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Make dressing. Mix all dressing ingredients together in shaker bottle or small bowl. Set aside until ready to use.
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Cook steak. Pat steak dry and season with salt and pepper. Heat oil in a large cast iron skillet over medium-high heat. Once hot, cook steak for 5 minutes. Flip and turn heat down to medium. Cook 5 more minutes. Remove to a cutting board and tent loosely with aluminum foil. Let rest 10 minutes. While steak is resting, continue to next step.
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In a large bowl, gently mix together salad greens, mushrooms, radishes, cherries, blueberries, and pumpkin seeds. If you are serving the salad immediately, you can also toss the dressing in with the salad in this step. If you will be eating some of the salad as leftovers, wait until you’re going to eat it to dress it.
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Slice steak into thin strips. Divide salad between serving plates and top with steak. Serve with fresh cracked pepper on top if desired.