Preheat & Prep: Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper.
Mix Dry Ingredients: In a medium bowl, whisk together flour, baking soda, and salt.
Cream Butter & Sugar: Beat the softened butter and brown sugar with an electric mixer until fluffy, about 2 minutes.
Add Wet Ingredients: Mix in the bourbon, egg, and vanilla extract until smooth.
Combine Mixtures: Gradually blend the dry ingredients into the wet mixture until just combined. Fold in the chocolate chips gently.
Shape Cookies: Scoop tablespoon-sized portions of dough onto the prepared baking sheet, spacing them about 2 inches apart.
Bake: Bake for 10-12 minutes or until the edges are golden brown.
Cool: Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Prepare Glaze: Dissolve espresso powder in hot water. Whisk in powdered sugar and heavy cream until smooth and pourable.
Glaze the Cookies: Drizzle the glaze over the cooled cookies. Let it set before serving.