This study identifies how a teacher's entrepreneurial behavior (TEB) changed when promoted to higher positions in a school. It distills her experiences over time to uncover the symbiotic relationship between teaching and administrative entrepreneurial behaviors in promoting school innovation. Drawing on data from semi-structured interviews with teachers in the school, the results indicate that her TEB shifted from self-empowerment via school innovation to empowering others as she gained administrative authority. As a classroom teacher or subject head, the focal teacher developed ownership of innovation advocacy as a teacher leader, exhibiting resource-seeking behaviors and taking risks to spearhead change within her sphere of control. She faced an 'innovation cliff' when she transitioned to a school leadership role and acquired administrative authority. However, she eventually succeeded in scaling up whole-school entrepreneurial behavior and innovation as a school principal. This case study indicates the need for a major transformation of teacher development as teachers scale the organizational hierarchy to take on administrative roles. School leaders should act as resource providers to empower the entrepreneurial behaviors of other teachers and students. This requirement represents a turning point in teacher development, as earlier stages of TEB involve resource acquisition for self-empowerment.