As the Semantic Web is increasingly becoming a reality, the availability of large quantities of structured data brings forward new challenges. In fact, when the content of resources is indexed, not just their status as a text document, an image or a video, it becomes important to have solid semantic models which avoid as much as possible the generation of ambiguities with relation to the resources’ meaning. Within an educational context, we believe that only thanks to these models it is possible to organize and present resources in a dynamic and contextual manner. This can be achieved through a process of narrative pathway generation, that is, the active linking of resources into a learning path that contextualizes them with respect to one another. We are experimenting this approach in the PhiloSurfical tool, aimed at supporting philosophy students in understanding a text, by presenting them ‘maps’ of relevant learning resources. An ontology describing the multiple aspects of the philosophical world plays a central role in this system. In this chapter we want to discuss some lessons-learned during the modeling process, which have been crystallized into a series of reusable patterns. We present three of these patterns, showing how they can support different context-based reasoning tasks and allow a formal conceptualization of ambiguities that are primarily philosophy-related but can be easily found in other domains too. In particular, we describe a practical use of the ontology in the context of a classic work in twentieth century philosophy, Wittgenstein’s Tractatus Logico-Philosophicus.