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Heat a 10-inch skillet over medium heat. Add barley; cook and stir 1 to 2 minutes or until toasted. Stir in stock (or broth) and squash; bring to a boil. Reduce heat. Cover; simmer 30 minutes, stirring occasionally. Uncover; boil 15 minutes more or until squash and barley are tender and most of the liquid is absorbed (mixture should still appear creamy). Remove from heat. Stir in basil and oregano.
Meanwhile, place garlic, salt and pepper on a cutting board. Using the flat side of a large knife, smash the garlic. Drag the flat side of the knife across the garlic in one direction then the opposite direction until a smooth paste forms. Place paste in a small bowl with 1 teaspoon oil; set aside. Slice pork to 1/4 to 1/2-inch thick; flatten slices with the palm of your hand. Rub garlic mixture over pork slices.
In a 12-inch skillet heat remaining 1 teaspoon oil over medium-high heat. Add pork; cook 1 to 2 minutes per side or until browned. Serve pork with barley mixture. Sprinkle with additional fresh herbs.