The social ordering of time within a changing workplace is a serious concern for scholars, employers, and employees alike. This study contends that the use and evaluation of free time will reduce feelings of overwork brought on by the characteristics and pressures of work. I use the stress of higher status perspective that posits workers in jobs with autonomy and schedule control are also more likely to experience high work demands and work-nonwork interference. I extend this perspective to test the relationship among high-status job characteristics and feeling overworked. Further, I use the free time as resistance perspective that posits free time can be used to actively challenge the way power is exercised. Finally, because temporal experiences are gendered, I predict the effects of free time use and evaluation differ between women and men. The results of this study provide mixed support for these perspectives. It is clear that job pressures and demands lead to feeling overworked, however characteristics such as schedule control, income, and work skills do not increase feeling overworked. Further, the buffering effect of free time is different for free time use and free time evaluation. Specifically, free time use does not have much of a buffering effect. Free time evaluation, however, does buffer the effects of certain job pressures. Moreover, certain effects of free time evaluation on job characteristics differ by gender (autonomy and work pace). Together, the findings provide insights into the relationship between feeling overworked, free time, and gender.