UK continuing education is moving from credit-earning, taught continuing medical education (CME) to a continuing professional development (CPD) system that explicitly links education to change in practice, managed and monitored through mandatory peer appraisal. Alongside multisource feedback and consideration of issues of poor performance, satisfactory personal development planning will be required for relicensure and recertification. That system gives self-assessment, in the guise of reflection, a central place in personal development. This article uses instances of directed self-assessment drawn from undergraduate and early postgraduate medical education to consider how a positive system of self-assessment and professional self-regulation could be operationalized. It explores why medical students made avid use of an e-technology that presents the intended outcomes of their problem-based curriculum in a way that helps them seek out appropriate clinical opportunities and identify what they learned from them. It contrasts the experience of early postgraduate learners who, presented with a similar e-technology, found it hard to see links between their official curriculum and their day-by-day learning experiences, at least partly because the intended outcomes it offered were remote from what they were actually learning. Any extrapolation to CPD must be very tentative, but I advocate continued exploration of how best to use e-technology to support and structure (ie, direct) self-assessment. Direction could originate from consensus statements and other well-defined external standards when learners lack mastery of a domain. When learners must respond to institutional demands, direction could be provided by corporate goals. In areas of mastery, I propose learners themselves should define personal standards. In areas of difficulty, external assessment would take the place of self-assessment.