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Another core text is Seeing like a State: How Certain Schemes to Improve the Human Condition Have Failed. The concept it defines is "legibility", summarized in this Ribbonfarm post by Venkat. A legible system is standardized, categorized, manipulable from the top down: the numbered grid of New York City's streets. An illegible system tends to be evolved rather than designed, and makes sense to its users but is hard to explain: the paved cow paths of Boston. The book is about the dangers of demolishing old illegible systems to install new legible ones—a depressingly common historical failure mode. The idea is close to the heart of postrationality, which is more interested in studying seemingly irrational things to see how they tick than it is in optimizing them.
My favorite introductory post is Sarah Perry's The Systems of the World, which categorizes some of her other posts under the umbrella of being able to play flexibly with systems for thinking. Close connections to Chapman's definition of metarationality, here.