Using data from the 2002 National Study of the Changing Workforce (NSCW) (N = 3,504), we examined differences among organizational employment and two categories of self-employment: independent contractors and small business owners. Our results suggest that self-employment, either as owner or independent, may allow individuals to achieve greater autonomy than would be available to them as organizational employees. However, the greater pressure associated with ownership of a small business detracts from the advantages of having autonomy, making small business ownership a double-edged sword. Those working as independent contractors appear to reap the benefits of greater autonomy as well as lower levels of job pressure.