My dissertation "Choice and Inequality in Higher Education" describes the way seemingly benign choices predict course and campus experiences and can perpetuate inequality. I draw on literatures of capital, habitus, identity development, and gender status beliefs and contribute to literature on stratification and sociology of education. I co-designed a longitudinal study of approximately 85 students matriculating in Fall 2019 at an elite west coast university, which I call Western University. The sample generally matches the demographics of the university. I interview these students quarterly to observe how their academic plans, choices, and experiences accumulate over time. In each interview, students discuss each of the courses they considered, their motivations for their ultimate selection, and their experiences and feelings about current and prior courses. My dissertation research uses only the first four panels of interviews (Sum '19, Fall '19, Win '20, and Spr '20). I also have access to 20 years of university transcript and enrollment data, allowing me to compare trends in our sample to the undergraduate population. In the work presented here, my aim was to understand the relationship between university structural/cultural factors and student factors/agency, and how both factors informed the choices students made in their first year. I analyzed three specific instances of students' decision-making in the university context. The first paper, "'Should I start at Math 101?' Content Repetition as an Academic Strategy in Elective Curriculums, " a collaboration with Mitchell Stevens and Philip Hernandez, explores how undergraduates make their first course decisions in mathematics. Drawing on serial interviews (N = 200) of 53 of the 85 students in our study, we show that incoming students with disparate pre-college experiences differ in their orientations toward and strategies when considering first college math courses. Specifically, we found that content repeaters, those who opted for courses that repeated material covered in prior coursework, received high grades and reported confidence in their math ability. In contrast, novices, those who opted for courses covering material new to them, and who were in the same classes as content repeaters, received lower grades and reported invidious comparisons with classmates. Strategies vary with students' socioeconomic background and prior exposure to institutions of higher education, suggesting that content repetition plays a role in maintaining class disparities in STEM pathways. Our findings encourage researchers to resist equating content repetition with remediation, to 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. The second paper, "Offering Safe Passage: Grading Schemes and Enrollment Patterns in Undergraduate Math, " further considers student choice of a first math course. This study takes advantage of a natural experiment that occurred in the wake of COVID-19, when Western switched to all online instruction and mandated pass/fail grading during the Spring 2020 academic term. Using five years of transcript data collected prior to the move to pass/fail grading and comparing it to the 2019-2020 cohort, I find a significant spike in women's enrollment in a first math course during spring 2020. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]