Research in psychology, economics, and management has shown that individuals are pushed or pulled into different forms of multiple jobholding (MJH), e.g., moonlighting, second jobs, portfolio careers, and hybrid entrepreneurship, and that their work experiences are depleting or enriching (Campion et al., 2020). While several researchers assumed that the type of motivation determines multiple jobholders’ wellbeing, the specific motivational content and mechanisms by which MJH motivation may affect individuals' work-related wellbeing have rarely been investigated (Campion & Csillag, 2021; Cohen, 2020; Sliter & Boyd, 2014). In order to describe and explain how individuals’ motivation influences their work-related wellbeing in MJH, this study examines why individuals work more than one job at a time, why they work their specific jobs, why they work their specific combination of jobs, and how their motivation relates to their work-related wellbeing. Adopting a resource-based lens (Bakker & Demerouti, 2017; Hobfoll et al., 2018), 30 semi-structured interviews from a heterogeneous sample of MJHers were analyzed in a person-centered approach in a qualitative content analysis (Kuckartz, 2014). Based on the constructed multi-level multi-job motivational profiles, the Holistic Multi-Job Motivational System Framework was developed. The findings reveal that MJH motivation is organized as a system that spans all jobs in a multi-job portfolio. The framework explains how a large motivational potential emerges beyond the aggregated motivation for each job that determines wellbeing. Moreover, the findings show how MJHers proactively optimize their motivational system for wellbeing through three strategies: Resources and demands management, multi-job crafting, and multi-job portfolio crafting.