In a large Dutch Oven or pot, over medium-high heat, heat the oil. Add the bacon and cook until cooked through, about 4-5 minutes. Remove with a slotted spoon and reserve.
Season the beef generously with salt and pepper. Working in batches so not to overcrowd the pot, brown the beef pieces on all sides, about 1-2 min per side. Remove and reserve with the bacon.
Turn the heat down to medium. If necessary, add a little more oil. Stir in the onions and sauté until beginning to brown, about 5 minutes. Add the garlic and cook until fragrant.
Stir in the flour and tomato paste, mixing until well combined. Cook for a minute or two, until the paste turns a dark red color. Then, pour in the beef broth, using a wooden spoon to scrape all the browned bits from the bottom of the pot.
Stir in the beef broth, brown sugar, Worcestershire sauce, and a pinch of salt and pepper. Add the beef and bacon back into the pot, plus the thyme sprigs. Bring to a boil.
Once boiling, cover and lower the heat to a simmer. Cook for 1 hour.
Add the carrots and potatoes. Cover and continue cooking until the beef is falling-apart tender and the veggies are cooked, about 1 more hour.
If by this point, the stew is not thickened to your desired consistency, raise the heat to medium-high and bring to a boil. Let it cook uncovered until thickened; you can also add a slurry of equal parts flour and cold liquid (water or broth) to thicken further.
Discard thyme sprigs and taste for seasoning; adjust salt and pepper if necessary.
Stir in chopped parsley before serving!