Cook ½ cup packed light brown sugar, 6 tablespoons unsalted butter, ¼ cup honey, and ¼ molasses in a medium (preferably wide) saucepan over medium-low heat, stirring occasionally until the sugar dissolves and the butter melts, 2 to 3 minutes. Remove the saucepan from the heat.
Stir in 1 teaspoon ground ginger, 1 teaspoon ground cinnamon, ¾ teaspoon black pepper, ½ teaspoon ground nutmeg, ½ teaspoon ground allspice, ½ teaspoon ground cardamom, and ½ teaspoon kosher salt. Set aside, stirring occasionally, until mostly cooled and thickened, about 15 minutes.
Add 1 large egg and ¼ teaspoon anise extract if using, and vigorously mix into the butter mixture with a stiff spatula until shiny and smooth. Sift in 2 ½ cups all-purpose flour and ¼ teaspoon baking soda. Stir until the flour is completely blended. The mixture will look like a very thick batter.
Transfer to a large piece of plastic wrap, wrap, and pat into an even thickness. Refrigerate until firm (it will not be hard) and no longer sticky, at least 4 hours but preferably overnight.
Arrange 2 oven racks to divide the oven into thirds. Heat the oven to 350°F. Line 2 rimmed baking sheets with parchment paper.
Roll 1 heaping teaspoon of the dough into a smooth ball (about 1-inch wide). Continue to roll the dough and place on the baking sheets, spacing the dough balls about 1-inch apart, 30 to 35 per sheet.
Bake for 5 minutes. Rotate the baking sheets between racks and from front to back. Bake until the sides of the cookies are firm, the tops are just set, and the edges have lightly browned, 3 to 5 minutes more (err on underbaking). Let the cookies cool on the baking sheets for 5 minutes, then transfer to a wire rack and let cool completely.
Place ½ cup powdered sugar in a fine-mesh strainer and generously dust over the cookies before serving.
