Heat olive oil in a large pot or Dutch oven over medium heat. Add the onions and cook for 2-3 minutes, or until just starting to soften. Add the finely chopped carrots and celery and sprinkle with a pinch of salt. Mix well to combine and cook, over medium heat, for 8-10 minutes, or until vegetables have softened. Add the minced garlic and mix well to combine. Continue to cook for 1 minute more.
Pour in the entire contents of 2 (14.5 ounce) cans diced tomatoes. Add the ground cumin, oregano, paprika, salt, and black pepper. Mix well to combine.
Add the rinsed and drained lentils plus 6-8 cups of water or vegetable broth. Mix well. Increase heat to high and bring to a low boil.
As the pot comes to a boil, use a knife to chop 5-7 chipotle chiles mixed in adobo sauce. Transfer to a small bowl and mix with 2 tablespoons of tomato paste.
Once the pot reaches a boil, reduce to low and add the chipotle chili and tomato paste mixture. Mix thoroughly to incorporate. Cover and simmer for 30 minutes, stirring occasionally. After 30 minutes, add the butternut squash and continue to cook for an additional 30-45 minutes, or until lentils are cooked and butternut squash is tender.
Approximately 10 minutes before serving, stir in the chopped kale and mix well to combine.
Remove from heat and garnish with sour cream, avocado, cilantro or hot sauce (or all of the above!).