Place the cubed chuck in a mixing bowl, sprinkle with salt and black pepper, and toss until evenly seasoned. Set aside.
Heat a heavy-bottomed large pot over medium heat. Add the bacon and onion and cook for 5-6 minutes, or until the onions are softened.
Using a slotted spoon, transfer the onions and bacon pieces to a bowl and set aside.
Add the olive oil to the bacon grease in the pot and increase the heat to medium-high. Add the beef to the pot and brown all sides (this takes me about 4-6 minutes, but can differ depending on the size of the beef, heat of the stovetop, etc.). If needed, cook the beef in batches to prevent crowding.
If browning in batches, return all the beef to the pot and sprinkle with the flour. Add the onion and bacon to the pot, stir well, and cook for 2-3 minutes or until lightly golden.
Add the tomato paste and cook for 1-2 minutes, stirring well to coat the beef.
Stir in the Guinness and scrape up any browned bits from the bottom of the pot.
Add the beef broth, bay leaves, dried thyme, Worcestershire sauce, and half the carrots, and stir until well combined. Cook uncovered on medium-low for 1 ½ hours, stirring it occasionally.
Stir in the remaining carrots, celery, and potatoes. Cook uncovered over medium-low heat for another hour, until the carrots and potatoes are fork-tender.
Remove the bay leaves and season the stew to taste with salt and pepper. Enjoy hot over Colcannon or creamy mashed potatoes or with Irish soda bread.