Upward social mobility is often framed in research in ways that may disguise the unique journeys that Women of Color travel in college and as they aspire toward graduate degrees. This assets-based approach to a multisite case study explored how undergraduate Women of Color who aspire toward graduate education viewed the meaning of their potential degrees for their families and how these women described the role of family background relative to their aspirations for graduate study. Findings indicated that for these Women of Color, educational attainment was a form of aspirational capital, cultivating "generational blessings," a vital part of upward mobility. Graduate degrees were part of honoring the obligations they felt toward their families and communities (familial capital). In activating familial and aspirational capital in graduate education, participants were able to bridge the field (social context) of their families and that of graduate education.