The pursuit of happiness has preoccupied philosophers, psychologists, and consumer researchers, amongst others. Recently, the pursuit of happiness has been investigated empirically, with results appearing to support the perspective that explicitly trying to enhance one’s own happiness may be counterproductive. However, prior investigations were often correlational or involved participants being asked to monitor their happiness under constrained conditions (e.g., while engaging in tasks assigned to them by an experimenter). The current research endeavors to address this limitation, and build a broader framework for understanding when the pursuit of happiness may be effective. In line with prior work, we find that when consumers are asked to monitor their own happiness, they often experience a decrease in happiness regardless of whether their experience is constrained or not. However, when individuals adopt a behavior-focused happiness goal, and are given the freedom to engage in behaviors of their choosing, they tend to modify their behaviors in a way that improves their overall happiness. We relate our findings to prior research regarding why individuals often fail to make happiness-enhancing choices and discuss the practical implications these results may offer for improving consumer welfare.