The purpose of this study is to broaden theoretical meaning of challenge and attain a place for its practical use in schools. Based on the purpose, a theoretical construct was developed to explain four types of challenge-oriented behavior: (a) creators, (b) choosers, (c) maintainers and (d) avoiders. 634 fifth-, sixth- and seventh-grade students in Istanbul, Turkey, participated in the study. The Challenge-Oriented Behavior Scale and the Challenge-Performance Test were the main instruments. The Challenge-Oriented Behavior Scale scores were subjected to non-hierarchical cluster analyses, which revealed four profiles. To gain ecological validity of the current understanding, an alternative method, reverse-action strategy was developed. The aim was to explain how actual student performance is defined by self-perceived challenge-orientation type. To this respect, the Challenge-Performance Test scores and other factors were examined using path analysis. The findings suggest that demonstrated performance in pursuing challenges arise from past experience, academic achievement, self-perceived challenge-orientation type and age.