I have spent years as a lead which is the equivilancy as a manager, I have had to hire and fire people before. It is never easy and it doesn't get easier.

Everyone does have a valid point though and you have to look at it through their point of view, it helps. You weren't the one that put the bottle to his lips. More then likely this is not the first time it has happened. He just happened to be on your end of the world when it came to be.

Now a killer is when you actually have to lay people off. Thats when being a boss sucks. Imagine walking up to someone and saying "Sorry, the company isn't doing so well and your services are no longer needed." and they look at you with either the "what did I do wrong" look or the "I thought we where friends" look.

Try sleeping that night knowing you just put a good employee out on the streets and ****ed up their whole life and they didn't do anything wrong.