In a large skillet, cook the diced bacon over medium heat until crispy, about 5-7  minutes. Remove the bacon with a slotted spoon and drain on a plate lined with paper towels. Leave the bacon grease in the pan.

Add 1 tablespoon of olive oil to the skillet with the bacon grease and heat over medium heat. Place the the halved Brussels sprouts cut-side down in the pan. Do your best to make a single layer. Push overlapping sprouts out to the side of the pan.

Cook for 5 -7 minutes until the sprouts start to develop a golden-brown sear.

Season with salt and pepper. Move the golden brown sprouts to the outer edges of the pan and flip to brown on the other side. Shift the paler sprouts (cut side down) to the center of the pan to brown. Continue cooking for another 5 minutes. Hint: Add 1 tablespoon of oil if the pan looks dry.

Continue flipping and cooking the remaining Brussels sprouts for another 2-5 minutes until all the sprouts are tender, but still green and covered in crispy brown spots.

Once the sprouts are tender, remove the pan from the heat. Drizzle the maple syrup over the Brussels sprouts and toss to coat in the maple glaze.  

Transfer the maple-glazed Brussel sprouts to a serving dish and top with crispy bacon. Serve warm.