To the bowl of a stand mixer fitted with the paddle attachment (or large mixing bowl and electric mixecombine the butter, sugars, egg, vanilla, and beat on medium-high speed until well combined, about 2 minutes.
Stop, scrape down the sides of the bowl, and add the flour, pudding mix, baking soda, optional salt, and beat on low speed until just combined, about 1 minute.
Stop, scrape down the sides of the bowl, and add the chocolate chips, and beat on low speed until just combined, about 30 seconds. Mixture will look shaggy and like shredded Play-Doh bits, and is both oily and dry; this is okay.
Using a large cookie scoop, 1/4-cup measure, or your hands, form approximately 12 equal-sized mounds of dough by compressing, compacting, and squeezing until the dough comes together; don’t be afraid to really squeeze it. If your dough is absolutely not coming together, and is fluffy, fuzzy, or seemingly too dry, drizzle in one tablespoon of coconut oil at a time until it comes together. Do this as a last resort because it can make the dough oily in a hurry. The chips are prone to falling out, but just keep pushing them back in.
Place mounds on a large plate or tray, flatten slightly (when properly chilled, cookies don’t flatten much while baking so flatten them now), cover with plasticwrap, and refrigerate for at least 3 hours, up to 5 days. Do not bake with unchilled dough because cookies will bake thinner, flatter, and be more prone to spreading. Make sure the cookies are in the exact shape you want them before chilling, because it’s exceedingly difficult to re-shape them after chilling.
Preheat oven to 350F, line a baking sheet with a Silpat or spray with cooking spray. Place dough mounds on baking sheet, spaced at least 2 inches apart (I bake 8 cookies per sheeand bake for about 11 minutes, or until edges have set and tops are just set, even if slightly undercooked, pale, and glossy in the center; don’t overbake. Cookies firm up as they cool. Allow cookies to cool on baking sheet for about 10 minutes before serving. I let them cool on the baking sheet and don’t use a rack.
Cookies will keep airtight at room temperature for up to 1 week or in the freezer for up to 6 months. Alternatively, unbaked cookie dough can be stored in an airtight container in the refrigerator for up to 5 days, or in the freezer for up to 4 months, so consider baking only as many cookies as desired and save the remaining dough to be baked in the future when desired.
