This article examines the relationship between confidence and risk in relation to the initial education and continuing professional development (CPD) of teachers. The context for this examination is the Lifelong Learning Sector (LLS) in England, which sits between secondary schools and universities, and the discussion is illustrated with data gathered from trainee teachers in this sector. Understandings of confidence are considered and it is argued that the inculcation of confidence through risk-taking is important for new teachers in their journey to praxis. The article concludes by arguing that the transformative potential of critical engagement with professional knowledge on teacher education courses and through work-based learning (WBL) should be balanced with the need for the good and appropriate time necessary for the risky political act of reflection, not merely the immediate technical evaluation of practice.