Self-direction skill is considered a vital skill for twenty-first-century learners in both the learning context and physical activity context. Analysis skill for self-directed activities requires the students to analyze their own activity data for understanding their status in that activity. It is an important phase that determines whether an appropriate plan can be set or not. This research presents a framework designed to foster students' analysis skill in self-directed activities, which aims (1) to build a technology-enabled learning system allowing students to practice analyzing data from their own daily contexts, (2) to propose an approach to model student's analysis skill acquisition level and process, and (3) to provide automated support and feedback for analysis skill development tasks. The analysis module based on the proposed framework was implemented in the GOAL system which synchronized data from learners' physical and reading activities. A study was conducted with 51 undergraduate students to find reliable indicators for the model to then measure students' analysis skills. By further analyzing students' actual usage of the GOAL system, we found the actual activity levels and their preferences regarding analysis varied for the chosen contexts (learning and physical activity). The different context preference groups were almost equal, highlighting the utility of a system that integrates data from multiple contexts. Such a system can potentially respond to students' individual preferences to execute and acquire self-direction skill.