This study explores how the various stakeholders of a teacher residency program define what it means for a teacher resident to be successful during the residency year. Researchers employed a qualitative case study design and conducted interviews with the university faculty, residency program staff, mentor teachers, and graduates of the residency program in order to conceptualize teacher resident success. The findings that emerged emphasized developing an understanding of learning from failure. Second, the arc of a full year of pre-service training gave program participants the opportunity to learn how to effectively establish relationships, develop a teacher presence, and maintain work-life balance. These findings serve as a reminder of the human and interpersonal nature of teaching and learning, and that success is more than some numerical measure of effectiveness. The paper concludes with a call to better inform residency program planning and evaluative documents that can help residents grow based on a qualitatively operationalized definition of success.