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Heat the oil in a dutch oven over medium-high heat. Add the onion, carrot, 1 tsp salt, and ¼ tsp pepper and cook, stirring occasionally, about 5 minutes or until veggies are soft.
Pour in the water and bring to a boil.
Stir in the barley and bay leaf. Reduce heat to medium-low and simmer covered, about 20 minutes.
Stir in the potatoes and pickles, turn up the heat and return to a boil. Reduce heat to medium-low again, partially cover the dutch oven and continue simmering until barley and potatoes are cooked through, about 25 minutes.
Stir in the pickle brine and cook 5 more minutes. Add salt and pepper to taste.
Serve the soup hot garnished with fresh dill.