This study explored the role realization journey of 11 English Teaching Assistants (ETAs) in Hong Kong. Their journey is framed through the lenses of Shulman’s (1987) teaching elements of content pedagogical knowledge, knowledge of learners and their characteristics, and knowledge of educational contexts. Data from four different inquiry methods were analyzed and triangulated to map out the journey of the ETAs. During this journey, the ETAs were faced with demands for content knowledge and teaching whilst encountering educational and cultural differences in terms of students’ learning styles and working environment. The ETAs perceived these experiences as shaping their role as supportive teachers, but hoped for structured professional development to enhance their preparedness and credibility – an implication for teaching assistant training. Fundamentally, the ETAs’ readiness to embrace their role as teaching assistants through the many faces of culture, experiences and challenges surmounts their journey to understand the world of teaching. Copyright © 2011 EERA.