The self-regulatory strategy of mental contrasting a desired future with obstacles of reality instigates goal-directed behavior when expectations of success are high and curbs goal-directed behavior when expectations are low (Oettingen, 2000). Two studies show that mental contrasting paired with high expectations of success creates strong associations between obstacles of reality and behavior instrumental to overcome these obstacles; mental contrasting paired with low expectations of success leads to weak associations. Reverse contrasting and irrelevant content control conditions did not produce expectancy-dependent associations between obstacle and instrumental behavior. Importantly, the strength of these associations mediated mental contrasting effects on goal-directed behavior (Study 2).