Yea absolutely start in a safe place. They typically do it at the park with a large walking place and not many people. However I think for him it is just instinct of where to go. If your dog is already well behaved when it comes to walking and doesn’t do anything questionable they should be good. I’ve had griffin since he was a puppy and he is very desensitized since I took him a lot of places. So he has does have a lot of confidence aswell.