As more organizations transition from traditional document-centric systems engineering to a model-based approach, many are challenged to train their staff in new languages, tools, and methodologies, while managing the expectations of stakeholders and their expected model outcomes. In particular, challenges associated with learning a new modeling language and developing skills in the 'art' of modeling present organizations with formidable obstacles to realizing this transition. This paper hypothesizes that systems engineers may more readily learn how to correctly model with SysML, and develop intuition about the art of modeling and using patterns, if their learning references a commonly and thoroughly-understood subject, such as a board game. This paper presents a case for the use of board games as subject matter for new modelers. It demonstrates the concept with a sample model of Hasbro's popular board game, Monopoly, and discusses the limitations of this approach and potential adaptations that may broaden the applicability of the learned skills to projects. Finally, results from a small feasibility assessment and concepts for more formal study to evaluate the hypothesis are presented.