In contrast to modernist models that conceptualize schooling as a cumulative process of sequential learning, the school experiences of urban students were characterized by temporal disjunctures (i.e., being retained, failing grade level assessments, incarceration, leaving school). Lemke’s (2000) construct of timescales explains the ways students draw upon the past, present, and future as they make sense of their experiences and define themselves as learners and literate people. The construct of timescales (Lemke, 2000, 2001, 2005) captures how people recursively and selectively draw on experiences across time. These case studies involve eight urban students and their families over an ten-year period via “periodic restudy” (Saldaña, 2003). Data included interviews with children, parents, and teachers; classroom observations; fieldnotes; literacy assessments; and writing samples. Analysis involved four separate and lengthy processes of transcription, coding (Strauss & Corbin, 1990), and analysis over a ten-year period spanning four research phases. Tensions between expected linear and sequential expectations and the lived experiences of students were documented and examined. Each student believed that success in schooling was contingent on fulfilling established linear trajectories. Students made sense of their experiences and constructed their identities as they recursively and selectively drew on past experiences and contemplated the future.