I was originally going to post this in GC, but figured it could be intellectual.
That said it will quite possibly be one of the most opinionated threads of all time - and in this case it might actually be a good thing.

Picture this: You have two choices. The first is the choice that would be considered normal to do. You risk nothing, everyone respects you still as you've done what any would. And there's a chance that which you do is tried and tested. Then you have a second choice. That which you feel is the better course of action. Depending on the scenario, you mightn't be risking much, or you could be risking a lot - particularly the impressions others have of you. Your rewards could be any number of things depending on what you've thought up.

This is where the discussion starts. Would you ever choose the second choice? Think of several scenarios following those lines of varying importance including those highly unlikely - if you ever would choose the second choice, where would you draw a line (if you'd even draw one at all)? Perhaps you could even use some of the scenarios you thought up to better explain your thought processes.

Mine will come later, likely the first chance I get a full hour or so to type up an answer without interruption.