Yeah this question is very complex, but actually to be perfectionist in the design stage is sign of lameness, but in a particular way: good design is the fruit

Yeah this question is very complex, but actually to be perfectionist in the design stage is sign of lameness, but in a particular way: good design is the fruit of sacrifice of given things in favor of other things, some kind of engineer-alike-thinking want to get everything at the same time ending with a complex project that's hard to get right. On the other hand good programmers are perfectionists when they actually are writing code. Another sign of smart programmers related to this aspect is that often I saw this good programmers open accepting probabilistic solutions that are good enough even if not perfect if for the kind of problem they are trying to solve this is enough and will work. Less experienced programmers fear this kind of approach because they don't think about the actual result and are not secure enough of their ideas I guess. What is interesting is that there are a lot of times where doing things good enough in algorithms will make it O(N) instead of O(N^2), or in the other hand it can make the code simpler by a factor 10, so this ability is very important.