This article presents findings from a case study that explored creative persistence through a reconceptualization of what it means to "fail" within an educational setting. Participants included in-service teachers enrolled in a semester-long graduate level educational technology course who reflected that they were able to view their failures as invaluable learning opportunities with implications for their own creativity and their professional practice. This reconceptualization is presented through examples that include a) failure as opportunity for deeper learning, b) failure as serendipitous, and c) failure as practice makes progress. A discussion of the findings further contextualizes implications for how both teachers and teacher educators can explore this reconceptualization of failure through the construction of learning environments that promote creative persistence and concludes with suggestions for how to address pedagogical issues of practical facilitation of this type of learning process within a K-12 classroom environment.