As scholars, we are responsible for examining the academic and pedagogical traditions from which our current approaches have developed. This includes the historical establishment of and reliance upon rationality which postmodernist scholarship argues unconsciously guides our educational motives and processes. Rationality is especially relevant to transformative education, as it constitutes the theoretical basis of reflection, the very bedrock of transformational learning. However, postmodernist scholarship criticizes rationality, as it falsely assumes the existence of universal truths; reflection may in fact undermine the very purpose of transformative learning reinforcing dominant paradigms and ways of thinking. This article sets forth the limitations seen as inherent in reflective practices within transformative education and offers alternative conceptualizations of rationality to provide possible directions forward. This is specifically relevant to the subfield of transformational service learning, an increasingly popular pedagogy in higher education today.