This paper examines the relationships between two independent regulatory mode orientations, locomotion and assessment, and well‐being in organizational contexts. Results from a sample of 320 employees revealed that locomotion was negatively associated with burnout and psychological strain whereas assessment was positively associated with burnout and strain. The effects of locomotion and assessment on burnout and strain were mediated by workaholism and work engagement. Both locomotion and assessment predicted greater workaholism; however, locomotion was positively associated whereas assessment was negatively associated with work engagement. In turn, workaholism predicted greater burnout and strain, and work engagement predicted less burnout and strain. Implications for employee health and organizational success are discussed.