Preheat the oven to 350 degrees F.
To a stand mixer, add the butter, brown sugar and granulated sugar. Blend on high with the paddle attachment until the sugar granules are less visible and the mixture is light and fluffy, about 4 minutes.
Scrape the sides with a rubber spatula, then add the egg and blend on low until combined, stopping to scrape the sides more to incorporate.
Prepare the dry ingredients. In a separate bowl, add the flour, pumpkin pie spice, baking powder and baking soda. Stir and toss with a spoon or fork.
Scrape the sides of the mixer bowl and, while off, add half of the flour mixture. Turn on low and mix until combined; this should only take 5 to 6 rotations of the paddle. Stop and scrape the sides again, then add the other half of the flour and mix on low the same way. Turn off the mixer.
Add the chopped chocolate chips and crushed candy canes. Turn the mixer back on low and blend until just combined; this should only take 3 to 4 rotations of the paddle.
Line 3 baking sheets with parchment paper. Scoop dough balls the size of golf balls, 1 tablespoon each, and place 3 inches apart on the baking sheet, about 8 cookies per sheet. Bake until the edges are set and the center is cooked through, but still soft, 13 to 15 minutes.
Cool the cookies for 2 to 3 minutes on the sheets. Then, holding the baking sheet over a wire cooling rack, remove the cookies from the sheet by gripping the baking sheet with one hand and the parchment paper on the opposite side with your other hand. Gently slide the parchment paper off the sheet with the cookies still on top, resting the parchment and cookies on the wire rack beneath until cool. This cookie removal/cooling trick takes coordination, so think about it before you do it and easy on the egg nog.