Considering the range of social justice issues at the forefront of 21st Century American life, and the ways in which these issues manifest on community college campuses, leaders must examine their responsibility to confront inequities and promote change. Transformative leadership is a style of leading that explicitly acknowledges inequities within and outside of an institution, embraces collective action, and imagines possibilities for change. In this chapter, I connect the concept of transformative leadership to the historical and contemporary legacy of activism. This connection leads me to propose inside-outside strategies as a necessary element to the practice of transformative leadership in order to meet the current sociopolitical moment.