Objectives To construct prediction models for transitions to combination multiple job holding (MJH) (multiple jobs as an employee) and hybrid MJH (being an employee and self‐employed), among employees aged 45‐64. Methods A total of 5187 employees in the Netherlands completed online questionnaires annually between 2010 and 2013. We applied logistic regression analyses with a backward elimination strategy to construct prediction models. Results Transitions to combination MJH and hybrid MJH were best predicted by a combination of factors including: demographics, health and mastery, work characteristics, work history, skills and knowledge, social factors, and financial factors. Not having a permanent contract and a poor household financial situation predicted both transitions. Some predictors only predicted combination MJH, e.g., working part‐time, or hybrid MJH, e.g., work‐home interference. Conclusions A wide variety of factors predict combination MJH and/or hybrid MJH. The prediction model approach allowed for the identification of predictors that have not been previously studied.