How do high school students approach academic and creative challenges? This study compares the content of academic and creative challenges for 190 high school students, and examines students' intentions to persist. Students reported experiencing academic and creative challenges in different areas: academic challenges were described primarily in math/science and English, with themes related to time management and striving to improve, while creative challenges were described overwhelmingly in art and music and concerned problem solving difficulties. Students reported more interest and intention to persist in the creative than academic challenges. Interest was the strongest predictor of persistence across both academic and creative challenges. The divergent perceptions of creative and academic challenges suggest that capitalizing on the creative elements of academic assignments could boost student interest and subsequent persistence.