The experiences of vicarious unemployment (VU) among 17 undergraduate student participants who had a primary caregiver who was involuntarily unemployed were explored using grounded theory (Charmaz, 2006; Glaser & Strauss, 1967). Data from semistructured interviews with 15 women and 2 men revealed the nuanced nature of experiences with unemployment among those who experience it vicariously. Struggles related to increased family stress and experiences with stigma were common across participants. As participants reflected upon these challenges, they both lamented the costs associated with the struggles and expressed appreciation for the lessons that they have learned. They emerged from their VU experiences with increased financial and job market awareness, which informed their hope for a life that is free from the struggles endured in their families. Participants expressed confidence in their ability to cultivate financial security for their own families, stable employment, and opportunities to pursue work that will allow them to give back to others. Implications for counseling and directions for future research are discussed.