Season the beef. Pat the beef dry with paper towels, then season generously on all sides with kosher salt and black pepper. For a 3 lb chuck roast, I recommend 2 tsp kosher salt and ½ tsp black pepper. Allow the beef to come to room temperature for about 20 minutes before cooking.
Sear the chuck roast. Preheat an oven to 325°F (163°C) with a rack set just below the middle. Heat 2 Tbsp neutral oil in a large Dutch oven over medium-high heat. When hot, add the beef pieces (working in batches so as not to overcrowd the pan) then cook undisturbed for about 3-4 minutes per side, until seared on all sides. Transfer to a plate, then repeat as needed.
Render bacon. To the pan, add bacon lardons then cook, stirring occasionally, until the fat begins to render, about 3 minutes.
Add vegetables. Add shallots, carrots, and 5 smashed garlic cloves, then cook for another 3-4 minutes. Stir in 2 Tbsp tomato paste and 2 tsp anchovy paste, then cook another few minutes until they take on a little color. Sprinkle with 2 Tbsp flour, stir well, then cook 1 minute more.
Make the braising liquid. Pour in 2 Tbsp Cognac (or Brandy) and 2 cups of dry white wine. Whisk in 1 Tbsp Dijon mustard, then return the beef to the pan along with any juices. Add enough beef broth (or water) to just come up most of the way to the top of the beef (about 2 cups).
Add herbs. Using kitchen twine, tie together the thyme and rosemary sprigs, then add these to the pot along with 1 dried bay leaf and 3 orange peel strips. Place a sheet of parchment paper or aluminum foil directly on top, pressing down slightly so it stays in place, then cover with a tight fitting lid.
Braise the beef. Transfer to the oven, then cook for 2½-3 hours. You’ll know the beef is done when it’s completely fork tender and shreds easily. The carrots should be tender. Carefully remove, then stir in ½ cup (90g) black olives and allow to sit for just a minute or two until heated through.
Reduce the sauce. Transfer the beef and vegetables to a large serving platter with a slotted spoon, leaving behind the braising liquid. Discard the herbs. Place the pot over high heat, bring to a boil, then simmer until the liquid has reduced, about 6-8 minutes.
Finish, then serve! Plate in wide shallow bowls over polenta, mashed potatoes, or pasta. I like to add the beef and vegetables first, then spoon the sauce directly on top. Finish with a pinch of flaky sea salt, freshly cracked black pepper, and chopped fresh parsley. Enjoy!