Rags to Riches challenge??

I've done rags to riches a number of times, but I admit I didn't bother with rules. I just did what made sense for my story. I try to limit my sim to a number of activities. For example, my outdoorsy sim made money through gardening and fishing.... and eventually woodworking as he needed the handiness skill to complete his fishing aspiration.. It would have been too much (and would feel too cheaty) if he also took up painting or writing books in order to make more money.

Also, it's always fun for me to start out my sim with no money and no possessions. He would eventually earn enough for a tent and a cooler, then slowly progress to a house.