Thanks for the complement! Hmmm... not easy to think of them. It's not that they're weird, in practice they come off as sounding very normal, but very conservative. I would say the first thing to do is to get to know all of the known cognitive biases surrounding risk because just about all humans suck at it:
Also, read Warren Buffett's annual letters to shareholders and try to emulate his approach to risk. I think he's very good at it.
My biggest problem, after becoming more risk-aware is being comfortable taking calculated risks. I often can come off as a bit of a party-pooper. Nothing says "Life of the party" quite like piling into a cab while hopping from one bar to the next and spending the first 45 seconds of a 5 minute cab ride trying to fish a seatbelt out from under your drinking buddy's ass.
I would say other behaviors that could seem odd to some people are:
* Never play lotto, but always buy tickets for local fund raisers or charity giveaways that have desirable prizes. My wife and I won a week long Black Sea cruise at a charity event where tickets were $10 each but I estimate less than 600 tickets were sold.
* Always buy things like renter's insurance (not likely to be used but will wipe you out if you need it and don't have it) but skip things like those insurance policies they offer at the store for non-big-ticket items.
* I stopped worrying about flying but I've become very pro-bicycle even though I don't bike much at all (because I'm a pedestrian and cars are a bigger risk to me than bikes).
* Pick software frameworks and libraries more based on well-trod paths than the new hotness. Avoid the very old and for the very new, wait a bit.
* And finally, on the other hand: I quit my job, moved halfway around the world, and started a startup in a country that is notoriously hard to do business in (Japan). That would seem very risky but it was the sum of a lot of very calculated moves that seemed like good bets when I took them.
There are probably a lot more. I bet you have some too.
