This short communication provides our insights into how or in what ways educators can more effectively support aspiration of at-risk/high-risk youth toward meaningful education. These are informed by the key learnings from our ongoing youth engagement research. Those insights emphasize the importance of  meaningful engagement of youth  through building a positive relationship with youth from a strengths-based perspective to mobilize youth’s talents into our collaborative engagement efforts in order to effectively support “high-risk” youth and aspire their educational pathways. Conceptually, our work aligns with the paradigms of positive youth development (PYD) and social justice youth development (SJYD). Practically, our research project represents an “anti-oppressive practice” in itself because the project engages youth as important contributors to a social/system change, especially, the role of our youth leaders in our team as a conduit for mobilizing youth views and actions on social justice issues (e.g., oppression, marginalization, social exclusion/inclusion, human rights, empowerment).