The COVID-19 pandemic has accelerated the adoption of telework, fundamentally altering work environments worldwide. This paper explores the impact of telework on subjective well-being, work-life balance, job satisfaction, job performance, and knowledge management among aging workers in Japan and the United States. Given demographic shifts and the increasing presence of older employees in the workforce, understanding how remote work affects this population is essential. Drawing upon cultural, psychological, and knowledge management theories, this conceptual paper develops a set of propositions regarding the interplay between telework and key workplace outcomes. We argue that cultural differences, digital literacy, and telecommuter self-efficacy significantly shape telework adaptation for older employees. Our propositions highlight variations in work-life balance, job satisfaction, and the effectiveness of knowledge-sharing practices, particularly regarding tacit vs. explicit knowledge transfer in different cultural settings. Furthermore, the study emphasizes the role of organizational support, digital training, and hybrid work models in mitigating telework challenges. These propositions provide a foundation for future empirical research to refine telework policies and enhance the experiences of aging workers in remote environments.