School leadership is an important factor in educational reform and school transformation. This article aims to examine the challenges of school leadership in Singapore through the lens of the Fourth Way. In particular, this article makes reference to three messages in the Fourth Way and examines the paradoxes and challenges faced by school leaders in Singapore associated with each message. The article argues that the government both drives and steers the education system; that democracy and professionalism, and bureaucracy and market coexist; and that educators embrace both accountability and responsibility.