Nowadays the freedom to make choices is considered of vital importance for decision-makers. Researchers investigating the psychological effects of choice provided empirical evidence about the many advantages of choice (i.e., increased intrinsic motivation, greater perception of self-determination, better performance, and greater life satisfaction). However, more recent studies demonstrated the downsides of choice. When the decision task difficulty exceeds the natural cognitive resources of human mind, the possibility to choose becomes more a source of unhappiness and dissatisfaction than an opportunity for a greater well-being. We here discuss in a detailed fashion the main findings of research in psychology and consumer behavior showing the bright sides and the downsides of choice.