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Background The working environment is rapidly changing with flexible working conditions and extended working lives often resulting in ‘non-traditional’ career trajectories. Yet, our knowledge on how such trajectories affects people’s health is limited. Therefore, our aim is to explore common employment history patterns among UK individuals and assess possible associations with health.Methods We used UK Biobank data to construct employment histories and identify working-life patterns across 66 calendar years (1951–2017). Using Sequence Analysis, we produced Sequence Index Plots by gender and age to derive these patterns. Then, we classified respondents based on their employment history using optimal matching and cluster analysis. Generated clusters were used as exposures in logistic regression models to test their association with self-rated health.Results Continuously employed women aged 40–49 had better health than women in the Employed/in education/caring pattern [OR=0.80; CI: 0.69, 0.93], or those off sick at some point in the past [0.68, CI: 0.59, 0.79]. Men aged 40–49 reported worse health if employed and retired early [0.64; 0.53, 0.78] or were off sick in the past [0.42; 0.31, 0.57]. Retirement for women aged 50–69 improves their health, irrespective of multiple gaps or caring responsibilities and short-term employment. However, continuously employed, or continuously employed and then retired men had better health than those in non-continuous employment.Conclusion Continuous employment was associated with better health in men, but not always for women. The modern working environment is rapidly changing, increasingly giving rise to ‘non-traditional’ career trajectories which might result in future adverse health impacts