This is a good philosophy for Perl. It's not so good if you're in the cockpit of a military aircaft, wondering what that big red button does ;-).

Much depends on whether you can afford the luxury of "trying it to see". If you're constantly under tight deadlines, you may just need to get the thing done, do it the way that works, and don't ask too many questions about the 'how' or 'why'. The amateur has a slight edge here - s/he can take the time to try it to see. OTOH, the pros often have each other to ask, so maybe it's not such an advantage after all...