Season the chuck roast liberally with salt and pepper all over.
Heat a large Dutch oven, over high heat. Add one tablespoon of olive oil. Add the onion, carrots and potatoes and cook, stirring once or twice until the veggies are just slightly browned on the edges, about 5 minutes. Do not leave the veggies in there too long, you don't want them to become soft. Remove the veggies to a plate.
Add another drizzle of oil and once hot, add the chuck roast and sear all over, about 3-4 minutes per side. Remove the chuck roast from the pan.
Carefully pour in the wine and deglaze the pan, scraping up any brown bits off the bottom. Remove from the heat.
Add the meat back to the pan and cover with the beef broth, Worcestershire sauce, and the balsamic. Throw in the mushrooms and browned veggies, thyme, rosemary, cranberries, and honey.
Cover the pan and place in the oven. Roast for 3-4 hours or until the roast is cooked to your liking.