Preheat oven to 350 degrees F (180 degrees C).
Add 1 tablespoon of olive oil to a large stockpot or Dutch oven set over medium-high heat. Add the sliced sausage and cook for approximately 1 minute per side. Remove to a clean plate and set aside.
Add the chicken pieces to a large bowl and season with approximately 1 tablespoon of Cajun seasoning, salt, and pepper. Return the stockpot or Dutch oven (used to brown the sausage) to medium-high heat. Add 1 more tablespoon of olive oil and add the chicken. Cook, stirring occasionally, for 6-8 minutes, or until chicken is cooked. Transfer the chicken to a clean plate and set aside.
To the same pot set over medium-low heat add the last tablespoon of olive oil. Add in the minced onions, bell pepper, and celery, mixing well to combine. Cook for 8-10 minutes, or until softening, stirring frequently.
Add the minced garlic, Cajun seasoning, salt, pepper, cayenne, Italian season, and red pepper flakes. Mix well and continue to cook for an additional minute.
Mix in the crushed tomatoes, Worcestershire sauce, white rice, and low-sodium chicken broth with the softened veggies. Mix well to combine. Bring to a simmer, then reduce heat to low and cover with a tight-fitting lid
Cook for approximately 25-30 minutes, or until the rice is nearly cooked through, gently stirring every 5 minutes to prevent the rice from burning and sticking to the bottom of the pot (see note - how to cook your rice in the oven).
As the rice cooks, add 2 tablespoons of butter and sear the shrimp for 2 minutes on each side in a large skillet set over medium-high heat.
When the rice is nearly finished cooking, stir in the shrimp and the sliced okra, and return the chicken and sausage back to the pot. Gently mix to combine with the rice. Continue to cook on low, stirring as needed, until the shrimp is cooked, approximately 5-8 minutes.
Remove from heat. Serve warm garnished with chopped parsley and green onion if desired. Refrigerate leftovers in a sealed container for up to 4 days. Enjoy!