Despite a rich literature on goals, the notion of successful goal pursuit remains somewhat unclear. Most research on personal goal pursuit relies on subjective measures of goal progress and research that uses objective measures (e.g., grade point average) often ignores individuals’ idiosyncratic goals. The present research investigated the relation between diverse measures of goal progress in the context of academic and weight loss goals using four datasets (total sample = 351). Overall, subjective measures were positively related to objective measures. The magnitudes of these associations varied across studies and were generally smaller than would be expected if the measures assessed the same construct (R² = .05–.39). These findings suggest that subjective and objective measures may reflect related but distinct constructs. The present research draws attention to an important topic in the goals literature and highlights the need for additional research on the conceptualization and operationalization of successful goal pursuit.