This article examines how the practices of street vendors in contemporary Santiago relate to changes in their identities, which have been reconfigured along with city’s form and organization under the capitalist economic system. It explores the way street sellers adapt their working practices to a new understanding of their work as maximizing economic returns over all else. As part of this process, they display diverse spatial techniques (to circumvent increased policing, for example), use infrastructure and traffic flow changes for their own purposes, and adapt their public images and organization to the modernization of the transport system. On the basis of ethnographical observation, this article argues that the practices of street selling in Santiago have acquired particular traits from the interrelations between specific elements: The sellers develop skills and attitudes pertaining to the flexible labor economy, such as the ability to adapt to new enterprises and individual ambition, and that these new dispositions reconfigure their identities.