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It's not really that bad IMO. Just say that you want to cancel and when the retention people ask why tell them the service costs too much and you think you can do better elsewhere. No need to be combative, these negotiations are what the people on the other end do all day every day. They will tell you what they can offer, you decide if it's worth it. You can even straight up tell them what you want and they will say whether or not they can do it. Even if they call your bluff you can always call back right afterwards and say you changed your mind and they will probably take you back. There's really no need for it to be uncomfortable, it really is their job and as soon as they hang up with you they are going to be talking to somebody else that is canceling. I can't speak for all companies but this has been my experience with DirecTV and Comcast.