This small-scale action research project explores the possibilities and challenges involved in facilitating a Mathematics Teacher in understanding the notion and practice of linking mathematics with students' real lives in their classroom contexts. The effort is based on the rationale that mathematics needs to be linked with real life in order to maximize the attainment of set curricular goals and objectives. However, the assumption is that in most cases the curricular goals and objectives are not satisfactorily met due to the teachers: a) limited access and understanding of curricular goals and objectives, and b) limited knowledge and expertise in effective implementation of the linking mathematics with students real lives. In this background, the project sees, linking mathematics with real life, as one of the important ways in assuring the attainment of goals and objectives of linking mathematics with students' real life experiences. To realize this aim, the action researcher worked with one secondary level secondary level mathematics teacher in a government school of Karachi, Pakistan. In this regard, the project studies the teachers existing perceptions and practice of linking mathematics with students' real lives. Subsequently, a strategic action plan was prepared and implemented to facilitate a teacher's understanding and practice of linking mathematics with real life. Subsequent planning and action remained responsive to any need for change arising out of the experiences of implementing the previous one. The data for the action process was collected through semi-structured interviews, lesson observations notes, the researcher's reflective journal and tape recordings. The gathered data was analyzed soon after each action step for reflection and further action. The study reports some possible strategies to facilitate a teacher in gaining an understanding about the notion of linking mathematics with real life. These are: 1) Using "input/training" session about "definition and theory" of linking mathematics with real life. 2) Sharing strategies for content, pedagogical and organizational linkage (i.e. mathematics with real life). For example, adding supplementary reading materials from sources other than the prescribed textbooks. At the same time and vein, the study also reports the challenges faced in the process; such as: time availability for action and its research and overemphasis on the theoretical input. The report concludes by presenting key learnings experienced as a teacher educator and an action researcher, and suggests a focus for further action research.