Preheat your oven to 400°F (200°C). Toss the cubed butternut squash in 1 tablespoon of olive oil, sprinkle salt and pepper over it, and lay it out on a baking sheet.

Place the baking sheet in the preheated oven and roast for about 25-30 minutes, or until tender and slightly golden.

While the squash is roasting, heat the remaining olive oil in a pan over medium-high heat. Season the steaks with salt, pepper, oregano, and thyme. Sear for 3-4 minutes per side, depending on your preferred doneness.

In the last minute of cooking the steaks, toss in the minced garlic and quickly sauté it until fragrant. Remove from heat and allow the steaks to rest.

Slice the steaks against the grain, layer in a bowl with roasted butternut squash, and add sliced steak on top, sprinkling with herbs if desired.