When Mikhail Gorbachev initiated economic reforms in the mid-1980s, many people in the USSR found international peddling more profitable than anything else they could do. At first, tens of thousands of Soviet citizens poured into ‘socialist’ Poland, Hungary, or China, but by the mid-1990s the trade expanded to include thirty million people and a wide range of countries and became the backbone of Russian consumer trade. Even though scholarly works have begun to acknowledge the unique role of this shuttle business in the post-Soviet Russian economy, this study analyzes the role of gender in the business based on extensive oral history fieldwork. The research demonstrates that even though the shuttle business gave women new opportunities for financial advancement, their prolonged absence from home and the specificity of this semi-legal trade also brought high rates of divorce and rising health problems for these women as well as lack of parental control for their children. These women-traders facilitated the transition to a free market economy in Russia but their shared experiences demonstrated the gap between the rhetoric of free market economy and the actual market practices of the 1990s.