Australian higher education participation continues to expand, yet in unequal ways. Regional, rural, and remote (RRR) student participation is stubbornly stalled, despite sustained research and policy initiatives to support these cohorts. To address this complex issue, we interviewed 10 RRR principals in Queensland and Victoria to explore specific challenges that face RRR communities, as well as collate strategies and solutions. Our findings highlighted the importance of leveraging and developing local knowledge and expertise to equip students with careers education, as well as the need to promote a positive narrative about RRR community life. A key theme that emerged from participants was the need to dispel the myth that students needed to leave their communities to achieve their goals or find career success. The findings from this paper point to a need for educational outreach programs to continue to develop context-specific, locally informed programs and support that align with RRR communities' values and ways of life.