This paper analyses the determinants of poverty and subjective well-being to determine whether there are differences, particularly since measurement of objective and subjective poverty may lead to different headcounts as seen in the 1999 Jamaica Survey of Living Conditions (JSLC) Report. The results suggest that while there are differences in the reasons for households classifying themselves as poor and the determinants of objectively defined poverty, there are not many differences in the underlying variables influencing the outcomes. The explanations seem to rest on households’ perception of their vulnerability, adaptive expectations, educational attainment, labour market experiences, region or area of residence, industry and sector of employment and the involvement of children and the elderly in the labour market and the sacrifices made in attaining a given level of consumption expenditure.