Abstract Persistent employment failure cannot be adequately explained by job shortages, individual skill deficits, or firm-level hiring conditions. Despite repeated policy reforms, platform innovation, and resource investment, employment instability continues to reproduce itself in structurally similar forms. This persistence signals a limitation not of execution, but of definition. This paper defines employment failure as the outcome of a structural framework that treats employment as a discrete event rather than as an operational process. It identifies the Post-Matching Void—the phase following initial job matching in which employment continuity is not institutionally governed—as the primary locus of recurrent failure. Within this void, responsibility is systematically transferred away from institutions and absorbed by individuals, allowing failure to accumulate without correction. By reframing employment as an operational system requiring sustained management, this paper establishes a diagnostic framework for understanding why employment systems fail repeatedly across contexts. While the necessity of operational intervention is made explicit, the identification of intervention actors, timing, and responsibility allocation is intentionally left unresolved. This work positions problem definition as the critical bottleneck in contemporary employment systems and provides a structural reference point for subsequent operational frameworks.