Preheat oven to 350°. Place mushrooms in a food processor and pulse until evenly ground.
Heat 2 tbsp olive oil in a large skillet over medium heat. When hot add onions and garlic and cook briefly until fragrant. Add mushrooms, ½ tsp salt and ¼ tsp pepper. Cook, stirring occasionally, until mushrooms have given up moisture and onions are translucent, about 7-10 minutes.
While mushrooms are cooking, in a medium bowl mix together ground beef, egg, bread crumbs, Dijon, ½ tsp salt, and ¼ tsp pepper.
When mushroom mixture is done cooking, add to the ground beef mixture and mix everything together until evenly combined.
Grease a large sheet pan with nonstick spray. Place meat mixture on sheet pan and shape into a 8x4-inch loaf. Brush the top with ketchup.
In a medium bowl toss together Brussels sprouts with 1 tbsp olive oil, cumin , ½ tsp salt, and ¼ tsp pepper. Spread on sheet pan around meatloaf.
Bake for 30-40 minutes until meatloaf is at least 160° internal temperature and Brussels sprouts are browned and tender.
Meanwhile, heat a large pot of salted water over high heat. When boiling add potatoes and cook for 15-20 minutes until very tender. Drain and return to pot. Mash potatoes to desired consistency. Stir in butter, 1/4 cup of milk, ½ tsp salt, and ¼ tsp pepper. Add more milk as needed and adjust seasoning with salt and pepper to taste.
Allow meatloaf to rest for about 5 minutes before slicing and serving.