Migrants' workplace experiences in their host society, including failure, shape their social adjustment, yet "how" migrants learn from failures is under-investigated. The study presented here examined how North Korean migrants struggling for a foothold in South Korea sought to learn from failures in their workplaces and everyday life. The article draws on nine months of ethnographic research in South Korean restaurants and cafés employing North Korean migrants. Data sources include informal conversations and loosely structured interviews with five purposefully selected women who started, or planned to start, their own enterprise. The findings reveal that these migrants perceived failure in five interrelated spheres: financial, relational, physical, psychological and professional. Participants developed perspectives to understand failure as an integral part of learning in a new society and adopting unfamiliar role expectations and responsibilities. They also applied knowledge they had acquired through their failures to change their approach to their career and to strengthen their personal and business capacity to obtain a legitimate social position. Paradoxically, failures that were beyond their control, such as legal problems, created opportunities to receive practical support from, and increase trust in, South Koreans. In addition to challenging the discourse that portrays North Korean migrants as deficient, these findings contribute to adult education scholarship on migrants' situated learning in their host societies.