The author shares reflections based on personal experience regarding the trends, challenges, and dilemmas of educators addressing issues of inclusion and social justice over the past 35 years. Social justice educators need to expand their practice to center the complexity of the intersectionality, simultaneity, and salience of multiple privileged and marginalized group identities. Self-work and healing to minimize the impact of internalized dominance and internalized oppression are critical to the effective use of “self as instrument,” their greatest tool to dismantle oppression. Social justice education must be situated within a strategic, systemic organizational change process to ensure sustainability and impact of efforts.