If you haven’t started reading the ribbonfarm blog I strongly urge you to consider reading it, because I find it to be on of the most pleasurable blogs right now. Venkats writing is very precise, and he manages to explain even very difficult concepts clearly and easily understandable.
But he is not the only lonely writer to be working on these ideas. There seems to be quite a trend of going into systems thinking and finding ways to incorporate risk and probability into every day decision making.
"The Black Swan" by Nassim Nicholas Taleb started that discussion in popular literature, followed by "Antifragile", by the same author.
But also "The World Until Yesterday" by Jared Diamond devotes a chapter to discuss the topic of risk assesment. And then most recently, Scott Adams published his book: "How to Fail at Almost Everything and Still Win Big", which goes on to discuss the idea of systems thinking on a more practical level.
And to be frank, I feel that I can apply this kind of thinking at a lot of situations. It is as if everywhere I look systems thinking could improve something or indeed does improve things for me already.