[zorrophreak]

Just adding to It, be sure to perform your practice runs on fictitious grounds. When your confidence builds, you can go ahead with the real deal.

Part if the reason I said try stuff with friends and family. This way you have little to not repercussions of stuff so long as you limit what you're asking them. Fictitious and testing environments work well. It'd be an interesting thing to have someone else you know in the realm of social engineering pose as a rep or supervisor to get them used to talking with these people, given the person posing has an idea of how this particular company or whatever would go. It maintains comfort as its still your friend, but gets you used to the type of conversation.