It did get better, eventually

Okay, so after going back to the game, I took a risk on shorting some stock because it was at a real high price. So, I go for broke and short more than I can afford, but with the potential to make 250K, figured that should get me back into the game. However, the next card for that stock had it splitting rather than going down, so I went bankrupt a second time (that's a new record for our group). One of my friends, his wife and my wife all got out of the rate race and just me and another friend were left in it, but then I was finally able to get some traction, got a couple business opportunities that worked out, a duplex and an 8-plex and finally was able to get out of the rat race. Then after running around on the fast track for awhile without anyone finally winning, my wife finally won (she usually does when we play that game, I think I only one once).
So, even if your luck just seems terrible, you can always turn things around. This may have been just a game, but the same is true for real life. Never give up.