For penne pasta, cook pasta in salted water in a large pot until just al dente. Don't overcook pasta or it will fall apart in skillet later. Reserve one cup of pasta cooking water. Drain pasta when done and set aside. You can start the other ingredients while the pasta cooks.
In a large skillet over medium heat, add olive oil and Italian sausage. As sausage cooks, break it up in the skillet. Brown the sausage really well. It should cook for 8-10 minutes. Remove browned sausage from the skillet, leaving as much oil in the skillet as possible. Do not wipe out the skillet.
To prepare butternut squash, cut in half and scoop out and seeds. Then slice off ends of squash so it can firmly sit on a cutting board and slice down the sides, removing peel. Then dice squash into about 1/2-inch cubes.
Add squash to the skillet with the sausage drippings and oil. Add pasta water to the skillet and use the liquid to scrape up any bits. Cook until squash is browned, stirring occasionally, maybe 5-6 minutes. Then add shallot and garlic and continue to cook until squash is tender. If your pieces are larger and squash is still tough, you can add a little extra water and cover the skillet and let the squash steam for a few minutes.
Add drained pasta to the skillet along with cooked sausage and cream and toss to combine and allow to thicken slightly over low heat. If pasta is very dry, add more water by the half cup.
Season the pasta with salt and pepper and adjust to your liking.
Serve pasta immediately while warm garnished with parsley and grated gouda cheese.