For decades, Singapore’s professional class operated under a relatively stable social contract. Study hard. Enter a strong industry. Climb steadily. Accumulate assets slowly. Retire comfortably. That model is now being stress-tested by artificial intelligence. Not because AI is suddenly replacing everyone overnight. But because it is beginning to fundamentally change the economics of white-collar work. And perhaps for the first time in years, many Singapore professionals are starting to realize something uncomfortable: high income does not necessarily mean high career security. Recent labour market data in Singapore reflects this shift. Total retrenchments in 2025 rose to approximately 14,400–14,500 workers, up from around 13,000 in 2024. Financial services and technology-related sectors were among the most affected. At the same time, business restructuring now accounts for roughly 60–70% of retrenchments according to MOM. Importantly, restructuring increasingly includes productivity improvements from AI and automation adoption. This distinction matters. Historically, layoffs were often cyclical. Companies retrenched because demand collapsed during recessions. But increasingly, modern retrenchments are structural....