In Sri Lanka Army soldiers retire in the active age group of 40-45 and most of them are with lots of experience, skills, knowledge and potentials which could be utilized to enhance the country's economy whilst providing them with meaningful employment opportunities or converting them as successful entrepreneurs. However, there is no realistic and scientifically drawn up mechanism in Sri Lanka to properly absorb them into the active labour force with maximum utilization. In this backdrop, their skills, knowledge and potentials will be underutilized and it will be a loss for the country's economy in the long-run. Unlike in developed countries, in Sri Lanka, this issue of veterans' transition into successful civilian life has not yet been addressed by both researchers and policy makers. Moreover, many researches undertaken by defence establishments rarely come into public domain. This study examines the entrepreneurial aspirations and the expectations of retired military personnel of the Sri Lanka Army in successful transition from military life to civilian life and preparing them for entrepreneurship as a post military career choice.