Do any of you have ideas on how to train a dog to be okay with being outside by himself? For context, our dog is generally very well-trained and has no separation anxiety when we leave the house. He's crate-trained but we don't even use it during the day because he just sleeps on his pet bed all day. However, when we're home, he wants to constantly be at someone's side. When we let him go outside, he'll run out there if he REALLY has to go, but usually he'll take a few steps out and then stop and turn around to make sure someone is coming with him. It's pretty annoying to have to go outside with him when it's cold or raining but we've at least gotten him to go out if one of us stands in the doorway.
He's a very social dog so as a general rule we don't leave him alone for long periods of time other than for work, but it'd be nice to be able to leave him out on a nice day if it's going to be 9 or 10 hours and him be ok with it. cont in comments...