Contemporary retirement research endeavours to identify the complex antecedents and consequences of retirement decisions and retirement planning. However, few research studies have examined how retirement decisions and planning behaviours have been implemented, nor has there been any significant research investigating the impact of the complex interactions that occur between individual traits and matching or non-matching strategic preferences on retirement outcomes. This research programme addresses these shortcomings by applying the theories of regulatory focus and regulatory fit (Higgins, 1997,2000) to a model designed to examine the relationship between individual chronic motivational orientations and the means of pursuing retirement preparation strategies and their influence on pre-retirement anxiety and affect. In three studies a set of approach and avoidance strategies are elicited and tested as moderators of the relationship between an individual’s chronic regulatory orientation, measured by general regulatory focus measure strength (GRFMS) and their pre-retirement anxiety (measured by the Social Components of Retirement Anxiety SCRAS) and positive and negative affect(measured by the PANA Schedule). Overall, the three studies support the application and adaptation of the regulatory focus and regulatory fit approach to a greater understanding of the interaction between motivational orientation and means of pursuing retirement preparation goals. Results indicate that it is possible to differentiate retirement preparation strategies into distinguishable groups of approach and avoidance strategies. Results also demonstrate that a “fit” versus a “non-fit” between chronic orientation and the type of strategies pursued can improve outcomes for those approaching retirement. Results from Study 3 shows that regulatory orientation coupled with the type of strategies chosen explained significant variance in pre-retirement anxiety and positive and negative affect. Specifically, the type of strategies chosen significantly moderated the relationship between regulatory orientation and both preretirement anxiety and negative affect. The moderation effect on the relationship between regulatory orientation and positive affect was not statistically significant. One unexpected result indicated that for chronic prevention orientated individuals a match might in fact exacerbate their negative reactions rather than decrease them. Results from this research helps to further explain the consequences of planning behaviours by demonstrating that a fit between individual differences and specific means of goal pursuit, as proposed by regulatory fit theory, does impact on outcomes such as anxiety and affect. The implications of these results, for research in retirement, self-regulation and questionnaire development, are suggested.