Add two tablespoons of olive to a large pot over medium-high heat, then add the beef chunks to the pot in a single layer. Season with salt and pepper.
Cook the beef for 3-4 minutes on each side, then remove the beef and juices from the pan and set them aside until needed.
Add another tablespoon of olive oil to the same pot the beef was cooked in over medium-high heat. Then add the carrots, celery, and onion to the pot and cook for 3-4 minutes.
Add the garlic and tomato paste to the cooked vegetables and mix well. Cook for 1-2 minutes.
Add the red wine to the pot to deglaze the pan. Remove the pot from the heat and use a large spoon to scrape all the browned bits that have stuck to the bottom of the pan.
Add the beef broth, Worcestershire sauce, bay leaf, and thyme to the pot along with the cooked beef.
Bring the mixture to a light boil, then reduce the temperature to low heat. Let the soup simmer for 1 hour, stirring occasionally. *Skim any excess fat off the top of the soup.
Add the barley to the soup and continue to simmer the soup for another 45-60 minutes.*As the soup simmers the broth will reduce and you'll need to add water to the soup towards the end of the simmer. I added another 1 ½ cups of water to the soup to get the consistency right.
Add the chopped parsley to the soup and stir together. Taste and reseason as needed with salt and black pepper.
Serve the soup with crusty bread, and enjoy.
