The purpose of this qualitative study was to explore the underlying non-cognitive processes and institutional factors that allowed first-year students to enact effective strategies for attaining academic success and persisting despite obstacles. The varying levels of academic preparation and unique obstacles faced by the student participants allowed for us to employ a constant comparative approach in analyzing the results. A core story of hopeful thinking emerged which interacted with four major themes including: a) generating alternative pathways when encountering obstacles to social and academic integration, b) goal setting and planning, c) active use of peer and academic supports, and d) experiencing a positive institutional context. While this study confirms research about what factors predict the success of students coping with difficult transitions, it also provides new insights. Results suggest that academic hope is an important theoretical framework to guide future research and practice in the area of student retention.