This case study focuses on emotionally draining situations for school leaders in the context of work intensification. Specifically, this study draws upon real-life reports from Canadian studies to present a fictitious scenario. This case depicts a high school principal who must simultaneously deal with student discipline, interact with parents, conduct classroom walk-throughs, complete tasks associated with being an instructional leader, and work with teachers—to name a few. Readers are encouraged to connect research to practice through several teaching activities that include: a jigsaw discussion approach, a think-pair-share approach, a forum theatre approach, and a pro and con grid approach.