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Heat olive oil over medium heat in large skillet. Add garlic and sauté 20 seconds. Add broccoli, portobellos, and ¼ teaspoon sea salt and reduce heat to medium low. Cook, turning occasionally, until broccoli is completely tender and melting. Add a little more olive oil during process if it seems advisable.
Add sausage to pan and continue to sauté, breaking it up until meat is cooked through.
Divide between two bowls. Sprinkle with flaky sea salt, freshly ground black pepper, and chili flakes, if desired.