Drawing on gestalt characteristics theory, we advance the literature on the effect of job complexity on employee well‐being by considering intra‐individual variability of job complexity over time. Specifically, we examine how the trend, or trajectory, of job complexity over time can explain unique variance of employee job strain. Across two longitudinal data sets, we consistently find that, with the average level of job complexity during a given period held constant, a positive job complexity trajectory (i.e., an increasing trend in complexity) is associated with higher employee job strain. Based on job‐demand‐control theory and the exposure‐reactivity model, we further establish that job autonomy and employee emotional stability jointly moderate the relationship between job complexity trajectory and employee job strain. Specifically, for employees with high emotional stability, job autonomy mitigates the job strain brought by positive job complexity trajectory, whereas for employees with low emotional stability, job autonomy does not help to reduce the adverse effect of the increasing trend. These findings not only contribute to extend the understanding of the job complexity – strain relationship, but also suggest a promising, dynamic avenue to study the effects of work characteristics on employee well‐being as well as other outcomes. Copyright © 2016 John Wiley & Sons, Ltd.