Heat 1 tablespoon olive oil in a wide pot over medium-high. Add the Brussels sprouts, cut side down, and cook in an even layer for 3–5 minutes. Turn and continue cooking for 2–4 minutes to char them completely. Add a big pinch of salt and transfer the Brussels sprouts to a bowl.
Cook the squash and onion:
Add the remaining 1 tablespoon olive oil to the pot. Turn the heat to medium. Add the butternut squash and cook for 3–4 minutes until the edges turn golden brown. Add a pinch of salt.
Add the onion and cook an additional 5 minutes.
Cook the aromatics:
Add the sage, rosemary, and minced garlic. Toss to coat and cook for 1 minute until fragrant.
Simmer the sauce:
Add the maple syrup, vegetable stock, and a pinch of crushed red pepper. Bring to a boil. Reduce heat to low and simmer for 20–30 minutes or until the squash is tender and the broth reduces by half. If the liquid reduces too quickly, add a few splashes of broth or water periodically. Taste and add salt and pepper if needed. If you like a sweeter sauce, add another teaspoon of maple syrup.
Cook the orzo:
Bring a medium pot of salted water to a boil as the sauce simmers. Cook the orzo according to package instructions. Reserve ½ cup pasta water. Drain the orzo and set aside.
Finish the sauce:
Once the squash is tender, taste the sauce and season once more. Bring it back to a boil over medium-high heat.
Add the Brussels sprouts, orzo, and goat cheese to the sauce. Toss to combine, adding pasta cooking water as needed until the orzo is well-coated. Continue to cook for 1 minute until the cheese melts. Turn off the heat. Taste and season once more.
To serve:
Spoon the butternut squash orzo onto a serving platter. Finish with another sprinkle of goat cheese. Enjoy!