Heat 1 tbsp olive oil in a Dutch oven over medium-high heat. Season beef cubes with salt and pepper and sear in batches until browned on all sides, about 3–4 minutes per batch. Remove beef and set aside.

In the same pot, add remaining olive oil if needed. Sauté onion, celery, and carrots for 5 minutes until softened. Add garlic and cook 1 minute until fragrant.

Pour in red wine, scraping the bottom of the pot to lift browned bits. Reduce wine by half over 2–3 minutes.

Add beef broth, Worcestershire sauce, fresh thyme, and seared beef back to the pot. Bring to a boil, then reduce heat to low. Simmer uncovered for 45 minutes.

Stir in pearled barley and continue simmering 45–60 minutes until barley is tender and soup has thickened slightly, stirring occasionally.

Adjust seasoning with salt and pepper. Remove thyme sprigs and stir in chopped parsley for a fresh, aromatic finish.