The paper draws on Italo Calvino's acclaimed novel Invisible Cities to describe a few recurrent issues associated with the tasks of describing and modelling reality intrinsic to the use and development of IS. The analysis initially confronts the intrinsic ambiguity that haunts any effort to transform experiential knowledge to a formal representational system. It then moves on to capturing the puzzles created by the establishment of such system as manifested in its potent capacity to describe and model reality, on the one hand, and its inescapable limitations and rigidities, on the other hand. Though these issues have variously been discussed in IS re-search, the literary analysis pursued here casts them in new light that shows the double-edged nature of the task of modelling reality.