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Planning is a crucial tool that employees use to organize their work activities. From the perspective of work and organizational psychology, planning (i.e., mentally simulating possible goal-directed actions along with their potential consequences) is a key component of work-related self-regulation and facilitates goal achievement at work. Yet, the boundary conditions for effective planning remain poorly understood, which is reflected in inconsistent empirical findings on its effects. While some studies show positive effects on performance and well-being, others report null or even adverse effects. This dissertation investigated the boundary conditions of planning effectiveness at work in four empirical studies. Study 1 used a meta-analytical approach to test potential moderators such as differences in planning strategies and contexts. Studies 2 and 3 tested the effects and underlying mechanisms of implementation intentions, a planning strategy commonly used outside the work context that involves making concrete plans to initiate goal-directed behaviors at specific times or locations. Specifically, these studies examined the applicability of this strategy to work-related contexts. Study 4 explored potential adverse effects of planning on work-related well-being, considering goal failure versus goal achievement as a moderator. Overall, the four studies show that planning benefits work performance and well-being, though its effects depend on context and the specific planning strategy involved. Implementation intentions can help achieve specific goals, such as establishing beneficial work habits. However, their effects on general performance are limited. Additionally, planning can negatively impact well-being when goals are not met despite prior planning. Employees should, therefore, consider context, choose planning strategies purposefully, and anticipate setbacks by integrating coping options into their plans.