Widely recognized for his distinguished scholarly contributions in cultural psychology throughout a career spanning more than a half-century, Jerome “Jerry” Bruner has profoundly influenced generations of scholars though his pioneering research on perception and cognitive processes. Although perhaps less widely known for another set of skills—as a sailor, Bruner remains at the proverbial helm as he charts a new course in his current position as Research Professor of Psychology and Senior Research Fellow in Law at New York University. Having authored several best-selling books throughout his extensive publishing career, Bruner continues to examine the importance of storytelling as a process of construction in education and the law in his most recent works. His conceptualization of self-narrative as the construction of a longitudinal version of self through storytelling can be aptly applied to contemporary issues in educational policy. In this chapter, the authors discuss the influence of self-narrative as defined by Bruner in their own research, specifically to better understand the use of storytelling by practitioners to construct their own identities as participants in teacher evaluation systems. The authors’ use of narrative as a framework for understanding how teachers use storytelling in context exemplifies Bruner’s profound influence on emergent pragmatic issues of policy to practice. As a visionary in the academy, Bruner’s own story can serve as a guide in uncharted waters for the next generation of researchers and scholars.