Secondary principals serve in important roles that are complex, high-stress, and include demanding job responsibilities. Key stakeholders such as superintendents, school board members, and legislators must understand the challenges facing secondary principals in order to address the current themes of job dissatisfaction. Using new survey data compiled from 176 secondary principals across a state in the Midwest United States, this study shows four themes of job dissatisfaction are plaguing secondary principals: high job demands with unreasonable expectations, managing difficult stakeholders, problematic work/life balance, and lack of support. This study concludes with practical suggestions to address each theme of job dissatisfaction.