Heat 1 tablespoon olive oil in a saucepan over medium-high heat. Cook pork chops until no longer pink in the center, about 4 minutes per side. Cool until easily handled, about 5 minutes. Cut the pork into bite-sized cubes.
Heat remaining 1 tablespoon olive oil in the saucepan. Add cubed pork, calabaza squash, corn, onion, tomatoes, and garlic and cook until onion is transparent, about 5 minutes. Stir in tomato sauce, cumin, salt, pepper, and garlic powder. Pour in chicken stock and simmer, covered, until flavors are combined, about 2 hours. Stir occasionally and check periodically to see if more chicken stock is needed.