What do our students need to unlearn in order to consider contending perspectives, and how do we accomplish this? It is not hard to have our students supplant one orthodoxy with another, to accept a theory that we, as their professors, might find more appealing than the neoclassical one, but how do we get them to be able to think through rhetoric of all types, develop moral positions for themselves, and ultimately be comfortable with complexity and uncertainty? This essay draws from my experience teaching two ostensibly unrelated courses – introductory statistics and introductory microeconomics. I discuss the problems my students experienced in understanding theoretical frameworks and that there are contending frameworks. Drawing on the work of Perry and others, I compare the ‘what is-the-right-answer’ disposition of traditional age students with the conceptual difficulties my statistics students have in discerning the difference between uncertainty and relativism. Overlaying these somewhat generic difficulties is a problem specific to teaching contending perspectives in economics. The worldview we are asking our students to question is the one supports a world view that seems natural to them. The essay concludes with a discussion of how we might incorporate the insights of learning theory into how we teach economics from contending perspectives.