The Old Testament sages regularly taught in ways that involved ambiguity and created tension in the minds of their students. Such teaching methods were intended to stimulate thought and reflection on the part of their students as they sought to answer the questions raised by these dilemmas. These intellectual and applicational struggles played a significant role in moving students toward the goal of developing skill in living according to Yahweh's order. An understanding of this methodology may be useful in understanding a difficult book like Ecclesiastes. at the same time the use of such teaching strategies may have relevance for teaching in various educational contexts today.