1. In a large pot, heat olive oil over medium heat. Add the Italian sausage and cook, breaking it apart with a spoon, until browned and cooked through, about 5-7 minutes. Transfer the sausage to a plate and set aside.
2. In the same pot, add the diced onion and garlic, sautéing until the onion is translucent and the garlic is fragrant, about 3 minutes. My abuela always said this step sets the foundation for the entire dish, so take your time here.
3. Add the oregano, basil, and red pepper flakes, stirring to combine. Cook for an additional minute to let the spices bloom.
4. Pour in the diced tomatoes and chicken broth. Bring the mixture to a boil, then reduce the heat and let it simmer uncovered for 10 minutes.
5. Return the sausage to the pot, along with the chopped kale. Simmer for another 5 minutes, until the kale is wilted and tender.
6. Stir in the heavy cream and Parmesan cheese, allowing them to melt into the soup. Season with salt and pepper to taste. Cook for an additional 5 minutes, stirring occasionally.
7. Serve hot with crusty bread, if desired. The bread is perfect for soaking up every last bit of the creamy broth.

Remember, cooking is about joy and intuition—trust your senses, and feel free to adjust as you go!