This paper examines the work motivations and incentives of employees and self-employed workers near retirement age. We use a sample of Canadians 50 years and older taken from LISA, the Longitudinal and International Study of Adult. Results are as follows. Poverty is associated positively with the transition from employment to self-employment after 50. Optimism appears to explain in part why employees decide to do the switch. For respondents who were self-employed at least once between 50 and 64 years old, it appears that having had prior self-employment experience does not reduce signiﬁcantly the probability of being poor after 65.