The number of Chicanx and Latinx students in U.S. public school settings increased significantly at the close of the last century and continues to increase well into the 21st century. The numbers of Chicanx and Latinx, and more specifically Chicana and Latina, high school principals, however, have remained disproportionately low. Studies that focus on leadership identities of Chicana/Latina school leaders are few. Testimonios in this study shine a light on voices of six Chicana/Latina high school principals; these leaders described their background and schooling, their career journeys, and their leadership paths. This study is informed by two theoretical frameworks: Chicana feminist epistemology (Delgado Bernal, 1998) and applied critical leadership (Cordova, 2018), which insist Chicana/Latina voices are centered and valued. In-depth, semistructured interviews encouraging reflection became the basis for six testimonios that focused on telling participants’ leadership story as authentically as possible using long, unedited quotes to preserve their unique voices. Cordova’s (2018) Mestiza Consciousness Framework provided structure to analyze and uncover themes of duality participants experienced: family as strength/challenge, leading as an insider/outsider, and trauma/resilience. Applied critical leadership principles were used to uncover common transformational leadership traits: leading with a social justice lens, high levels of reflection and self-awareness, and a focus on team-oriented servant leadership.