Environmental, cultural, and social issues are becoming increasingly complex, and the educational context is no exception to this trend. The relevance of teachers’ creativity in examining situations from different angles, in imagining new approaches, in adapting to the varied needs of students, and in training them so that they too can grasp the teeming complexity seems obvious. However, creativity sometimes seems to be taken for granted among teachers and educational programs leave a gap around this theme. Since the scientific literature tends to show that teachers’ creativity is still little explored in educational contexts, this doctoral research studies its manifestations within a group of teachers enrolled in a professional master’s program in preschool and elementary education (Université de Sherbrooke, Canada). Within the framework of this program, each one elaborates a professional development project over a three-year period. Using a variety of authentic data sources (observations in natural occurring situations, reflective writing by participants, and semi-structured interviews), their creative process is documented and analyzed. This multiple-case study (n = 9) that draws on the concept of creativity as related to that of professional coherence reveals that the pursuit of greater professional coherence not only enables the implementation of creative skills to foster teachers’ professional development, but also elicits beautiful risk-taking.