As digital humanities projects bring together more data than ever before, ways of presenting and accessing this data are transforming rapidly: text mining becomes more powerful and ‘searching’ and ‘browsing’ become more complex and interrelated. These tools not only help us find what we are looking for; they also shape our paths of inquiry. For this reason, it is important to carefully consider both the ontologies behind the tools (what exists and how can it be ordered?) as well as their epistemological effects (how do classification and representation affect our understanding?). How can we preserve, in a digital environment, the spirit of serendipity and discovery that characterizes humanities research? By asking such critical questions, we hope to forge tools that may generate unexpected results and new perspectives.