This chapter explores the notion of “new teacher”, and hiring practices associated with being a new teacher in Ontario. I consider growing teaching arrangements, such as non-permanent positions like substitute teachers, to be a form of contingent work in education. In particular, I examine the nature of this non-standard work arrangement in relation to the teaching practices utilized and experiences encountered within an inconsistent work context. Data presented in this article originated from a qualitative study of Ontario, Canada substitute teachers. Findings demonstrated that several elements of substitutes’ teaching were characteristically different from permanent teaching, including: 1) daily preparation, 2) rapport with students, 3) classroom management, 4) lesson content, and (5) teaching strategy implementation. The contingent quality of non-permanent teaching has implications for how we might better develop and deliver professional learning for newly hired teachers. The chapter ends with suggestions for how to provide more appropriate professional learning and supports for new teachers.