The best money I've ever made, and the most comfort I've ever had, was "betting against the USA." In December 2004 I took my retirement fund out of bonds and threw it all at emerging markets funds, FOREX funds and every other aggregate measure I could find that basically said "foreign economies are going to grow faster than the US economy." It was partly luck (my knowledge of the world is imperfect) and partly skill (my knowledge of geopolitic is greater than my knowledge of individual companies' performance) and it paid off about 70% over three years. In September 2007 I took my retirement funds out of emerging markets and forex because I no longer felt that anyone could predict the general direction of the market; the research I had been doing predicted the collapse of the housing bubble but not much else. I responded by putting my money in a ratcheting index fund, so when the S&P dropped a month later I didn't lose a dime. It's still there. It's safe to say that I'm much more interested in "not losing money" than I am in "making money" which I recognize as an excessively-conservative policy for a 37-year-old. However, I just don't trust any system in which public opinion trumps data.
I do enjoy making small investments like my aforementioned short on gold -but even that was only 1k which is really just a way to put my money where my mouth is. I suspect I'll make a similar bet on china, but we'll see. Most of my non-401k assets are still sitting in interest bearing accounts, but I've been nervous to actually invest them - it's hard to gauge which way the market is right now.
Now I want to build a chicken tractor that has very slow solar powered wheels. It would be fantastic if you could program it to drive, back and forth, back and forth, over a large stretch of lawn. Maybe moving a couple of feet per day.