Subjective well-being, in contrast to other commonly used performance metrics such as gross domestic product, appears to offer a way to directly measure what society aims to achieve. Subjective well-being modeling to date has been restricted to regression analysis. This paper synthesizes and critiques existing literature and case studies to examine the challenges and opportunities presented by more advanced computations of well-being, including spatial, optimizing and spatial-optimizing models, which may well be created by researchers in the future if current policy level interest in well-being continues to grow. Subjective well-being is a promising measure, especially in light of recent research that shows reliable correlations with objective measures. However, the issue of individual adaptation means that excessive focus on subjective well-being may discriminate against groups with lower expectations and higher ability and/or willingness to adapt. Alternative approaches such as equivalent income may address this issue, at the expense of being harder to measure. Through an examination of four case studies and one thought experiment, we find that modeling challenges include nonlinearity, interaction, spatial sorting and extrapolation beyond valid limits. A significant research gap is found in how individual well-being scores should be aggregated to a collective one; this is a normative question although descriptive ethics would appear to offer a practical approach.