Reflection is a key component of the transformative learning process. In this study, we take steps to define components of reflection and link them to a computer-based, quantitative method of content analysis called Linguistic Inquiry and Word Count (LIWC). This method can be used to evaluate common forms of reflective writing such as journals, reflective essays, and blog posts. It has several advantages over more common qualitative approaches for measuring reflection. We test the efficacy of this quantitative measurement approach with data from 98 study abroad university students. The results indicate strong explanatory power that tracks well with theory and observation of the reflective process. Our approach follows procedures for construct validation of the measurement method. As an early step to use quantitative methods with reflection, the LIWC shows promise. However, much more research must be done to extend these initial findings both in measurement and theory development.