I could not identify with you more.
I am very much like you. Always been rather quiet and a bit awkward. I found solace im being involved in things where I was crearly odd one. That reminds me of your experience working abroad. Alot of my more confident periods were when I was in a serious relationship. That made me feel like a better me. So it gave me conferenceIin the rest of my life. Still it was inly temporary.
I dont have a lot of friends and am not motivated to go out and find them. I like people but more often then not I feel highly uncomfortable in social settings. The friends I have I dont particularly enjoy any more but they are what I got. Same on the career front. I have 3/4 of a BA and no real ambition to finish because I dont want to end up working for the weekend either.
By what I know and have experienced you are right. You / we / anyone needs to just get out there and try. Try and fail and try again. It is discouraging but you have to exept failure as a part of your journy.
What have you take steps towards? The web design idea sounds promising (im actually thinking of the same career, further similarity) Do you ever force yourself to go out some where to meet people? Any social grouls you might enjoy in your area?
Im happy to swap stories and such if it might help you.
Best,
Cory