This chapter examines the character and impacts on workers’ lives and strategies of labour market ‘flexibility’ through a case study of corporate food retailing. It expresses the sense of detachment and isolation that these working people come to feel in their experiences with ‘flexibility’. Changes in the local economy during the 1990s have meant a decline of its predominantly manufacturing base, which in the past had nurtured powerful union organisations. The chapter suggests that through these changes, worker subjectivity and attempts to make sense of restructuring also change. Specifically, workers tend to internalise the responsibility for their own survival at an individual level. In South Africa, retailers have also resorted to downsizing to lower wage bills, together with an increasing use of ‘casual’ and subcontracted labour. The impact of labour market flexibility combines a segmentation of workers at work and increasing economic insecurity in their households.