Educational and career transitions among for post-secondary students have become increasingly complex and multi-faceted. Cultural minority students have particular strengths, needs, and challenges when navigating school-to-work and school-to-postsecondary transitions. However, most career transition research and counseling programs adopt individually-focused theories, values, and interventions that may not be relevant for these populations. Our team’s research and student mentoring projects are informed by social constructionist and relational-cultural theory that integrates relevant cultural and contextual factors to support young adults’ cultural identity, mental health, and success in educational and work settings. In this paper, I summarize concepts and issues related to school-to-work transitions from a relational-cultural perspective. I then present results from culturally-informed group and individual interviews with more than 150 cultural minority youth and emerging adults. Issues, options, and interventions to support successful transitions are presented. Six common themes were identified: cultural identity and mental health, mentoring and relational connectedness, respecting diversity, family and community roles, education and work roles, and impact of discrimination. More specific sub-themes included particular cultural perspectives, mental health stressors, and community values. Participant experiences are contrasted to more mainstream or majority student expectations and assumptions related to individuation, choice, affluence, and success. Given our increasingly diverse communities, culturally inclusive theories, models, and curricula benefit all students, even within seemingly similar contexts. Relational support and mentoring were effective cultural practices that were found to support successful transitions and positive mental health. Implications of the research are applied to identity and work development education, research, and practice.