In this study, an online survey was utilized to investigate relationships among participants’ willingness to cheat in academic or business settings and the strategies they tend to utilize in video game play. 113 participants completed the survey, and 86 students (23 middle school, 44 high school, 8 college undergraduate, and 11 graduate) yielded complete data. Participants were located throughout the United States, with the majority located in the Midwest and Mid-Atlantic states. The survey asked about participants’ strategies and preferences in video game play, as well as their problem-solving strategies for homework and business scenarios. Categorical principal components analysis revealed factors that predict an individual will be more likely to cheat in academics or business. Those who were willing to cheat in school or the workplace tended to use similar problem-solving strategies in those two contexts, as well as in video game play. These were strategies to make problem-solving easier, and to bypass difficult tasks instead of working through them, as well as being more likely to give up when a task was difficult. This suggests that cheating behavior may be a pervasive approach that is more highly related to personality or habits than to any influence from video game play, though the strategies used in video games are reflective of the strategies used in other contexts.