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Peacewise comments on How I Ended Up Non-Ambitious - Less Wrong
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I consider myself lucky, because making money is what I intrinsically want to do due to all the turn-based strategy games I played as an adolescent. Fuzzy life goals like "find what you like and make a career out of it" don't really appeal to me--in practice, what I like has changed too often historically, and besides, there's nothing to optimize and no rules to game!
Alpha Centauri is an almost perfect example of a computer game that teaches optimizer thinking:
http://www.amazon.com/Meiers-Alpha-Centauri-Alien-Crossfire-Expansion/dp/B003NMA3DG/ref=sr_1_1?ie=UTF8&qid=1327214061&sr=8-1
Unlike the civilization series, the designers decided that since the game was based in the future, they would throw in all kinds of crazy stuff. This gives a big advantage to players who read through the entire manual and develop strategies like "I won't have to deal with drones if I build punishment spheres everywhere, but then I won't have any scientific research. So I'll have to probe the hell out of the other factions in order to steal their advances. Hm, the Believers would be perfect for this, since they're terrible at science but that won't matter." My brother and I have spent hours talking about the game and bouncing strategies like this one off each other. Did I mention that it's insanely fun and addictive?
I played Alpha Centauri for a few weeks back when it came out, ended up going back to Civilisation, more out of habit I suppose than anything else. These days I'm playing Civilisation IV Beyond the Sword.
What is interesting about being taught optimizer thinking within a computer game is that if that thinking stays within the game, then it's not real world applicable as optimal. If however one stops playing the game and then takes the learned strategies applicable in the real world, into the real world - then gaming is useful, otherwise gaming is just entertainment. I love gaming, don't get me wrong - it's just that (simplistically) x hours of gaming translates into x hours of missed revenue/earnings in the real world, or x hours of real world knowledge unlearned.
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?)
That thought helped break a friend of mine out of a Farmtown addiction. Iirc, she was considering making a spreadsheet for Farmtown when the light dawned.
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.