Tasks such as the elimination of all debts when faced with the immediate option to spend can be unpleasant but not conceptually difficult. Dividing these tasks into smaller parts and completing the parts from smallest size to largest size can help people realize quick motivational gains that increase their likelihood of completing the task. The authors more broadly define this idea as small victories and discuss, model, and empirically examine two related behavioral theories that might explain it. A laboratory experiment tests this prediction and provides data for model calibration. Consistent with the idea of small victories, when a task is broken down into parts of unequal size, participants perform faster when the parts are arranged in ascending order (i.e., from smallest to largest) rather than descending order (i.e., from largest to smallest). The calibrated model is consistent with the directional predictions of each theory. However, when participants are given choice over orderings, they choose the ascending ordering least often. The authors conclude with a discussion of the efficacy of this method in stylized debt-repayment scenarios.