I like to have my Sims work through a career and try to ascend to the top while creating a family legacy. At least... unless I'm playing a challenge. If it's Family Man, I do whatever fits his aspiration. (Sometimes that's just motherloding all the time) If it's 100 Baby, usually freelance painting or writing.
It all depends on what story I'm telling at that time. I like to try to climb the career ladder just because I like that sense of achievement, but sometimes that just doesn't fit in with my Sims' lives.
