This paper provides empirical and contextual insight into the complexity of Self-Initiated Expatriates’ (SIEs) experiences in a unique setting. Factors that influence SIEs in the civil engineering industry, when considering overseas employment in Qatar, are identified and considered. Drawing comparison to organizational expatriates (OEs), this paper uses semi-structured interviews conducted with professionals from the civil engineering and construction industries. The research surfaced that different factors interconnect to affect individuals’ decisions about overseas employment. Three factors, specifically; location appeal, host country as an employment setting and effect of expatriation on the family, appear to be more influential to participants when the proposed destination is Qatar.