Preheat oven to 350 degrees. Line 2 large baking sheets with parchment paper.
With a hand mixer or stand mixer, or a whisk if you'd like an arm workout, cream brown sugar and butter until whipped and soft, about 2-3 minutes. Add in tahini, the egg, vanilla extract, and bourbon. Beat until fluffy, about 1 minute more.
In a separate small bowl, combine flour, baking soda, cinnamon, and kosher salt. Add dry ingredients to wet and mix until mostly combined. Fold in chocolate chips.
Measure a rounded tablespoon worth of dough onto prepared baking sheets, leaving about 2 inches of space between them. I fit 8 cookies comfortably on my large baking sheet and I wouldn't recommend any more than that.
Bake 8 minutes. Remove cookies from oven and tap the baking sheet a few times on the counter - this encourages spread and that gooey crinkly texture I so adore in a cookie. Place back into the oven for an additional 2-3 minutes, until centers are set and edges brown slightly.
Allow cookies to cool on the baking sheet for about 10 minutes, then either eat a warm cookie or five, or transfer to a wire rack to cool completely. Cookies can be stored refrigerated in an airtight container for up to a week, on the counter for 3-5 days, or in the freezer for up to 3 months.