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Set the Oven: Preheat oven to 400 °F.
Prepare the Chicken: Butterfly the chicken breast on a cutting board, pound it out with a meat mallet, dry it with a paper towel, season with salt and pepper, and set aside.
Prepare the Wet Rub: Combine olive oil, maple syrup, Italian herb seasoning, cayenne pepper, cinnamon powder, salt, and ground black pepper in a large mixing bowl.
Roast the Squash & Pecans: Set up a sheet pan and a small tray with parchment paper. Then, toss the acorn squash and pecans in the maple syrup sauce, dripping off any excess, and place the squash on the sheet pan; place in the oven and roast for 20 minutes.
Next, grease up a small cooking tray or use parchment paper. Then, remove the pecans dripping off any excess, place them on the tray, and set aside. While the squash roast, sear the chicken.
Cook the Chicken: Heat a frying pan with oil on medium-high heat. When the oil almost reaches the smoking point, place and sear the chicken breasts on both sides for at least 2 to 3 minutes each.
Coat the Chicken: Place the cooked chicken in the maple syrup mixture. Then, coat all the chicken in the syrup mixture and set aside.
Roast the Nuts: After the initial 20 minutes for the acorn squash, place the pecans in the oven and roast both for another 5 minutes. Then, remove and set aside.
Serve: Place the chicken breast on one side in the center of the plate. Then, In the same large bowl, make the dressing by whisking in the apple cider vinegar, cranberry sauce, and whole-grain Dijon mustard.
Reserve half the dressing for later. Add the mixed greens, pecans, and cranberries to the large bowl with the remaining dressing and combine well.
Plate up and alternate the mixed green salad and acorn squash on the other side of the plate's center. Then, top with goat cheese crumbles and drizzle the reserved dressing around the plate.