1. Preheat oven to 400°F and line a baking sheet with parchment paper. Arrange bacon in a single layer and bake for 15-20 minutes, or until crispy. Remove from the oven and let cool. Once cooled, chop into large pieces.
2. In a large pan, heat olive oil over medium. Add the ground beef, season with the salt and pepper, and cook until browned. Remove from heat and set aside.
3. Assemble the bowls starting with a base of lettuce and top with ground beef, bacon, sliced red onion, cherry tomatoes, pickles, and shredded cheese. Drizzle each bowl with optional thousand island dressing and serve.