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There is a growing national demand for information technology (IT) professionals, yet a shortage of qualified high school IT teachers. Grounded in constructivism theory and self-determination theory (SDT), this convergent mixed-methods study aims to determine the alignment between experiences and motivations of individuals when becoming high school IT teachers and to identify factors that influenced their career choice. Data from participants (n = 46) were analyzed using descriptive statistics, thematic analysis, and learning experience network analysis. The results indicated that there was no single mold for a high school IT teacher because each individual brought a unique perspective to their journey, which was influenced by personal values, professional goals, and the demands of their teaching context.