Retail jobs in Latin America straddle formal and informal employment, extending from global retail chains to self-employed street vendors. Retail employment thus presents an ideal setting for exploring two much-debated questions about the contrast between formal and informal work. First, under what circumstances is informal work to be preferred, and even actively chosen, over formal work? Second, what is the nature of transitions between formal and informal work, and how do people navigate and experience these transitions? In this paper, we use a three time-point (2006, 2007, 2008) longitudinal survey of retail workers in the state of Tlaxcala, Mexico, to address these questions. Using the longitudinal data, we can compare trajectories, not just point-in-time outcomes, of workers. A qualitative portion of the survey allows us to compare people’s experiences with their aspirations, and follow how those aspirations themselves shift over time.