This article aims to analyze the autobiographical records left by Chun Yun-hee, who came to Hawaii in 1915 as a Korean picture bride, through the lenses of gender, family, labor, and entrepreneurship. First, this article examines the motivations and causes for her transcountry mobility during Korea's Japanese colonial era and subsequent local-level relocations within the Hawaiian Islands. Second, it sheds light on her labor and economic activities in the period after her migration to the United States, particularly focusing on her involvement in Hawaii's lodging business. It examines why and how she entered and operated lodging businesses, specifically in terms of capital, labor, and customers; how gender and geographical conditions affected her entrepreneurial activities; and how she interpreted the meaning of her work. It is expected that this study will contribute to an improved understanding of not only immigrant women entrepreneurs in general but also the economic adaptation processes and the role of social networks among Korean picture brides in particular.