ObjectiveTo investigate trajectories of sustainable working life (SWL, ie, no interruptions or transitions in working life due to sickness absence (SA), disability pension (DP), or unemployment) in Swedish residential regions using a population‐based twin cohort, while assessing sociodemographics and twin pair similarity.MethodsSample of 60 998 twins born in 1925–1958. SWL was assessed through main labor market status in each year in 1998–2016 based on > 180 days with SA/DP, > 180 days with unemployment, or >half of yearly income from old‐age pension for not in SWL, and employment (in paid work and did not fulfill the criteria SA/DP, unemployment, or old‐age pension) for SWL. Residential regions were classified into nine groups based on Swedish municipalities. Group‐based trajectory models and multinomial logistic regression were applied separately for all regions.ResultsIn all regions, the largest trajectory group was sustainable working life. Three to four trajectory groups developed toward unsustainable working life with different exit points from sustainable working life. A small proportion were grouped with partial stable or increase in sustainable working life. Increased age, being a woman, <12 years of education, and history of unstable working life increased, and being married and twin pair similarity decreased the likelihood of belonging to trajectories toward unsustainable working life.ConclusionsIn all regions, most of the individuals followed a sustainable working life trajectory. A reasonable proportion of individuals followed trajectories developing toward unsustainable working life. The influence of sociodemographic and familial factors on trajectory groups was similar in all regions.