The main purpose of this study is to identify those factors that could potentially enhance the self-esteem of Self-Initiated Expatriate (SIE) educators in Primary and Secondary education in the Sultanate of Oman and the influence of self-esteem on their job satisfaction. In a culturally different environment where people migrate generally to improve their financial conditions, this study also aims at identifying the influence of rewards, and recognition on the impact of self-esteem on job satisfaction. Data about the perceptions of Organizational Support, Support to Students, Teaching Philosophy, Self-esteem, Rewards and recognition, and Job Satisfaction of 535 self-initiated expatriate teachers of Primary and Secondary education in the Sultanate of Oman has been analysed by correlation and regression analyses. The results showed that variables like Organizational Support, Support to Students, and Teaching Philosophy were highly significant in predicting the Self-Esteem of teachers. It was also found that the relationship between self-esteem and Job Satisfaction was not moderated by Rewards and recognition. The implications of this study are of greater relevance to the School Management Committees and the School Administrations on the need to adopt appropriate strategies to enhance the self-esteem of educators.