The transition from the teacher education institution to life in a real classroom has been characterized as a type of reality shock in which beginning teachers realize that the ideals they formed while training may not be appropriate for the realism they are faced with during their first year of teaching. Unfortunately, teacher education programs have not had a successful history of adequately preparing beginning teachers for this transition because learning to teach is often viewed as being a highly situated, highly interpretative, and idiosyncratic activity. This paper suggests that the use of a "story structure" framework ("setting-complication-resolution") may be one method of imposing some order on the various descriptions of first-year teaching experiences. The paper reports on a case study of how a first-year English language teacher experienced the transition from a teacher education program to life in a real classroom, and how he balanced a delicate, and sometimes conflicting, role between learning to teach and learning to become a teacher within an established school culture in a neighborhood secondary school in Singapore. Three major challenging situations are identified and the teacher's responses with each as he struggled to establish himself as a teacher.