This article provides a look at both how design-thinking behaviors may be taught and encouraged in students and potentially provides a look into the Matthew Effect in education/achievement gap. It does this by providing students with choice-based assessments (CBA) which are meant to test how students address challenges through learning without being given guidance. Students must know how to deal with said challenge but be able and willing to use higher-thinking strategies without prompting. In order for this to occur, the study instilled design-thinking strategies meant for students to be able to think critically about problems and solve them on their own.