One thing that really scared me in the past (and still sometimes does) is asking strangers for pictures! With this photo exhibition I'm working on, I've had to gather courage to walk up to random people and ask them for their picture.
It was really scary at first--I thought of all these questions they could ask, but as I did it I was surprised. I don't think I received one rejection in this project. Everyone I asked to take a picture of, they gladly said yes. Some people actually came to me to have their picture taken as I was walking around!
Towards the end of taking pictures for this project, I began walking into random rooms on campus to take pictures--and even then, no one objected!
I think that we need to step out of our comfort zones more often and do things that intimidate us. We will be surprised what might happen! :)