How many times must one reconsider?

I still do reexamine my current circumstances and seem to be the only one to, publically, have an original oppinion. That many are based on the established patterns and social norms. Is irrelevant or is it just opposite expectation outcome? They would have convinced me to die when i had everything removed. Despite those efforts. im still not me. Wtf.
Therefore, If looking for an answer and being unable to find/provide an answer to the problem. Given infinite time at what point would u start trying everything even what wont work? Thats why im still alive. Is it really so difficult to doubt/question your and/or humanity's assumptions?