The Dominican community in New York City is a clear example of a transnational community: migrants move between the Dominican Republic and the United States, maintaining strong ties with both places. Dominicans migrate because of economic difficulties and to rejoin family members who have gone before them. Families often move in a stepwise fashion, with one or two members of the household immigrating first, and then bringing others over. Here we discuss the oral histories of three immigrants, Manuel, Yngrid, and Maria, who were separated from their families for at least three years during the course of immigration. Each decided to move to the United States, sometimes against the will of their family members. They were motivated to immigrate to escape difficult financial situations, to seek new opportunities, and to provide for family members who were left behind. In varying degrees, these narrators felt that they had no other option but to go to the United States. Manuel fulfilled the traditional patriarchal role of decision-maker and financial supporter of the family, while Yngrid and Maria both went against traditional gender roles, taking on the role of breadwinner and redefining it in terms of the traditional caregiving role.