better off choosing the questions with the lowest points, because you do lose points if you get a wrong answer. As questions become progressively harder as the point/dollar equivalents get higher, you're essentially building a buffer in case the later questions don't go too well for you.