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Vaniver comments on How I Ended Up Non-Ambitious - Less Wrong
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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?)
The best lesson I got from the Railroad Tycoon games was pausing at the start, carefully inspecting all of the cities, and finding the 3-4 best pairs to set up routes between, then snagging those before the AI could. (The AI would politely wait a minute or so for you to move first, then start building, and if you built a station in a city they wouldn't. So you set up the best one as a route to make money off of, claim the others, and then they only have terrible routes to pick from, and so stagnate while you grow massively.)
That sort of strategy doesn't work well in real life, but the meta-strategy - know your environment and plan carefully - is rather useful.