This study investigated the extent to which cognitive measures of individual differences predict strategy shifts in a series of procedural-motor curve-drawing tasks. College students participated in a task which required them to trace or draw various forms of a figure-8 before completing a battery of cognitive tests. Three distinct drawing strategies emerged, and the tendency to vary these strategies was quantified using Shannon’s Entropy. The results indicated that participants employed multiple strategies early in a block of trials before eventually settling on a preferred strategy. Additionally, higher creativity scores were associated with higher entropy, whereas participants with higher verbal and working memory ability preferred to settle on their preferred strategy.