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This study addresses the scarcity of research on health developments in the heterogeneous group of self-employed workers. It aims at understanding typical health progressions in this group and associations with demographic factors, work characteristics, and self-employment decisions. We investigate health profiles based on mental health problems, self-rated health, and work satisfaction, as well as transitions between them in relation to work effort, reward, overcommitment, demographic characteristics, and entrance and exit into self-employment. Using latent transition analysis, we analyzed data from the Swedish Longitudinal Occupational Survey of Health (SLOSH), including data from 593 participants. We identified four distinct, stable health profiles, revealing associations with work effort, reward, overcommitment, and self-employment decisions. No meaningful relations existed for demographic characteristics. Overall, the findings offer a comprehensive perspective on the health dynamics of self-employed individuals, their associations with work characteristics and decisions to enter and exit self-employment.