This paper looks at the stories shared by Latina school leaders regarding their ascendance to the superintendency in New Mexico. The social, political, and cultural supports and challenges that they experienced along the way to their top positions in school leadership are discussed including the impact of gender barriers, power differentials, the value of their trusted networks and mentors, and maintaining a sense of mission and direction for themselves and their districts. Authors employed a qualitative portraiture design to ensure authenticity of voice and critical race and feminist frameworks to commit to a vision of liberation in learning and leadership.