While teacher retention is a pressing issue for many jurisdictions, Singapore has a relatively low teacher attrition rate. Drawing on the experiences of student teachers from the sole institute for pre-service teacher education in Singapore, this article argues that it is important to expose teacher candidates to a substantial period of school experience as part of the teacher recruitment process. Before they are officially enrolled into pre-service teacher education, the Ministry of Education in Singapore requires all teacher candidates in the Postgraduate Diploma of Education program to go through a compulsory school stint. The authors' research findings show that this exposure to the realities and complexities of teaching can be an important contributor to teacher retention in terms of assessing and promoting teacher candidates' resilient qualities, such as "passion for teaching," "self-efficacy beliefs," and "positive emotion." In other words, early field experiences can help teacher candidates understand themselves as teachers and assess their own suitability for a teaching career. This study sheds new light on the policies and practices of teacher retention and teacher recruitment strategies.