Season the short ribs all over with salt and pepper then dust with flour. Heat a 7-quart Dutch oven over medium-high heat, add the olive oil and heat through. Working in batches, sear the ribs on all sides, about 5 minutes total. Remove to a plate and repeat with the remaining ribs.
Return the pot to medium heat and add the onion, celery and carrot, sautéing until tender, about 6 minutes. Stir in the tomato paste and thyme then add the garlic, bourbon, maple syrup and beef stock. Return the short ribs to the pot and bring to a boil over medium heat.
Cover the Dutch oven and move it to the oven and cook, turning the ribs occasionally, until the meat is fork tender, about 3 to 3½ hours.
For the caramelized shallot & black pepper mashed potatoes:
Heat a medium sauté pan over medium-low heat, add the oil and heat through. Add the shallots and cook, stirring frequently, until they are soft and pale brown, about 10 minutes. Set aside.
Rinse and peel the potatoes then cut into 1½” chunks. Add the potatoes to a large pot and cover with water. Bring water to a rolling boil and cook the potatoes until they are tender, stirring occasionally, about 20 minutes. Drain the potatoes completely.
Add the potatoes to a free standing mixer or a large bowl if using a handheld mixer. Depending on the size of the mixer the mashing may have to be done in batches. After potatoes are mashed, beat in the cream cheese, butter and shallots. Season with the salt and add the pepper.
To serve:
Serve the short ribs over mashed potatoes and sautéed kale (optional). Ladle the additional sauce over the top of the short ribs and serve.