Position a rack in the center of your oven and preheat to 375 degrees F. Line a baking sheet with parchment paper or a silicone mat.

In a large bowl, whisk together the olive oil, granulated sugar, and brown sugar until well combined and glossy, about 1 minute. The mixture will look like wet sand. Add the egg and vanilla and whisk vigorously until the mixture is smooth and slightly thickened, about 30 seconds.

Add the flour, baking soda, and salt directly to the bowl. Switch to a rubber spatula and stir until just combined with no dry streaks remaining. Do not overmix. The dough will be soft and slightly oily - this is correct.

Add the chocolate chips and fold in until evenly distributed throughout the dough.

Using a cookie scoop or tablespoon, portion dough into 1.5-inch balls and place 2 inches apart on the prepared baking sheet. Bake until the edges are set and golden brown but the centers still look slightly underdone, 10 to 12 minutes. The cookies will look puffy when they come out.

Let the cookies cool on the baking sheet for 5 minutes - they will fall and crackle on top as they cool. Transfer to a wire rack to cool completely. Sprinkle with flaky salt while warm if desired.