Nurturing “basic and generic skills” is important for children’s well-being. These skills encompass four critical domains: “interpersonal and social,” “self-understanding and self-management,” “problem-solving,” and “career-planning.” Collaboration between schools and communities through learning activities is crucial for cultivating children’s career-planning skills. We conducted a controlled experiment in the cities of Yotsukaido and Sakura in Chiba Prefecture. We proposed an instructional design utilizing our previously developed Cloud-Based Creative Work Sharing System called Manadasu to promote output-driven learning. This study builds upon our previous implementation, where only the LeaFeS system was utilized to support children’s reflective learning in community activities. In contrast, the present study adopts an integrated use of both LeaFeS and Manadasu. By combining task logging with creative output sharing, we aim to enhance the learning feedback cycle and deepen children’s engagement in problem-solving and career exploration.