Vaniver comments on How I Ended Up Non-Ambitious - Less Wrong
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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.