When I was in high school, I was in a media arts class where we got to learn how to use video cameras and make little movies. Before we went out to make our stunning directorial debuts, our teacher gave us a very valuable lesson that I still remember today. He told us that if we wanted to film somewhere and needed permission, never be afraid to ask. He simply explained:
"The worst they can say is 'no'"
My little movie crew and I went out to a gas station and asked the attendant if we could film in the store and he very nicely told us that he wasn't allowed to let us do that.
At 16, that was really enlightening. Once we had the answer, we knew that we needed to get resourceful and find another solution so we did. The great thing about receiving "no" is that you don't have to worry about guessing that person's feeling about something. "No" frees you from wondering if you should continue down a certain path or find another way to achieve something.
Even today, as an adult, it's easy to try to dissuade yourself because of what you might assume a person's answer is going to be. But the key lies in realizing that the answer can't hurt you.
"No" really isn't that bad. Receiving "No" is sometimes the best thing that can happen to you because then you know that you need to go about getting what you want in another way. In the last year, I don't really remember the "No's" I received and they didn't cost me anything.
So go get out there! Ask for that promotion, ask to partner up on jobs, ask for your lead's business, ask for a discount, ask for feedback, ask for help. You won't know their answer until you ask. If you get "No", then learn from it, move on, and find your way.
And here's the best part of all learning to ask: sometimes they say, "Yes"