There is growing interest in the measurement and conceptualisation of wellbeing due to its increasing importance within policy outcomes; however, the understanding of how different wellbeing outcomes associate within sustainability research is limited. This paper uses household survey data from the vulnerable Volta Delta, South Ghana, as a case study to illustrate the different philosophical approaches and measures of wellbeing, and the potential impact upon policy interventions. The frequent use of objective wellbeing measures, such as monetary poverty, within development policy is challenged as to whether it sufficiently reflects overall wellbeing. For example, objective monetary measures may not incorporate the intangible components of wellbeing, which can alternatively be captured within individuals’ self-evaluated, subjective wellbeing. This study first outlines the conceptual and methodological choices required when measuring wellbeing, before drawing on ideas of objective and subjective wellbeing to examine whether these concepts from different disciplines align or oppose one another. Contrasting theories within the literature justify this focus. By testing for associations between objective and subjective wellbeing outcomes, this study highlights how the methodological and conceptual choices made when measuring wellbeing can result in differing conclusions. Despite statistically significant associations being found amongst some wellbeing measures, results which show opposing outcomes highlight how subjective and objective wellbeing are not entirely interchangeable. Our study concludes there is a benefit to incorporating both objective and subjective measures in research and development targets across multiple scales to more-comprehensibly capture, and improve our understanding of, human wellbeing in vulnerable locations.