The generative framework of transformative learning theory (Mezirow, 1978; Taylor and Cranton, 2012) has recently found wide application in higher education ‘high impact’ learning experiences (e.g. study abroad, international service learning and practice, etc.). Scholars and practitioners, however, struggle to operationalize the theory in such a way that transformative outcomes associated with high impact learning experiences can be effectively measured and documented. This chapter discusses an on-going project to construct and pilot various methods for measuring transformative learning. To operationalize the theory, Hoggan’s (2016) taxonomy of transformative learning constructs is aligned with the 17 scales of the Beliefs, Events, and Values Inventory or BEVI (Shealy, 2016). Transformative learning theory is also operationalized qualitatively with the Valid Assessment of Learning in Undergraduate Education (VALUE) rubrics of the Association of American Colleges and Universities (Rhodes and Finley, 2013). We conclude by discussing future directions of this exploratory theoretical work and its potential applications.