Actions aimed at achievement of a desider outcome and at avoidance of an undesired one differ in behavioral measures and brain activity, even if these actions are outwardly similar. In our framework, functional systems that subserve behavior for achievement and avoidance are formed within two different domains of individual experience — those of approach and withdrawal — that provide different degrees of differentiation for interaction of individual with the environment. Based on the previously revealed relation between sample entropy of heart beats and the degree of differentiation, we recorded the heart rate of university students during the performance of two tasks on a computer. The tasks were presented in one of two sequences and in one of two motivational contexts for different groups. In accordance with the idea of greater differentiation of the avoidance domain and in correspondence with our previous results, the transfer effect is higher in the achievement context if the tasks are presented without a break. It has been shown that sample entropy differs between analytic and holistic participants, and this difference reflects their structure of experience. No differences were found in sample entropy between the contexts, presumably due to a more pronounced effect of its dynamics during task performance. Comparison of entropy in participants with different levels of individual traits showed that participants with analytical thinking, compared to holistic ones, perform part of one of the tasks faster, and their entropy during task performance starts growing from lower values. We interpret all the results in terms of the temporary decrease in differentiation at the initial stage of learning.