In the work situation, shyness is generally frowned upon, and people prefer proactive people. Can't say I'm that proactive myself, but I am better at it now, and will try and take the lead if no-one else is able to.
In other situations, yes I'm probably very shy indeed. Like many people here I feel I can talk to perfectly normal strangers, but if I then try and talk to closer people such as my friends and family, the shyness comes out. This happens a lot at parties where I'm with close friends, where I generally shy away and not bring myself to much attention, but it's only when they're not around or after they've gone home that I then really come out of the shell.
The same phenomenon also happens when trying to express my feelings to someone. If it's a stranger who's only going to wash their hands of this conversation later, then fine, but if it's someone I care about... I end up holding back in case I hurt their feelings.
I learned a long while ago that fighting shyness with false confidence is only going to land you in trouble, but I now fight shyness with humour - it's what helped me survive when I moved schools. Heck, I'm so shy I wasn't sure if I was going to respond to this thread. Oh, wait...