Put cubed stew meat in a large pot. Add just enough water to cover the meat completely. Season with salt and pepper and chili flakes. Bring to boil, turn down the heat to medium-low, and simmer for about 45-60 mins with the lid partially on, until meat is tender. Turn down the heat if the water over boils.
Add in chopped squash, potatoes, parsnips, and carrots. Add more water if it doesn’t cover all the veggies. Bring to boil, reduce heat to a simmer and let it stew for 30 minutes.
In a small skillet on medium-high heat, saute in some olive oil the diced celery stalk and onion. When they soften, add in the tablespoon of tomato paste and 1/4 cup red wine. Add in the dried herbs. Stir everything together to make a nice mixture.
Add the mixture to the stew and give everything a good stir.