I wouldn't have a biggie size anyway because I am currently working really hard to lose a stone in weight! 
Your question is interesting from what I can get from it but it's hard to read and be sure I understand what you mean! There is nothing wrong with taking a punt and trying to get more but life is a little different because there is often far more options or consequences. You cannot prevent what you cannot predict and life loves to deal you a sneaky and underhand blow.
Many people are out of work at the moment (myself included) and if I were to get even just a rubbish job, I would be thrilled to just be earning more than the meagre amount I currently live on. Once you're on to the next step, your desires and needs change because you're now in a position to be choosey and so on up the ladder. You'd be silly not to make the best of a situation you find yourself in but sometimes when life has given you lemons, you don't have the sugar to make lemonade! Just a thought but happy to discuss it further.