Comfort is a big factor in a headset. Look for a headset with premium foam cushioning that has more give and lasts longer. Another option is to replace the cushions entirely. Some of the top-tier headsets allow for this. The trade-off may be a slight reduction in sound quality. Consider the weight of your current headset as well. Big, heavy ear cups or a too-tight headband could be the reason you feel like you’re fighting the headset. A lighter headset may be the best solution to extending your playing time.