In this article, I am examining the role of categorization in understanding. The problem arises from well-known distinction between explanation and understanding, which has been for a century pursued in hermeneutic tradition. Categorization belongs to explanatory endeavor and its role in understanding is unclear. In order to delimit the scope of inquiry I am focusing on the weakest kind of categorization, so called categorization ad hoc. I am examining the hypothesis to the effect that categorization plays its role in hermeneutic circle as some sort of preunderstanding. Eventually, however, I reject this hypothesis. It is because it leads to hermeneutic paradox: The notion of pre-understanding has a meaning only in the context of full-fledged understanding, which is an unattainable ideal. Such ideal cannot be used as a personal criterion of the quality of one’s understanding. There is a tension between the feeling of understanding and the scarcity of personal means to justify this feeling. I am suggesting that similar, albeit weaker effect occurs also in more elaborate, scientific categorizations. What is really wrong in the passage from categorization to understanding is some form of self-understanding: We do not know whether we understand better, or at all when we put some categorical order onto our experience. We do not seem to have the required meta-understanding.
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