Because of their mobility and capability to adapt, self-initiated expatriates (SIEs) are very attractive for transnational companies, which increasingly view international business skills development and foreign work experience as part of career progression. SIEs are highly skilled professionals who decide to expatriate independently of any employer and mostly without organisational assistance. However, SIEs' lack of organisational embeddedness poses some challenges for companies, which need to understand how they can keep valuable resources inside the organisation. More needs to be known about the factors influencing SIEs, and about the motivations, which could help companies in attracting them in the long-term. This paper aims at exploring the impact of previous international experience of SIEs, and understanding more about the individual cultural values affecting their decisions.