Three counterbalancing realities confront the contemporary school principal and each one has the capacity to produce psychic highs and lows in the conduct and vision of principals as they lead schools to higher levels of instructional improvement and community engagement. First, contemporary principals are expected to provide an organizational vision that will serve, promote, and advance the agendas of multiple constituencies. Second, previous personal and professional relationships are altered when individuals assume the role of the principal. And third, the work and role of the principal is invariably a lonely enterprise. In far too many principalships, a failure to acknowledge and balance these dissonant realities can result in a type of "leadership blues" that has serious consequences for productive, meaningful, and stable leadership. "Leadership blues" are personified in principals who feel overwhelmed by the complexity of the work and tasks they have been asked to perform. However, leadership education and professional development programs can assist aspiring and practicing principals to use "leadership blues" as a frame for improvement. The author argues that "leadership blues" should be viewed as a natural occurrence which, if recognized and handled appropriately, can be used to help principals counter "unrealistic expectations about their jobs, their associates, and themselves." Understanding and coping with the "leadership blues" provides an opportunity for school leaders to constantly reassess their own learning in the pursuit of leading others to success and excellence.