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A survey of political philosophy from Antiquity to present times, and of more recent efforts to create a thoroughly planned society, leads to the conclusion that history does not give an unambiguous answer to the question whether or not macro‐social planning is possible. From an analytical rather than a historical viewpoint, the concept of planning turns out to be ill‐defined and to have many implicit surplus‐meanings that are supposed to distinguish it from similar decision‐related activities, but do not really do so. The planning paradox is inescapable: Perfect planning implies perfect prediction, which in turn implies a deterministic universe that leaves no room for planning. While the cost‐benefit ratio of planning efforts increases during periods of rapid social change, for reasons that are explained, the author nevertheless concludes that a tenacious pro‐steering bias exists as a result of human cognitive dispositions towards balanced thinking, linear thinking, asymmetric attribution of success and satisficing.

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