Does being (very) well-off enhance our sense of well-being? This paper explores the role of well-being in the workplace by reconsidering the pervasive assumption that more income leads to greater happiness. It cites a number of examples in the current economic downturn where companies’ offering of choices to employees about their form of compensation resulted in lower costs, greater work-life balance and employee retention, and a general increase in well-being. As firms seek to increase employee engagement, these types of cases can prompt us to rethink our assumptions about what the real hierarchies of needs are in our organizations and how rewards of all types affect performance.