This article looks at the strategies that influence healthy ageing at work from the motivational theory of life span development (MTD). It aims to better understand the influence of job crafting as a selective primary control, help-seeking as a compensatory primary control, positive reappraisal as a selective secondary control, and downward social comparison and downgrading expectation as a compensatory secondary control on healthy ageing at work (work engagement, health, and motivation to continue working after retirement). A total of 386 educational personnel participated in the study. This study used hierarchical regression analysis to test incremental validity, supplemented with confirmatory factor analysis and structural equation modelling as a solution to solve the potential error problems caused. The results show that job crafting is positively correlated with healthy ageing at work. Positive reappraisal and downward social comparison showed incremental validity in predicting healthy ageing at work beyond job crafting among the middle-aged group (45–65-years-old); in particular, positive reappraisal was the determinant of healthy ageing at work among the middle-aged group. However, both help-seeking and downgrading expectation did not show incremental validity. This study can contribute to the evolution of career development interventions and human resource management focused on supporting older people at work.