Sport, for as long as it has existed, has held a purpose of developing character in competitors. Positive psychology establishes that each of us has unique character strengths core to who we are that support our well-being. Athletes often develop their sense of self during adolescence and formative college years while competing at elite levels. This results in a strong “athlete identity” and a self-concept centered around sport participation, performance, and team membership. Each year, approximately 150,000 National Collegiate Athletic Association (NCAA) student-athletes graduate, very few going on to play at professional levels. Athletic retirement is a pivotal transition where redefining one’s identity beyond the role of athlete is necessary to flourish. What if identity was redefined leveraging one’s best traits? Could character strengths developed through years of athletics support effective coping through this major life transition and lead to flourishing in new life domains? This paper reviews the research on character strengths and discusses how, when cultivated through mindfulness, goal setting, and growth mindset they can help retiring student-athletes achieve greater well-being. A model for character strengths use is presented with implementation recommendations aimed at helping student-athletes attain greater well-being at the culmination of their athletic career.