Much of the literature in library leadership and management focuses on strategies and practices based on discrete attributes and sweeping human behaviors intended to improve operational effectiveness. This paper challenges the reader to build a mindset for leadership that reflects the real world, where leaders and managers work within parameters often contradictory and at times unconventional. It acknowledges the complexities of leadership in terms of decision-making and judgment within the culture of the organization rather than standard characteristics seen as desirable in a leader. The distinction between leadership and management is also examined.