This chapter explores working Paulistanos’ access to good jobs and the limits to mobility in the 1920s. By the end of the Old Republic, laborers and liberal professionals comprised São Paulo’s middle class, and a segmented labor market existed with good jobs in commerce, transportation, and the mechanical sector and bad jobs in the textile sector. Interview transcripts and worker profiles show workers valued a high salary, opportunities for training and advancement, and family employment. Established residents and new residents, who were internal migrants, Eastern Europeans, or immigrants from other Southern Cone ports, vied for these good jobs. Despite tightening immigration regulations and increasing cost of living, the city doubled in size. Not everyone had equal access to these positions: a good appearance and the right connections facilitated entry, placing individuals coming directly from the lavoura, who could not afford the city’s overpriced clothing, women, and Afro-Brazilians increasingly at a disadvantage. The search for housing compounded disadvantages, and the working class increasingly built outward, expanding São Paulo’s footprint into the city’s floodplains. The Great Flood of 1929 demonstrated the precariousness of success and limits of opportunity as flood victims sought refuge in the Hospedaria.