This study compares personal values and forms of happiness between self-employed workers and those employed in an organization. Values are examined through Schwartz’s (1999) established model, and happiness is measured in terms of personal flourishing and both job-specific and general hedonic well-being. In two nationally representative samples, self-employed workers are found to value self-direction and stimulation in their lives to a significantly greater degree than do organizational employees, but not to differ in other types of value. Well-being differences are predicted to depend on whether or not workers supervise others, such that any well-being advantages of self-employment are expected to occur only for self-employed workers without subordinates. As predicted, job satisfaction in self-employment is found to exceed that of organizational workers primarily for those who do not supervise others. In respect of personal flourishing, self-employed workers report significantly greater accomplishment in their lives, and that difference is again found only for workers without supervisory responsibility. However, strain experienced in a job and context-free hedonic well-being are found to be similar between self- and organizational employment. Refinements are proposed to research methods and practical procedures.