This article highlights divergent pathways to mobility among members of the new second generation, identifies key mechanisms affecting the choices they make in their pursuit of success, and explains how specific choices were pivotal in determining outcomes of segmented assimilation. First, the authors evaluate definitions of success and pathways to social mobility, advancing a subject-centered approach to study second-generation mobility. Second, the article turns to the results from the authors' ongoing qualitative study of the new second generation in Los Angeles to examine cases that exemplify predictable and anomalous outcomes. Third, the authors zoom in on patterns that emerge from real-life histories to clarify key mechanisms affecting the decisions made by members of the second generation that are consequential in shaping their paths to mobility. The study dispels some enduring myths about group-based cultures, stereotypes, and processes of assimilation. It also advances theoretical debates about intergenerational mobility and immigrant incorporation.