This paper develops normative approaches for measuring individual-level income insecurity. Using concepts derived from Expected Utility Theory and Prospect Theory, we build a suite of measures designed to capture various facets of psychologically distressing income risk. We present an application for the US and Germany from 1993–2013, employing conditionally heteroskedastic fixed-effects models to generate predictive densities for future incomes. Our results reveal much higher levels of income risk in the US relative to Germany, which can be mostly attributed to a higher level of autonomous, time-invariant volatility. State-by-state variations in liberal/conservative political administrations partially explain our results, and we find some evidence that trade exposure is a contributing factor in the US.