I think that all one need to do is look at the vast majority of my posts here to figure out that I'm a very cynical and pessimistic individual.
Some people view the glass as half full; some view it as half empty. I tend to think that not only is the glass completely empty, it's about to be smashed by a falling anvil.

The good thing about expecting the worst is that you're prepared when it does happen; if it doesn't happen, and things actually do go well and turn out great, you're pleasantly surprised and it makes it even nicer.