Failure, ubiquitous in life and medical practice, offers myriad opportunities for learning and growth alongside challenges to overall well-being. In this article, we explore the nature of failure, it’s sources and impacts in perioperative medicine, and the specific challenges it brings to trainee well-being. With a deeper understanding of the societal, psychological and cognitive determinants and effects of failure, we propose solutions in order to harness the opportunities inherent in failures to create brave and supportive learning environments conducive to both education and well-being.