Nearly 40% of British self-employees are homeworkers. Using a large representative sample of the UK longitudinal survey data, we explore the determinants of self-employed homeworking, distinguishing between genders. We reject the notion that homeworking is a transitional entrepreneurial state that the self-employed “grow out of”, while establishing that both employer status and business structure play an important role in predicting which self-employed become homeworkers. Our findings also shed light on two outstanding puzzles in entrepreneurship scholarship: why so few of the self-employed create jobs for others, and why on average the self-employed suffer an earnings penalty compared with employees.