With state content standards always looming in the background, history teachers express concern about "covering the curriculum." And, many history teachers say they have to abandon teaching the "fun stuff" in order to teach state-mandated content. While teaching challenges do entail practical considerations, this article argues that teachers gain insight into planning effective instruction if they view the challenges they face as fundamentally intellectual, involving conceptual knowledge and historiography. The author suggests that history teachers face three particular intellectual challenges they need to manage which rest at the core of historical understanding. These challenges involve issues of time (the past and the present), scale (the large-scale and the small-scale), and pattern (the unique and the more common). Teaching with these issues in mind offers a challenge because both poles of these three issues have legitimacy and deserve consideration. In all these cases, the author explains why each pole deserves a history teacher's attention; he presents a question to ask in deciding how to balance the competing demands of each pole; and then he offers a brief example of one way to implement instruction that attempts to honor both poles. For the sake of thematic consistency, all three examples are drawn from antebellum United States history. (Contains 20 notes.)