Representative learning design (RLD) in sport is a well-established concept in both theory and practice. The goal of RLD is to faithfully replicate competition environments in training settings to benefit improvement in athletic performance. There is currently little research that considers how representative an activity needs to be to facilitate learning transfer, and how that level of representativeness might fluctuate between activities or sessions, and across competitive cycles. Similarly, there is no existing research that specifically considers the elevated workload (in cognitive and physical load) of highly representative training, and the potential impacts of chronic overuse of these highly demanding activities. This paper addresses these limitations, making a case for the application of RLD that considers the level of representativeness (fidelity) and the demands placed on athletes (load) from both a cognitive and physical perspective. This paper also suggests several categorisations of training activities that are based on their relative representativeness, level of imposed demands, and the intended outcomes of the activity with reference to the perception–action cycle. The two core concepts of fidelity and load are combined for a new approach to representative training that allows practitioners to balance the benefits of representative training with the risks of imposing excessive load on athletes.