I am reminded of this passage (Letter XIV, The Screwtape Letters, C.S. Lewis):
You must therefore conceal from the patient the true end of Humility. Let him think of it not as self-forgetfulness but as a certain kind of opinion (namely, a low opinion) of his own talents and character. Some talents, I gather, he really has. Fix in his mind the idea that humility consists in trying to believe those talents to be less valuable than he believes them to be. No doubt they are in fact less valuable than he believes, but that is not the point. The great thing is to make him value an opinion for some quality other than truth, thus introducing an element of dishonesty and make-believe into the heart of what otherwise threatens to become a virtue. By this method thousands of humans have been brought to think that humility means pretty women trying to believe they are ugly and clever men trying to believe they are fools. And since what they are trying to believe may, in some cases, be manifest nonsense, they cannot succeed in believing it and we have the chance of keeping their minds endlessly revolving on themselves in an effort to achieve the impossible.
As for your example, the maxim “you don’t know what you can do until you try” applies. Ask God in prayer whether you are doing things for the right reasons, ask whether your plans coincide with God’s plan for your life, but do not worry that every failure is a sign that you have committed the sin of pride. No, it doesn’t work like that. You can fail for reasons beyond your control and you cannot achieve much if you’re not willing to risk failure. Risking failure is not pride. Risking failure, actually, if a form of humility, because it means you are so willing to be available to God to achieve what God wants you to achieve that you are willing to take the chance that you’ll lose face by even trying it because the whole world will know you tried and the whole world will know you failed. That is obviously not pride.