Project management (PM) work readiness requires preparation beyond the knowledge of concepts and best practices to develop and practice soft skills needed for successful project management. This article proposes a methodology that combines real-world practitioner tools, PM processes, and a Microsoft Excel-based PM Simulator to create a "messy" project environment for students to apply concepts supported by soft skill practice. This methodology addresses a gap in classroom strategies focusing on soft skill development via practice rather than knowledge conveyance for PM education. Faculty provides a project case study for students to plan and execute, starting with charter development and carrying through project execution. This article illustrates one potential case study, but any project planning case study can be used with the PM Simulator as long as the project plan from the case has fewer than 100 individual tasks (PM Simulator constraint). Faculty can control complexity to prevent unwinnable and overly easy scenarios preventing students from becoming frustrated or bored, each a potential learning roadblock. The simulation of an unpredictable project environment occurs as students are faced with challenges that they must assess and overcome. Two pilot implementations successfully demonstrated that students learned to create incremental project artifacts such as charters, project plans, status reports, and learned schedule versus budget-balancing concepts.