I agree, it's not inevitably going to be useful. In my case, I was spending so much time planning my games out that I was no longer having fun, so I started to wonder why I didn't put forth the same optimization efforts in real life. Explicitly trying to transfer the optimizer mindset might help ("Here's a decision about my life I have to make. Oh yeah, I remember, making decisions is fun!")

Railroad Tycoon II might be a better choice for making money in particular–you can fantasize about how if you actually were alive at that time and you had $10K in capital, investor connections, and railroad knowledge you could have made a fortune too. Then after playing the game for a while, you could start looking around for equivalent present-day opportunities. (Did you know that at one time, railroad stocks made up over half the value of the US stock market?)