As adult learners increasingly seek bachelor's degrees for career advancement and personal fulfillment, understanding their unique challenges and experiences becomes crucial for higher education institutions. This study focuses on the academic journeys of nine adult learners aged 29 to 53 who attended community colleges in Florida before seeking a bachelor's degree at one of Florida's public universities. Using Schlossberg's (1989) Transition Theory and Weiner's (1972) Attribution Theory as frameworks, this study examines participants' perceptions of the situational and dispositional experiences that impact their pursuit of a bachelor's degree. The results revealed narrative themes categorized as learning curves, demotivating experiences, and influential factors, including balancing multiple responsibilities, overcoming financial aid policy constraints, and the need for strong support systems to sustain their academic persistence. This study highlights the resilience and determination of adult learners in achieving their educational goals despite challenges. The findings offer practical insights and recommendations for higher education practitioners to better support adult learners in undergraduate programs, emphasizing the importance of tailored student services and flexible academic policies that support their retention.