Add olive oil to a large Dutch oven and place over medium high heat for 1 minute. While the oil heats up, season the beef all over with ½ teaspoon of salt and ½ teaspoon of pepper. Once the oil is shimmering, add beef cubes. Cook for 10 minutes, stirring occasionally, or until the beef is seared all over. Remove from the Dutch oven with a slotted spoon and set aside.

Add onion, carrot and celery to the Dutch oven and season with remaining salt and pepper. Reduce heat to medium and cook, scraping up any brown bits that have formed on the bottom of the pan, for about 10 minutes, or until the vegetables start to soften.

Add Italian seasoning and Worcestershire sauce and stir well to coat all of the vegetables. Cook for 1 to 2 minutes, then add crushed tomatoes and stock, stirring to scrape up any more brown bits on the bottom of the pan.

Add beef to the Dutch oven and bring to a boil. Cover, reduce heat to a simmer and cook for 1 hour. After 1 hour, add pearled barley, cover again and cook for an additional 1 hour, or until both the beef and the barley are tender.