This chapter investigates the constraints impact on the creativity of millennial preservice teachers when captioning a New Yorker Magazine cartoon. According to research, millennials have a decreased capacity for unique ideas, synthesis, articulation, and open-mindedness, which limits their ability to function in a diverse world. The study examined the topic using the constraint-based model of novelty (C-BMN; creativity problem, constraints, variability, and problem spaces) as a framework, as well as the new rubric, which assessed data on the impact of constraints on creativity among 90 millennial PST. Inferential statistics were used to compare differences in creativity, and the results indicated a statistically significant difference in total caption creativity between the experimental and control groups. The study corroborated previous research, concluding that constraints foster creativity. The findings of this study have implications for stakeholders interested in incorporating constraint-based strategies to increase cognitive diversity.