This study examined person and environment contextual factors associated with career decision-making difficulties among Black first-generation students (FGSs) attending predominantly white institutions (PWIs). Using Lewin's field theory, we investigated the predictive value of person and environment factors on help-seeking behaviors for 63 Black FGS attending PWIs. We used a non-experimental correlational research design, along with hierarchical regression analysis, to investigate the predictability of contextual factors on previous career services use and intention to seek counseling for racist career barriers. Change/loss in advisor and lack of information were associated with previous career services use, whereas intention to seek counseling for racist career barriers was predicted by age, gender, interaction self-efficacy, and academic competitiveness within their program. Findings of this study can be used to develop and implement antiracist college counseling and career advising services. We explore implications for practice, include suggestions for policy modifications, discuss the limitations of our study, and finally, provide recommendations for future research.