How do undergraduates make their first course decisions, and are these decisions fateful? Drawing on serial interviews (N = 200) of 53 students at an admissions-selective university, we show that incoming students with disparate precollege experiences differ in their orientations toward and strategies for considering first college math courses. "Content repeaters" opt for courses that repeat material covered in prior coursework, whereas "novices" opt for courses covering material new to them. Content repeaters receive high grades and report confidence in their math ability, whereas novices in the same classes receive lower grades and report invidious comparisons with classmates. These strategies vary with students' socioeconomic background and prior exposure to institutions of higher education, suggesting the role of content repetition in maintaining class disparities in science, technology, engineering, and mathematics (STEM) pathways. Findings encourage researchers to resist equating content repetition with remediation, attend to the agentic and social-psychological dimensions of academic progress, and recognize that elective curriculums create conditions for the performative reproduction of academic and socioeconomic inequalities.