In artworks such as paper-cutting, it is important to combine the skill of the artist with the di culty of the rough sketch to improve the skill. We developed a system to measure the distances and widths of cutting lines and patterning the pictures based on the steering law. We quantitatively evaluated the di culty level of the pictures. We developed an interactive system to support the improvement of cutting pressure control, which is one of the skills for making paper-cutting. Furthermore, we analyzed users' psychological state when making a paper cutting based on the psychological ow state. The ow state is a highly focused state that tends to be shown when the user's skills balance with the di culty of the task. On the other hand, since it is di cult to analyze skills and di culty quantitatively, many researchers evaluate them by qualitative analysis. In this paper, we set "skill" as the cutting ability and "challenge" as the di culty level of the picture. We evaluated the improvement of the user's skill and the ow state through quantitative analysis. We developed a questionnaire to evaluate the psychological state of a paper-cutting process based on the existing ow state questionnaire. In this paper, we describe the changes in skill improvement due to the combination of user skill and picture di culty, with "skill" being the cutting ability and "challenge" being the di culty of the picture. CCS Concepts: • Human-centered computing → Pointing devices; User models.