Use paper towels to thoroughly pat the beef chuck chunks completely dry on all sides, ensuring clean searing mechanics. Season the meat generously with salt and black pepper.

Heat 1 tablespoon of the olive oil in a large, heavy-bottomed Dutch oven or stockpot over high heat. Once the oil begins to shimmer, drop in the beef pieces in a single layer and sear undisturbed for 3 to 4 minutes until a deep brown crust locks onto the bottom surface; flip and color the edges for another 2 minutes, then transfer the meat to a clean plate.

Drop the remaining 1 tablespoon of olive oil into the empty, hot pot, dropping the stove heat down to medium. Toss in the diced yellow onion, sliced carrots, and celery, cooking for 6 to 8 minutes while stirring frequently until the vegetables soften and become highly aromatic.

Add the minced garlic straight into the center of the pan, mashing and stirring it against the hot metal surface for exactly 60 seconds until fragrant, taking care not to let the garlic bits scorch.

Pour the diced tomatoes with their juices, beef broth, and Worcestershire sauce directly into the pot, stirring firmly with a wooden spoon to scrape up all the dark, caramelized savory beef bits anchored to the bottom of the vessel.

Stir in the uncooked rinsed pearl barley, dried thyme, dried bay leaf, and the seared beef chunks along with any collected plate juices, mixing until the ingredients are uniformly suspended in the liquid baseline.

Bring the soup up to a rolling boil over medium-high heat, then immediately drop the flame down to low to maintain a gentle, steady simmer. Clamp a tight lid securely over the top and let the pot simmer undisturbed for 55 to 60 minutes.

Lift the lid and taste a barley grain; the soup is finished the exact moment the beef is meltingly tender and the barley cells have plumped up into a soft, slightly chewy bite. Turn off the flame, discard the bay leaf, adjust with additional salt or pepper if desired, and ladle hot into deep bowls.