This reflective journal critically evaluates work performance, skills, and organizational theory within a work-based context. The author reflects on their role as a deputy head teacher, outlining a career progression plan to own and manage a language school. A skills audit identifies strengths in education administration, project management, and communication, alongside weaknesses in time management and decision-making. The journal includes a SWOT analysis, target setting, and a skills matrix for improvement. Self-appraisal and action planning are used to enhance employability skills, and the author reflects on how skills development impacts confidence and future performance. The analysis also integrates principles of organizational theory against organizational practice, considering the author's contribution to organizational objectives.