The current study discusses Career Management of Nigerian Army Officers and attempts to examine the importance of personal development during their service years as a necessary ingredient for proper reintegration into civilian society. A stratified sample of serving and retired officers from the rank of Captains to Major Generals was selected to determine their social and economic satisfaction in their military career. The study employs the socioeconomic (SES) model to measure the work experience based on income, education and occupation and uses Grounded Theory in its approach and analysis. The study acknowledges that personal development for the officers in form of entrepreneurship education to enhance proper reintegration into the civilian society is grossly lacking. The problem was found to be connected with the career management predicated in the history, policies and administration of the Nigerian military force. Another challenge is the lack of time and allowance for the officers to develop themselves individually while in service due to the nature of military job. The socioeconomic condition of the officers therefore changes on retirement leading to all sorts of behaviours. The study postulates a change management approach through policy reviews and robust institutional arrangement for personal development in order to provide motivation and achieve the desired satisfaction.