This study examines the job satisfaction dynamics of entrepreneurs. Using the Household Income and Labour Dynamic in Australia (HILDA) survey, we evaluate the temporal pattern of anticipation, reaction, and adaptation in job satisfaction occurring before, during, and after the transition into self-employment. Results vary across the different domains of job satisfaction: while entrepreneurship entry induces a short-term boost in overall job satisfaction and satisfaction with the work itself, it has a long-lasting negative impact on satisfaction with income and job security. Further, entrepreneurs exhibit positive adaption to balancing work, non-work commitments, and leisure time. No significant gender differences were identified.