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Strip the kale from its stems and tear into bite-sized pieces. Wash and dry well in a salad spinner.
Heat the olive oil over medium-high in a 12-inch frying pan. Add garlic, salt, and red pepper flakes and cook, stirring frequently, for a minute or two, until garlic is very fragrant and beginning to take on the slightest bit of color.
Add kale by the handful. Pan will be very full at first.
Cook, stirring very frequently at first, until kale is tender and dramatically reduced in volume. Depending on the variety and thickness of the kale you're working with, this will take anywhere from a couple of minutes to more like 10 minutes. Add 1 tbsp balsamic vinegar now if not using glaze and stir during the last few minutes of cooking.
Off the heat, stir in the parmesan and drizzle with balsamic glaze.