Perspective taking is encouraged by organizations as a form of supporting coworkers. Yet, its impact on employees' and coworkers' well-being is not well understood. We, therefore, take a dyadic approach to understand the daily dynamics of employees' perspective taking, its benefits for coworkers, and its costs for employees themselves. Specifically, we draw from self-regulation theory to examine the double-edged sword of perspective taking for one's own and one's coworker's well-being (reflected by subjective vitality). With regard to coworker well-being, we take an other-oriented resource lens and theorize that the focal employee's perspective taking increases the coworker's received support and well-being. With regard to the focal employee's well-being, we take a self-oriented resource lens and theorize that perspective taking increases the focal employee's self-regulatory resource depletion, which impairs their well-being. We examined our research model in a dyadic experience sampling study with three daily measurement occasions over 2 working weeks in a sample of 89 coworker dyads (178 individuals). Multilevel analyses showed that perspective taking had a positive indirect effect on coworker well-being via received coworker support, while it had a negative indirect effect on the focal employee's well-being via self-regulatory resource depletion. (PsycInfo Database Record (c) 2024 APA, all rights reserved).