What is it that academic administrators like department heads, chairs, deans, and provosts actually do? And why would anyone want these jobs? Leading an academic unit can be challenging, frustrating, and difficult. Yet successful leadership can be deeply rewarding if you want to make a difference in the lives of your fellow faculty and students, leave things better than you found them, grow as a professional, and give back to your institution. This roundtable will explore the ups and downs of academic leadership roles so that perhaps you too may someday want to join the "Dark Side."