This work examines the nature of self-employment arrangements of older adults in the United States.  The project leverages novel restricted-access data collected in the Health and Retirement Study (HRS) in 2016 on the employer names and locations for individuals reporting self-employment along with respondent narratives on industry and type of work to classify self-employment reports into three entrepreneurial roles (own/run; manage; independent) across 14 different types of work.  Using the breadth of information collected in the HRS and linkage to administrative records, I compare differences in characteristics, such as demographics, income, wealth, savings, health insurance coverage, home ownership, health status, and expectations of working longer, associated with different classifications of self-employment.  Exploring characteristics of self-employment provides unique insights into the changing nature of work and the transition to retirement relevant to policy considerations across the health, insurance, and retirement income dimensions, among others.