This paper explores connections between Radical Empiricism, a philosophic attitude developed by William James at the beginning of the 20th century, and Empirical Modelling, an approach to computer-based modelling that has been developed by the author and his collaborators over a number of years. It focuses in particular on how both RE and EM promote a perspective on the nature of knowing that is radically different from that typically invoked in contemporary approaches to knowledge representation in computing. This is illustrated (...) in detail with reference to the modelling of several scenarios of lift use. Some potential implications for knowledge management are briefly reviewed. (shrink)