This article describes some of the benefits derived from encouraging math drawing in a class of seventh-and eighth-grade students in line with promoting mathematical proficiency. The authors report teaching pictorial representations as part of the solution process, where both students and teachers gained insight into various areas of understanding. Talking about these representations with peers helped strengthen students' reasoning and understanding. Providing problems that required students to use representations and discussion to develop reasoning skills helped students connect the logic of their thinking with mathematical concepts. In essence, pictorial representations helped students model, analyze, make sense of, and understand the underlying math within a problem. Specifically, using various types of models--area, length, and set--and discussing their usefulness in different contexts helped students develop deeper mathematical understandings. All of these habits of mind and skills take time and multiple experiences to properly learn and develop. The authors conclude that, while pictures may not be proofs, they can help adolescents create and communicate sound reasoning that can lead to proof.