As higher education institutions make intentional steps to include underrepresented groups and ensure their success in school, it is particularly important to understand their epistemological, intrapersonal, and interpersonal development as a key factor of supporting their academic and developmental needs. Institutions of higher education are challenged to prepare graduates for engaged citizenship in an increasingly multifaceted world that requires college graduates to demonstrate higher-level order epistemological abilities to successfully navigate in the 21st century. This qualitative study investigates self-authorship theory through the perceptions and experiences of first-generation undergraduate students, contextualizes periods of cognitive dissonance, examines contextual and environmental factors related to development, and frames these experiences as catalysts that promote self-authoring behaviors. This study captures the unique stories of 14 first-generation undergraduates at a public 4-year comprehensive liberal arts institution on the West Coast of the United States. Future research and practical application strategies to promote self-authorship are provided for higher education professionals to intentionally design supportive learning environments in an effort to better serve the developmental needs of first-generation undergraduates.