Taking a dynamic perspective on goals and their representation over the course of goal pursuit, we explore shifts in goal orientation, particularly when encountering setbacks during goal pursuit. In general, goals can be oriented toward achieving gains, maintaining a current state, and avoiding a loss (i.e., goal orientation; Freund & Ebner, 2005 ). Existing research on goal orientation has focused on age-related differences in goal orientation but assumed that goal orientation is stable over the course of goal pursuit. Taking a short-term, dynamic approach focusing on changes in goal orientation during the pursuit of a given goal, we propose that goal orientation can shift depending on goal progress and the perceived likelihood to achieve the desired outcome. In particular, we suggest that goal orientation remains stable during goal pursuit when progress occurs at the expected rate. However, when goal progress is hampered by setbacks or failures, we propose that people are more likely to shift their orientation toward the avoidance of failure or loss, particularly when they pursue their goal with a backup plan in mind ( Napolitano & Freund, 2016 ). Similarly, when progressing unexpectedly fast in counteracting a loss, we posit that people likely shift from a loss to a gain orientation. After proposing foundational processes for motivational shifts during goal pursuit, we discuss how a “motivational shift” perspective can impact future work on self-regulation and goal striving.