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.