Remove chuck roast from refrigerator 30 minutes before cooking. Cut into 1-inch cubes, trimming large pieces of hard fat. Pat beef cubes thoroughly dry with paper towels and season generously with salt and pepper.
Heat Dutch oven over medium-high heat with 1 tablespoon oil. Add beef cubes in a single layer without crowding. Cook undisturbed 3-4 minutes until a dark brown crust forms, flip and cook another 2-3 minutes. Transfer browned beef to a plate using a slotted spoon. Add remaining oil and repeat.
Reduce heat to medium. Add diced onion to the pot and cook 4-5 minutes until softened. Add garlic and cook 60 seconds until fragrant. Add mushrooms and cook 3-4 minutes until they release liquid and soften. Push vegetables aside, add tomato paste to center and cook 1-2 minutes until darkened.
Pour in 1 cup of beef broth (or red wine if using) and scrape up all browned bits from bottom of pot. Add remaining 7 cups broth, water, Worcestershire sauce, bay leaves, thyme, rosemary, and smoked paprika. Return browned beef and any juices to the pot. Bring to a boil over high heat.
Once boiling, stir in pearl barley. Reduce heat to low, cover with lid slightly ajar, and simmer 30 minutes, stirring occasionally to prevent sticking.
After 30 minutes, add sliced carrots, celery, and diced potatoes. Stir to distribute. Replace lid slightly ajar and continue simmering over low heat another 25-30 minutes until vegetables are fork-tender, barley is cooked, and broth has thickened.
Remove and discard bay leaves. Taste soup and adjust seasoning with salt and pepper. If too thick, add a splash of hot water or broth. Ladle into bowls, garnish with fresh parsley, and serve with crusty bread.