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RE: Why Be A Skeptic In A World of Possibilities
I think what you do (finding faults in the system and stuff like that) cannot be called skepticism. I think it is called "having an eye for detail" and using that to make sure things work right. Skepticism (for me at least) is being dismissive of an idea, mostly without even going through all aspects of it (which is what usually happens).
Even if the what ifs are being asked in a somewhat negative context, I say, we should still ask the what ifs. Because, only after that do we begin looking for further answers.
'Having an eye for details' and 'finding faults in the system' are well described, but unfortunately majority of people generalize that (wrongly) as one being skeptic - with a specifically negative tone. While also cultivating negative tendencies towards that for various reasons:
-they don't have an open mind and can't stand criticism (especially over their own ideas);
-they don't see the details and the path to where those details potentially lead (it takes one to know one - it's hard to explain to someone that doesn't see or understand it);
-majority aspires towards putting in least possible effort as possible to some idea, especially some product;
-...
I fully agree, 'what ifs' and 'whys' are one of most important questions, often eye-opening and leading to invention, innovation, development, progress. It's all about stepping out of one's comfort zone and taking life (and future) in own hands.