It has become well established in laboratory experiments that switching tasks, perhaps due to interruptions at work, incur costs in response time to complete the next task. Conditions are also known that exaggerate or lessen the switching costs. Although switching costs can contribute to fatigue, task switching can also be an adaptive response to fatigue. The present study introduces a new research paradigm for studying the emergence of voluntary task switching regimes, self-organizing processes therein, and the possibly conflicting roles of switching costs and minimum entropy. Fifty-four undergraduates performed 7 different computer-based cognitive tasks producing sets of 49 responses under instructional conditions requiring task quotas or no quotas. The sequences of task choices were analyzed using orbital decomposition to extract pattern types and lengths, which were then classified and compared with regard to Shannon entropy, topological entropy, number of task switches involved, and overall performance. Results indicated that similar but different patterns were generated under the two instructional conditions, and better performance was associated with lower topological entropy. Both entropy metrics were associated with the amount of voluntary task switching. Future research should explore conditions affecting the trade-off between switching costs and entropy, levels of automaticity between task elements, and the role of voluntary switching regimes on fatigue.