The first year of teaching can be intimidating and overwhelming regardless of the quality of one’s teacher preparation. Luckily, Ian had experienced several rich transitions into teaching, such as the coteaching experience and the curriculum development project, which we described in previous chapters. This chapter aims to describe Ian’s first year as a full-time teacher and bring to light some of the challenges he faced given the structural changes he encountered at an urban school that was highly distinct from City High, where he had done his student teaching. We also elucidate the ways in which Ian was able to find success during his first year of teaching by restructuring the classroom to meet his needs, by building trusting relationships with students that bridged differences and by infusing science teaching methods and activities in his math class.