A better match between formal education and work-life is seen as one approach that can help students acquire competences and knowledge necessary for successful participation in their future lives. However, emphasis is often placed on exploring practices targeted at students nearing entry into a work-life pattern, whereas promoting key competencies and positive attitudes toward work should start at an earlier stage. We conducted in-depth interviews with 20 Estonian primary school teachers, recognized by their colleagues for outstanding practices to explore their understanding and experiences of integrating work-life and students’ work-related experiences in classroom learning. While teachers involve the work-life and professions of the students’ family members, they often overlook the potential of their local community. Teachers perceived the primary school context as generally supportive, with the national curriculum and cooperative relationships with families being supportive factors. Teachers often viewed students’ work-related experiences as limited to tasks like maintaining tidiness, with few recognizing broader experiences, such as taking on different roles or participating in after-school activities. There is significant potential to purposefully connect work-life and classroom learning, enabling students to take on roles that promote their key competencies and agency, while personalizing learning based on their work-related experiences.