Resilience researchers from diverse disciplines and cultural settings face formidable challenges in conceptualizing and developing standardized metrics of resilience that are representative of adolescent and young adult experiences across cultures. We discuss these issues using the case example of a pilot study involving researchers in 14 sites in 11 countries. The goal of the International Resilience Project was to develop a culturally and contextually relevant measure of youth resilience, the Child and Youth Resilience Measure (CYRM). Cultural sensitivity and an iterative research design introduced to the study a number of problems that future studies of resilience will need to address: ambiguity in the definition of positive outcomes; a lack of predictability of models across cultures; and measurement design challenges.