Explanations of adult involvement in sex work typically adopt one of two approaches. One perspective highlights a variety of negative experiences in childhood and adolescence, including physical and sexual abuse, family instability, poverty, associations with “pimps” and other exploiters, homelessness, and drug use. An alternative account recognizes that some of these factors may be involved, but underscores the contribution of more immediate circumstances, such as current economic needs, human capital, and employment opportunities. Prior research offers a limited assessment of these contrasting claims: most studies have focused exclusively on people working in the sex industry and they have not assessed the independent effects of life course variables central to these two perspectives. We add to this literature with an analysis that drew on insights from life course and life-span development theories and considered the contributions of factors from childhood, adolescence, and adulthood. Our comparative approach examined predictors of employment in sex work relative to two other low-income service or care work occupations: food and beverage serving and barbering and hairstyling. Using data from a study of almost 600 workers from two cities, one in Canada and the other in the United States, we found that both immediate circumstances and negative experiences from early life are related to current sex work involvement: childhood poverty, abuse, and family instability were independently associated with adult sex work, as were limited education and employment experience, adult drug use, and marital status.