This article discusses the concept of Old Boys, a term used to refer to alumni of a particular school or organization in Japan. It covers the history of OBs in Japan, different types of OBs, benefits and challenges associated with being an OB, how to become an OB in Japan, and advice from Charles R Tokoyama, CEO of Japan Insiders. It is possible for individuals to join an Old Boys network and benefit from job opportunities, networking contacts, professional development activities, and mentorship programs. However it requires dedication and commitment as staying connected with current students/alumni helps keep skills sharp and up-to-date.