Recent institutional and cultural changes have allowed individuals to gradually (but persistently) follow more complex, less uniform, and less predictable work and family patterns than the patterns often assumed to be the norm in Western settings. However, we identify important gaps in this literature: (i) a persistent focus on high-income countries in Western Europe and North America, (ii) an emphasis on narrowed periods of adulthood, and (iii) a disregard for coresidential histories when analyzing the family domain. In this paper, we aim to address these shortcomings in two ways. First, we identify lifetime employment and coresidential trajectories of individuals living currently in Santiago, Chile, born between 1944 and 1954—a cohort that faced several political, economic, and cultural changes across their lives. Second, we explore how gender and socioeconomic disadvantages are associated with individuals’ life trajectories. We conduct a multichannel sequence analysis of a comprehensive life history dataset and find that about a quarter of the sample (27.2%) follows a modal pattern of continuous formal full-time employment and coresidence with a partner and children. The remaining proportion of individuals follow more complex, unstable, and interrupted patterns, which vary in their levels of work attachment, work informality, solo parenthood, and intergenerational households. Our findings question the idea that socially advantaged individuals opt for more complex life courses and instead confirm the association between socially disadvantaged individuals, particularly women and those lower educated, and complex trajectories. Rather than deliberate individualistic choices, life course instability appears as an additional layer of social disadvantage.