The relationship of an expatriate to his or her country of origin is complicated by reasons for leaving, ease of acculturation into the new country, nostalgia, loneliness and the ability to remain connected to his or her country of origin while abroad. Research on expatriate experiences has been limited to certain countries of origin and host countries, as well as a narrow definition of the term “expatriate”. The purpose of this qualitative study was to explore the experiences and relationships with host and home countries of Syrian self-initiated expatriates, an underrepresented group in the literature. Phenomenological interviews were conducted with 13 Syrian self-initiated expatriates during an expatriate conference in Damascus, Syria. The results showed that Syrian self-initiated expatriates have left Syria to advance their education and their careers. For many of the men interviewed, Syria’s mandate of military service was a factor in leaving. When in their host countries, they faced adjustment issues such as language barriers and difficulty remaining connected to Syria. Relationships with both countries were fluid and changing, based on factors such as adjustment and ease of communication. I make recommendations for improving travel, communication and cultural maintenance to support the connection between Syrian self-initiated expatriates and Syrian society.