This dissertation investigates the interplay of academic preparedness, imposter syndrome, and resilience among low-income male African American students, focusing on their readiness for college and subsequent success. Using a phenomenological approach, the study captures the lived experiences of these students and reveals systemic challenges and psychological barriers. Findings indicate that disparities in academic preparedness, including unequal access to quality education and experienced teachers, significantly impact college readiness. Imposter syndrome is shown to diminish academic confidence and performance, while resilience proves essential in overcoming these challenges. The study also evaluates the effectiveness of support programs like GEAR UP and TRIO, demonstrating their critical role in promoting college preparedness. The research concludes that tailored interventions addressing the unique needs of male African American students are necessary for fostering academic success and equity. Implications for policy include advocating for modifications to ensure equal access to rigorous curricula, skilled teachers, and adequate guidance counseling. This study contributes to the broader discourse on educational equity and resilience in overcoming academic barriers.