This qualitative study explores the perceived barriers to professional advancement among Black Americans who graduated from Historically Black Colleges and Universities (HBCUs) and Predominantly White Institutions (PWIs) in Louisiana. Through in-depth interviews with 36 participants spanning four generations (Baby Boomers, Generation X, Generation Y, and Generation Z), the research examines how educational background, and generational perspectives influence workplace experiences and career progression. The following themes emerged from the analysis: Readiness, Racism, Resistance, and Resiliency. The findings reveal that while HBCU graduates reported stronger identity development and cultural pride which translated to confidence on the job, they faced greater challenges adapting to predominantly White workplaces. Conversely, PWI graduates demonstrated easier acclimation to diverse work environments but lacked the strong sense of identity reported by their HBCU counterparts. Despite generational differences, participants consistently reported experiencing racism, pressure to outperform White colleagues, and lack of mentorship opportunities. The study's implications suggest the need for enhanced workforce development programs, educational reform, structured mentorship initiatives, and systemic changes in professional environments to address these ongoing disparities. This research contributes to the broader understanding of how race, education, and generational perspectives intersect in shaping the lived work experiences of Black American professionals from Louisiana. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]