Professional practice evolves as individuals reflect and theorise about their experiences, and consider their practice in new ways. The purpose of this paper is to demonstrate how self-study can be used as an approach to interrogate the professional practice of a university advisor as they coach undergraduate students to develop meaningful resumes and job applications. Not only are the artefacts reconsidered but there is also a concurrent shift in identity and vocational persona. This paper uses the qualitative method of self-study where a practitioner provides vignettes and reflective writing to describe moments of transformative learning. These two sources of data were then evaluated using LaBoskey's five characteristics of self-study. This research highlights how self-study supports a praxis and change in professional practice. The university advisor and undergraduate students when given the opportunity to consider their practices by looking to their motivations and assumptions it is possible to precipitate transformative learning. Self-study is an approach to an epistemology of practice that is rarely used outside the education field. However, it is an approach that has significant potential for investigating the practices in arrange of professional contexts where a praxial interrogation of the work is valued.