The COVID-19 pandemic triggered a sudden shift toward remote and hybrid work, placing IT technologies at the forefront of organizational practices and revealing a spectrum of emotional responses among employees. While conventional wisdom suggests that high salaries in the IT industry safeguard well-being, this study challenges the notion that “money cannot buy happiness” by demonstrating that technostress, social isolation, and “Zoom fatigue” persist regardless of income level. Drawing on a longitudinal dataset collected at three one-year intervals, the research employs fuzzy semantics to translate qualitative survey data into quantitative descriptors, basket analysis to identify consistent behavioral patterns, and a Minimal Spanning Tree-based isolation forest enhanced by Takagi–Sugeno fuzzy rules to detect anomalies. The findings indicate a nuanced interplay of negative and positive emotions, with fear, anxiety, and fatigue frequently coexisting alongside pride, energy, and satisfaction. Some anomalies in responses reveal issues, such as random guessing or minimal IT usage, underscoring the importance of filtering out low-quality data. Crucially, the emotional outcomes are influenced not only by pandemic-related disruption but also by psychosocial and organizational factors—such as role complexity, skill requirements, and managerial support—providing a holistic view of how and why IT-based work can foster both strain and fulfillment. These insights hold practical implications for employers, suggesting that comprehensive well-being strategies, rather than monetary incentives alone, are pivotal in promoting a healthier, more resilient IT workforce.