This paper discusses the planning processes and plans of school principals in Israel. It describes how educational planning processes often expose educators to a dilemma: public expectations pressure principals to create quick solutions for complicated educational issues, whereas their professional obligation is to produce plans that will address the complexity of these issues in an adequate and effective manner. To examine this dilemma, 163 Israeli school principals in 4 different districts were asked to define time perspectives for planning processes and plans related to 4 central policy issues in the Israeli educational agenda. The principals were also asked to prioritize future planning. The study was conducted shortly after a large influx of Ethiopian and Russian immigrants. The results indicate that the principals believed that the four issues were highly complex. However, principals tended to simplify the complexity of issues when the urgency related to these issues is high. Public education was characterized by mixed-typed situations that presented dilemmas for educators. These dilemmas exposed educators to a contradiction between their desire to meet social and political interests and their professional duty to perform planning processes that enable them to address properly the complexity of educational issues. (Contains 30 references, 3 tables, and 1 figure.) (RJM)