There are many illusory fears that will melt under analysis. When you find something difficult for you to do, ask yourself, "What exactly am I afraid of?" Often you will find that your fears have no basis in reality. In other instances, there might be a slight loss, but it is actually quite minor and trivial.
A similar question to ask is, "What is the worst that could happen if I say or do this?" Often, your answer will be, "Nothing much."
Another question is, "How probable is it that I will actually suffer if I say or do this?" When you ask someone for some information or even to buy something, the worst that will happen is that the person will refuse to give you the information, or he will refuse to buy what you are selling. If you wouldn't have asked, you are guaranteed not to get the information or the sale.
So when you ask, the worst-case scenario is exactly the same as if you wouldn't ask. Asking has the potential for improving the situation and you have nothing to lose.
(From Rabbi Pliskin's book, "Courage")