This international, phenomenological study involved marginalised individuals who completed higher education despite their socioeconomically disadvantaged backgrounds. Two subsamples included first-in-family college graduates; 16 Roma professionals in the Czech Republic and 29 Native American academics across the United States. Due to the assimilationist legacy and class privilege underlying the respective educational systems, the participants' education-driven social mobility trajectories entailed particular struggles. However, the participants were able to reinterpret and transform selected factors inherent to the disadvantageous sociocultural contexts of their working class or even underclass backgrounds into sources of resilience. Although the historically embedded sociocultural and political contexts pertaining to each population impacted these sources, patterns shared across participants regardless of their diversity are highlighted. This study develops a deep understanding of crucial interest to educational practitioners and policy-makers. Marginalised minority members can also benefit from learning how differentiated and distinctive meaning systems associated with social mobility trajectories can hinder/facilitate resilience.