So my current boss is also a friend of mine.  I’ve known him for over 15 years before I even got my job with him.  I’ve been working my new job for just over a year and and he’s been the boss of the branch ever since it opened about two and a half years ago.  It all started out great.  Got great hours, decent pay, vacation.  But the entire time I’ve worked here, I only hear my boss complaining about how he doesn’t get paid enough, how he falls behind on the mounds of work that gets dropped on him, how he is getting a second job because he claims to not make enough money here (but I know he’s just an irresponsible spender and he makes plenty.)  It’s gotten really discouraging for me because I have intentions on moving up in the company but it just makes it so hard to hear him complaining.  I know his position isn’t as hard as he’s making it because I know he’s the kind of guy to try to make numerous short cuts that almost always end up backfiring on him and he’s also just a tad bit immature for his age.  I’ve wanted to say something to him.  But I just don’t know how to do it in a way that won’t offend him.  WIBTA if I told him to just keep all his problems to himself or should I just try to keep ignoring it?