The legal academy is increasingly focused on producing practice-ready lawyers. For transactional practice, that notion requires that attorneys have the flexibility, creativity, and business acumen to draft documents that anticipate contingencies and accomplish clients’ goals. Effective lawyers are able to structure their clients’ affairs to provide a balance of flexibility for, and protection against, the predictably unexpected. To further this goal, this article incorporates pedagogical theory to introduce a classroom exercise that focuses on creativity and contingency planning in the transactional drafting context. It does so by introducing that process in a nonlegal context, specifically by having students plan a dinner party and memorialize the arrangements in a valid contract. By developing accessible classroom exercises that incorporate everyday contingencies, law professors can hone students’ abilities to anticipate and adapt to factual and legal contingencies, and accordingly, to be effective planners and drafters as they transition to practice. Thus, this article augments the tools employed by law schools for developing this deeper concept of a practice-ready lawyer.