Self-direction is increasingly becoming incorporated into the learning designs of continuing education curricula. However, it is frequently assumed that self-directed learning is intuitive. Learning a new discipline or professional practice requires the learner to transition into new ways of thinking and acting within a specific domain of knowledge. Learning new disciplinary knowledge is not simply a cognitive experience and this process is not age-specific. This paper will frame self-directed learning as a technology of the self by drawing on receptions of Michel Foucault (1926-1984), in adult education research literature, for critically understanding the social construction of subjectivity. The paper will argue that educators need to model self-directed learning for students transitioning into higher education. Through curriculum design, self-direction needs to be aligned with dispositions implicit in professional and disciplinary programmes offered by continuing education institutions. The paper will draw upon practitioner-based enquiry in continuing education at University College Cork to propose strategies where a technology of the self can be authentically assessed through formative and summative assessment techniques.