This chapter focuses on understanding cultural distance (CD) with respect to nations, organisations, and careers on an individual level and aims to contribute with nuanced conceptualization of CD for self-initiated expatriates (SIEs). The chapter begins by reviewing the literature on the notion of CD and then synthesize the extant critique to existing CD research. We derive implications for how CD could be conceptualized and measured to better include the specific characteristics of SIEs. It emphasizes implications for research and important avenues forward for an underrepresented area in SIE careers research. Most prevailing studies use a positivist paradigm to measure CD. Studies have shown that for some groups of SIEs, such as ‘explorers’ who are essentially motivated by experiences, adventure, and a new country’s culture, CD is a key positive stimulant for their mobility.