When school leaders make calculated decisions to deviate from hierarchical or cultural directives and norms, they may be viewed as mavericks or brigands. This paper details a process of ethical checking to help differentiate ethical decisions from more arbitrary or self-serving decisions. The paper examines conflicts inherent in many professional codes. We use our model of artistic insubordination (Buskey & Pitts, 2009) as a departure point and examine the relationship between language and steps from Dr. Martin Luther King's direct action model with concepts already found in educational leadership. We use both to develop a process of ethical checking. The process should help school leaders attempting to balance the demands of being administrative leaders, democratic citizens, and human beings (Starratt, 2004).