(there maybe (or not) few spelling mistakes, english is not my first language)
this can be an idea for main "quest" or maybe not fit in game at all, im just leaving my thoughts here.
if its about prison and escaping, you can make days actually count for it. i mean for example if you choose "redrum" it'll be 15 years(?) in prison, so you can "win" doing whatever while playing for 5475 days in game. and lets say work credits can be used to "buy" days: 1 credit = 1 day less in prison.