In this article, the author suggests that if there is one thing that can be said about nontraditional superintendents--the men and women of business, government and the military who leave those fields to become school system leaders--it is that they never take the easy job. "School districts tend to look outside for a superintendent only when things have gotten so bad that doing the same old thing just doesn't feel like it's going to work," says Thomas Vander Ark, executive director of education and scholarship programs for the Bill and Melinda Gates Foundation and a former businessman-turned-superintendent in Federal Way, Washington, from 1994 through 1999. "That's when boards start looking at alternative sources for a new superintendent, someone who will generally come into a job embraced by all manner of unreasonable expectations." And why not?