This chapter examines the economic inequality in higher education using Heifetz, Grashow, and Linsky's concepts of technical versus adaptive leadership. Circular problems abound in many higher education institutions today as they struggle to make up for budget shortfalls caused by reduced state and federal funding. Media frames of the wealthy are important to consider because they contribute to whether people see economic inequality resulting from individual circumstances or larger structural conditions in our society. Despite its necessity in addressing complex challenges like economic inequality in higher education, people resist adaptive leadership for several reasons. Leadership premised on quick-fix, technical solutions to socioeconomic inequality will continue to feed the cycle of inequality. Interrupting the cycle of class inequality requires leadership practices that bring about lasting improvements. Real change will be spearheaded by leaders who can embrace the importance of existing in relation to others.