The term failure typically evokes negative connotations in educational settings and is likely to be accompanied by negative emotional states, low sense of confidence, and lack of persistence. These negative emotional and behavioral states may factor into an individual not pursuing a degree or career in science, technology, engineering, or mathematics (STEM). This is of particular concern considering the low number of women and underrepresented minorities pursing and working in a STEM field. Utilizing interview data with professionals across STEM, we sought to understand the role failure played in the persistence of individuals who enter and pursue paths toward STEM-related careers. Findings highlighted how participants' experiences with failure (1) shaped their outlooks or views of failure, (2) shaped their trajectories within STEM, and (3) provided them with additional skills or qualities. A few differences based on participants' sex, field, and highest degree also manifested in our analysis. We expect the results from this study to add research-based results to the current conversation around whether experiences with failure should be part of formal and informal educational settings and standards-based practices.