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Heat the olive oil in a large Dutch oven or saucepan over medium heat. Add the squash, leek, and celery and cook, stirring occasionally, until the vegetables start to soften, 10 minutes.
Stir in the garlic and sage, and cook until fragrant, 1 minute, then add adding the barley followed by the vegetable stock. Bring up to a gentle boil and cook, stirring occasionally, until the barley is al dente, 30 minutes. Add a splash of water if it gets too dry.
Stir in the grated Parmesan, followed by the greens. Cook until the greens are just wilted, about 3 to 4 minutes. Season to taste.
Serve with some crispy sage leaves and pumpkin seeds (if desired). Heat a splash of olive oil in a frying pan over medium-high heat, then drop in the sage leaves and pumpkin seeds and fry until crisp, 1 minute. You can also serve with Parmesan shavings and lemon zest.