Issues of school autonomy and principal autonomy has been given much attention in education policy and politics in Australia. School autonomy agendas in England and the United States in the form of academies, free and charter schools have been observed with interest by Australian policy-makers and educators. By understanding the nature of changing subjectivities of school principals undertaken through the neoliberal rationalities of government, it can become possible to identify ways that school principals are constrained. The chapter highlights the importance of the construction of a form of subjectivity that, as a part of these neoliberal rationalities, is important for understanding the shifting nature of the school principal as a particular type of subject, an entrepreneurial subject. Principals must work to maximise outcomes for their clients, that is, in terms of students’ performance on standardised tests. Schools must compete for clients and manifestations of choice and competition are bound up in the MySchool website.