Heat 1 tablespoon olive oil in a saucepan over medium-high heat. Add pork chops; cook until no longer pink in center, about 4 minutes per side. Cool until easy to handle, about 5 minutes; cut into bite-sized cubes.

Heat remaining 1 tablespoon olive oil in the same saucepan. Add cubed pork, calabaza squash, corn, onion, tomatoes, and garlic; cook until onion translucent, about 5 minutes. Stir in tomato sauce, cumin, salt, pepper, and garlic powder; stir in chicken stock and simmer, covered, until flavors combined, about 2 hours, stirring and checking periodically to see if more stock needed.