In on-demand education, students often experience problems with directing their own learning processes. A Structured Task Evaluation and Planning Portfolio (STEPP) was designed to help students develop 3 basic self-directed learning skills: Assessing the quality of own performance, formulating learning needs, and selecting future learning tasks. A case study with 10 first-year students in the domain of hairdressing was conducted to evaluate STEPP's use, usability, and perceived effectiveness. Results from student interviews show that usability and use are influenced by several factors. Students with low prior hairdressing skills, a weakly developed personal approach to direct their own learning, and an inclination to update STEPP as part of their weekly routine, use STEPP more frequently than students without these characteristics. Both the supervisor and students who frequently used STEPP perceived its use as a positive contribution to the development of self-directed learning skills. Furthermore, this study provides guidelines for the design of development portfolios in on-demand education.