Getting dog to go outside by himself

Question
We are the last house on a dead end dirt road with lots of land and would like our new dog to go outside by himself sometimes - particularly in the morning when we'd like to sleep in.  He is a border collie, 4 1/2 months old.  When we put him out he stands at the window and whimpers.  He does this for over 1/2 hour.  How do we get him to be comfortable being outside by himself?  He loves being outdoors, just likes us there too.

Answer
Pat, I hope you don't take offense to this, but I don't care how much land you have or whether you live on a dead-end road or not, it's extremely irresponsible (and lazy) to put your dog outside and leave him unattended. A 4-1/2 month old puppy shouldn't be outside alone anyway. Is there a specific reason you want him to be outside while you're sleeping in? Why can you not take him out to potty and then come back in and go back to bed (that's what I do, with all 4 of my dogs)? Dogs are pack animals, and want to be with their families; that is one reason he whines and whimpers when you put him outside and go back in the house.

I would recommend that you build him a kennel, or fence off around your house so that he will be confined if you want to put him outside and not watch him. I do not believe in tying dogs up, or chaining them, because this can cause all kinds of behavioral issues.