Students often look to the standard algorithm, which requires rewriting the task, regrouping tens to create enough ones to subtract, and other opportunities to make errors. However, when the authors apply structural thinking, the resultant strategy is an efficient and elegant shortcut and even brings a positive connotation to the word "shortcut!" So, the question is, how do teachers reduce students' knee-jerk reactions to follow procedures and algorithms and increase their capacity to pause and notice mathematical structure to find shortcuts? One response is to develop their capacity to think structurally. In this article, the authors will explore what it means to think structurally and introduce an instructional routine, Contemplate Then Calculate, to engage students in and develop structural thinking so that teachers can implement it with their students.