Moon, can't you just "switch" and decide that finding a job is a task, make it part of the game? I use to do that with book characters, after I'd finish a good book with a hardworking character, I'd work to do like they did, just try to do what needed doing no matter how afraid or difficult it was. They always have someone come along and "help" them and it often happens that way in the real world too. Look at your T and how she's shown up and been with you? She can be one of the characters in your "real" life roleplaying adventure!