This study explores the relationship between fit and satisfaction. More specifically it examines the congruence problem - the weaker than expected relationship between a good occupational fit (also referred to as congruence) and higher levels of work satisfaction. Using John Holland’s prominent and influential Theory of Vocational Choice as a framework, this research sought individual perspectives from workers who do not conform to expectations of fit theory, in that they are either measured as a good fit for their occupation and unsatisfied, or measure as a poor fit and yet are satisfied at work. This study analysed workers in this anomalous situation to understand how their experience of work links to, and helps to highlight, limitations in current occupational fit approach. 253 UK workers, in occupations spanning across all major categories, were measured for satisfaction and fit with their current occupation using a RIASEC work personality assessment. From this initial assessment, 39 of those workers with the largest measured disparity between fit and satisfaction were identified. Using semi-structured interviews, these participants were asked to describe a wide range of work experiences, including those relating to satisfaction, their occupations, and perceptions of fit and adjustment. Thematic Analysis was used to identify common and important aspects of their lived experiences that helped explain the congruence problem. Several explanations of the congruence problem emerged from this analysis. Firstly, elements that are measured in Holland’s approach appear to have important sub-elements that are not considered, or not considered sufficiently. In some cases, part of the current fit calculation mechanism was found to be insufficiently detailed to allow meaningful measurement. This research also identified several factors important to work satisfaction that fall outside Holland’s scope of fit measurement. There are also elements that themselves defy expectations of fit theory, such as the satisfaction ...