As workers age, their choices about whether to continue working and in what capacity can greatly influence their later life economic security and wellbeing.  Workers increasingly choose self-employment as they age, but there are substantial disparities in self-employment activities across demographic characteristics.  This paper examines disparities in the extent and nature self-employment by using novel internal data in the 2016 Health and Retirement Study (HRS) to classify self-employment of older adults in the United States into roles (own/run; manage; independent).  Using the classification along with the breadth of information collected in the HRS, this work finds substantial differences in demographic characteristics, work characteristics, income, and benefits, as well as substantial variation in quality of life and retirement expectations by role.  Further work linking to administrative records suggests substantial discrepancies between survey responses and administrative records.