A condition when someone is running out of money due to extreme addiction; living a lavishly-pretentious-hedonistic lifestyle; or involved in cult, Ponzi Scheme, or something similar: having enormous debt, so they sell and/or pawn their possessions just to survive
This term originated from the deep south (TAM^2aUSA). It's actually an acronym representing the following phrase:
"U Gotta Do What U Gotta Do"
You are out at a club having a good time, drinking, etc. A girl starts to give you some attention, but you know that you would never hook up with this girl sober... or even when you are just slightly drunk. Then your friend, noticing what could be going down, turns to you and says "UGDWUGD."