The philosophy of information (PI) is a new area of research with its own field of investigation and methodology. This article, based on the Herbert A. Simon Lecture of Computing and Philosophy I gave at Carnegie Mellon University in 2001, analyses the eighteen principal open problems in PI. Section 1 introduces the analysis by outlining Herbert Simon's approach to PI. Section 2 discusses some methodological considerations about what counts as a good philosophical problem. The discussion centers on Hilbert's famous analysis (...) of the central problems in mathematics. The rest of the article is devoted to the eighteen problems. These are organized into five sections: problems in the analysis of the concept of information, in semantics, in the study of intelligence, in the relation between information and nature, and in the investigation of values. (shrink)