Famous pro sports athletes sometimes try to transition from one sport to another. A basket ball player will take up football, or martial arts, or whatever. They don't assume that they'll be successful. Often they'll say it's for the challenge and to expand themselves. This kind of optimism is why they did well in the sport that they were in. They seldom manage in the sport they've joined. That doesn't mean that the attitude is a bad one though.
The world is full of kids who just learned a bit of programming and are making dynamic websites for people. Often this ends badly, as the sites get comprimised or fail under load. But it's a good strategy for learning to program and to make websites.
I'm not good at being an optimist; out of necessity I decided to try. I'm jumping in head first to a pile of technologies that I've been avoiding, and the idea of tackling another code base made my skin crawl. Honestly, the software market is better than the light industrial, retail, etc markets, at least in Phoenix. I know this. I tried. I learned that call centers really have vanished from the US. After the dot com blowout, I worked in a call center for a while. This time, I failed to find such a job.
And, as I chose to ignore, the employer is going to be unhappy. But next time I try, I'll suck a little less. I hit the bottle pretty hard sometimes but I'm thinking at this point I need to explore other drugs that take the edge off of plummeting serotonin levels associated with exploring a new, huge code base. Or I need to transition away from working on large code bases. Branching into any new technology (for me) is going to involve a lot of not knowing.
I have to remember that optimism isn't easy. It doesn't have the predictability that cynicism does. It involves a lot of "I don't know, but I'm doing it anyway". If optimism about ActionScript doesn't pan out, I need to use some towards HP/UX. I've heard stories of idiot sysadmins. An optimist strategy is to think that I couldn't screw up any worse than them.