It's definitely a fine line between taking a "bottom-up performance" mindset and a "premature optimization" one. Way too often, I'll start approaching something with a fast-complex solution, spend some hours on it, run into major bugs, and then quickly turn around, do the simple thing instead and usually get it done in under half an hour.

I have the feeling that I can only really overcome this by knowing the domain well enough that I don't feel the urge to take on such big problems anymore. It seems like there's a vast middle ground of knowledge where you know enough to not be naive, but you don't know enough to understand what you're getting into with the harder solution.