Preheat oven to 425°. Generously season steak with salt and pepper. Heat 1 tablespoon oil in a large skillet over medium-high. Add steak and sear to brown on one side, 3 minutes. Transfer browned steak (browned-side up) to a large rimmed baking sheet. (Reserve skillet.) Toss asparagus with 1 tablespoon oil on other side of the pan and roast until steak is cooked to medium-rare, 15 to 17 minutes. Remove steak to a cutting board to rest.
While steak and asparagus roast, return reserved skillet to stove over medium. Heat remaining oil, then add shallot. Cook until shallot is tender, 2 minutes. Add wine and peppercorns and cook until wine has reduced by half, 2 minutes. Remove pan from heat and swirl in butter. Stir in parsley before serving. Slice meat and spoon sauce over steak; serve with asparagus.
Before her diagnosis, Caroline wrote a book on cakes called Cake Magic!. She started developing a birthday cake using her gluten-free mix found in that book. Check out other recipes she’s developing for her new life—and the stories behind them—on her blog, The Wright Recipes. Her next book, Soup Club, is a collection of recipes she made for her underground soup club of vegan and grain-free soups she delivers every week to friends throughout Seattle's rainy winter. (Available February 2021.)