This study was an investigation of the predictive value of perceived career barriers and career decision self-efficacy on the certainty of initial career choice among low-income pre-freshman college students, an under-studied college population with respect to career development (Winograd & Shick Tryon, 2009). The moderating effects of certain cultural characteristics (race, gender and college generational status) on the certainty of initial career choice were also examined. A non-experimental correlational research design was utilized, along with a multiple linear regression analysis, to investigate the predictability of perceived career barriers and career decision self-efficacy, directly and as moderated by the cultural characteristics of gender, race and college generational status on the certainty of initial career choice among pre-freshmen low-income, first generation college-bound students.