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.