Brown the meat. Add 2 tablespoons olive oil to a large stock pot or Dutch oven over medium-high heat. Add the sliced sausage, chicken pieces, and 1 tablespoon Cajun seasoning, salt, and pepper and sauté for 6-8 minutes. Stir occasionally to cook evenly and prevent burning. Transfer the chicken and sausage to a clean plate and set aside.
The "holy trinity". To the same pot over medium-low heat add the last tablespoon of olive oil. Stir in the minced onions, bell pepper, and celery, mixing well to combine. Sauté for 8-10 minutes, stirring frequently. Add the minced garlic, Cajun seasoning, salt, pepper, cayenne, Italian season, and red pepper flakes. and sauté for an additional minute.
Rice. Add the crushed tomatoes, Worcestershire sauce, white rice, and low-sodium chicken broth to the pot. Sit well to combine. Bring mixture to a simmer, then reduce heat to low, cover, and cook for approximately 25-30 minutes, or until the rice is nearly cooked through, stirring every 5 minutes to prevent the rice from burning and sticking to the bottom of the pot.
Add the shrimp and okra (optional). Stir in the shrimp and the sliced okra, mixing well to combine. Continue to cook on low, stirring frequently, until the shrimp are cooked, approximately 5 minutes. Add the chicken and sausage back to the pot and season with additional salt, pepper, and Cajun seasoning, if desired. Remove from heat.
Garnish. Serve warm garnished with chopped parsley and green onion if desired. Refrigerate leftovers in a sealed container for up to 4 days. Enjoy!