This work examines the motivational and cultural underpinnings of financial decision making under risk and uncertainty, using regulatory fit theory, self-regulatory focus theory, self-construal theory, and prospect theory. Based on a comprehensive review of the literature, a theoretical model is proposed that seeks to resolve existing conceptual questions and debates. Central predictions of the model are the differential implications of two different types of fit, i.e., incidental fit and integral fit, for processing mode (intuitive versus systematic), motivational experiences (feeling right versus task engagement) as well as use of different types of information (emotions versus objective factors). In two experiments, with and without incentives, incidental fit but not integral fit results in more risk-neutral choices maximizing monetary outcome. Yet, systematic processing is not consistently related to better decision outcomes, i.e., incidental fit improves decision making independent of processing mode. The proposed model should be useful to Psychologists, Business Administrators, and Economists, or anyone else who wonders about current debates in judgment and decision making.