This study conducts an analysis about the impact of basic background, cultural capital, skill use, and participation in training on employees' problem-solving proficiency in Japan and Korea based on data from the Programme for the International Assessment of Adult Competencies Survey (PIAAC). This research compared four clusters (basic background, cultural capital, participation in training, skill usage) to determine the factors affecting problem-solving skills in technology-rich environments (PSTRE) in Japan and Korea. In addition, we examined whether aging moderate the relationship between skill usage and participation in training and PSTRE. The finding shows that PSTRE is associated with the basic background, cultural capital, and skill usage. Moreover, the interaction effect between the use of skill at home and age is statistically significant in Japan. Our results provide new insights for vocational psychology and work-life research in the context of employers, employees, as well as policymakers.