In this longitudinal interview-based study, I explore the self-assessed preparation, academic experiences, and social experiences of one ninety-one first-generation and thirty-five continuing generation (those with at least one parent a college graduate) students attending Harvard College and Georgetown University between the years of 2012-2016. Through random sampling techniques and iterative interviews, I examine the variation and change over time among first-generation students' descriptions of their college going experiences and compare these to their continuing generation peers. I identify points of overlap as well as factors that specifically affect first-generation students' transition into and experiences of college. I argue that a classification of first-generation students attending elite universities as either "privileged" or "disadvantaged" glosses over the nuanced and varied self-assessments of first-generation students themselves. Instead, I propose considering first-generation students' characteristics and college experiences--especially at highly selective universities--as multiplex, accommodating both privilege and disadvantage, and transitional in both nature and outcome. In short, the first-generation classification is essentially a social category defined by its liminality, not by a durable set of characteristics. Even though the first-generation experience is complex and varied, there are nonetheless policy and programmatic lessons that administrators can draw to support first-generation and all students as they transition into and proceed through college. This dissertation examines the various pathways to thriving as articulated by first-generation students themselves. In terms of academics, these include academic continuation and academic divergence in a field of study, and academic turnaround versus ongoing academic achievement among first- and continuing-generation students from diverse preparation backgrounds. In terms of social experiences, I explore the tactics of bulwarking, pride work, and assimilation as ways in which first-generation students adopt or eschew the classification as an identity feature in a given social context. Finally, I offer specific policy recommendations to administrators aiming not to see their first-generation students make it through, but to thrive in college and beyond. [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/en-US/products/dissertations/individuals.shtml.]