Is the "should" you're doing getting in the way of you having the life you want? Is it contributing to you being unhappy? If the answer is yes, then you owe it to yourself to start making some new choices and releasing yourself.
While mistakes aren't a huge issue in my life, I actually spend and waste a lot of time worrying about making mistakes, and also find myself being unnecessarily critical of those around me when they make mistakes (both overtly and covertly).
No one is bad and sinful by nature; rather, we are projecting these characteristics onto the objects we are viewing in this way. Both non-virtuous and virtuous actions arise because of the way we view things, and we have the ability to eliminate ignorant views and replace them with "right view."
What's amazing is that when we consciously release our misery-inducing, controlling ways, we feel better! By this I mean, freer, more at ease, relaxed, and reassured in a manner that can only come from profoundly letting go.