Leadership is one of the key factors for development of all organizations be they small or large. This study describes the feelings and thinking of the author on leadership aspects basing on his own practical experiences from being a University of Dodoma Academic Staff Association's Leader. The author was elected as a chairperson of the University of Dodoma Academic Staff Association (UDOMASA) in October 2010, and held the post for two terms of two years each consecutively as the constitution required. The author explains his leadership journey through different stages. The study focuses most on what it means to be a staff association or trade union leader in a higher learning institution. The study further provides details about glaring moments of comfort and upset while posing way forward for a harmonious growth for both institutions and members of the organization.