Developing confidence in self-assessment is an important skill in becoming a self-regulated learner. This article describes the process undertaken by a group of educators of incorporating self-assessment in combination with psychomotor skill development with freshman students. Students were videotaped performing a wound-dressing change; the videotaping was immediately followed by a self-assessment of their performance using a faculty-generated checklist. Comparison of faculty and student ratings revealed the tendency for students to overrate their performance and identified discordance between students and faculty on several steps of the procedure. These evaluation findings are discussed and future directions explored.