Background: Multiple job holding (MJH) is a common and growing phenomenon in many countries. Little is known about experiences with MJH among older workers. The objective of the present study is to gain insight in experiences with MJH among Dutch workers aged 45 years and older. Methods: Multiple job holders were selected from the Study on Transitions in Employment, Ability, and Motivation (STREAM), a Dutch cohort study among persons aged 45 years and older. Purposive sampling was applied to assure heterogeneity regarding gender, educational level, health, financial situation, willingness to continue MJH, and type of MJH (only jobs as employee or also being self-employed). Interviews were conducted until data saturation occurred. Fifteen multiple job holders participated in this study (eight men, seven women). Interviews were digitally recorded, transcribed verbatim and analyzed, along with field notes, using thematic content analysis. The data were openly coded, after which codes were aggregated into themes, which formed a thematic map. In each phase of the analysis at least two researchers were involved to increase reliability. Results: Experiences with MJH varied from positive to negative. They were influenced by characteristics of individual jobs, e.g. social support at work, as well as characteristics of the combination of jobs, e.g. positive spill-over effects, and conflicts between work schedules. The personal context of multiple job holders, e.g. their age, or reason for MJH, affected how work characteristics influenced experiences. Negative experiences with one job often coincided with negative experience in the other job(s), and problems in the personal context. Some multiple job holders were able to make changes to their situation when desired. For some, this was not possible, which augmented their negative experience. Conclusions: This study adds to existing knowledge that experiences with MJH are not only influenced by work characteristics but also by the personal context of multiple job holders, and that some workers are able to change their situation when desired, while others are not. Future research should study how different combinations of work and personal characteristics influence sustainable employability of multiple job holders. Policies facilitating life-long learning could increase opportunities to change the MJH situation when desired.