My Two Worlds (2008), a novel by Sergio Chejfec, portrays a writer who decides to take a walk in a Brazilian city. He uses a map in order to prepare the itinerary and orient himself. While reading Chejfec’s text as an example of a “textual laboratory” about feeling like an insider or an outsider in space, the chapter reflects on how cartography works as an anticipation of reality. Accordingly, maps give birth to a narrative impulse that allows us to geographically imagine a portion of space reproduced on the cartographic support. The map becomes a “door” towards the art of getting lost: in our world, characterised by the ubiquitous presence of GPS, the possibility of wandering in an urban environment and getting lost nearly becomes a privilege. Furthermore, the narrative dimension allows a “cartographic pact” between the map and its reader. Since the protagonist does not use any means of transportation in its urban exploration, cartographic imagination and the practice of walking become the sole forms of knowledge. Thus, Chejfec’s story represents an interesting case study to reflect on the relationships between space and place, territory and its cartographic representations, sense of orientation and sense of displacement.