This article provides insights into the challenges facing US public school principals. A survey was sent to a random sample of over 10,000 principals throughout the US. Written responses from a representative sample were analyzed for content and themes. Results indicate that principals are facing emerging challenges never before seen in education, including the overwhelming effects of poverty, increasing pressures on student achievement, the breakdown of communities, lack of financial resources, and a host of other issues, many of which coalesce to further complicate the work of principals. The voices of these principals suggest a need to radically rethink our preparation programs for school administrators.