Products are often optimized for “most likely” conditions, but unexpected variations can render designs ineffective. Using examples from engineering systems, this paper explores the benefits of leveraging non-linear “payoff functions,” where small changes in conditions lead to disproportionate outcomes. By analyzing the direction and curvature of these functions near observed boundaries, designers could gain an understanding of behavior beyond expected ranges. Non-linear modeling can aid in assessing design margins, especially in long-lived systems. Integrating this approach into design processes can be helpful and effective in considering the “preparedness” of a system in the face of unexpected events of different natures.