The career experiences of women facing major financial barriers are unique and varied. To better understand and assist such women, the authors interviewed 10 women twice to explore their lived career experiences, using photographs in one interview as stimuli to increase participants' voice and triangulate data. Participants' responses were grouped into 20 themes across 4 domains: career as privilege, reasons for engaging in work, supports, and barriers. Women with major financial barriers appear to understand career as a privilege while experiencing significant obstacles to successfully obtaining work. Participants expressed resiliency and self‐motivation to transcend and mitigate these obstacles. This study indicates a need for increased focus on the career development and engagement of marginalized populations in career counseling theory, assessment, and practice while suggesting practical interventions.