Traditional studies on leadership career have been developed under lineal assumptions, in which a teacher moves slowly up through the school levels, from classroom responsibilities to school headship. In latest years, a growing number of young school leaders have taken the headship of a school, however, little is known about their trajectory to this role. This study aims to fill that gap in literature, exploring the career of Millennial generation public school headteachers. Using a qualitative approach, we interviewed 9 head teachers and analyzed their career considering their life-stories. Even though each story is particular, there was a great convergence in relation to the themes in their career, and we identified 3 central elements: hard work, an openness to learning and a favorable context. Implications to leadership career both at national and local levels are being discussed.