Brett (kilo) brings up a good point as well. The world is much more complicated (and thankfully so) than simply black and white answers to everything. Being given a whole area with thousands of different shades of gray gives life the complication it needs to be interesting. Granted, when you're trying to choose that perfect solution, it sucks, but ultimately you are the one who is going to have to live with it and deal with whatever consequences that occur. It's a part of life, no matter how you look at it.

There are two major things to remember though:
1. You can't please everyone; so don't even try it.

When I was breaking up with my ex for the first time, I tried to be really nice about it, telling her I still wanted to be her friend and that I still really cared for her and all this crap, but that I didn't want to be with her. Essentially, I was trying to make it easy for both parties. I thought I was letting her down easy, and at the same time keeping it relatively guilt and pain free for myself. Well, neither worked out well. I was on the phone for hours at a time dealing with everything from screaming to crying to promises. It could have easily ruined my summer had she not lived 200 miles away.

Foolishly we got back together for about a month, and then everything went to shit because I really wasn't in it. I was upfront with her at this point, and while it wasn't easy for her, it ultimately turned out a lot better for me in the end. So, even in trying to do the "right" thing, by being a good guy and letting her down easy, I was actually playing with her emotions, which led to me hearing shit on the phone. Moral of the story: do what suits YOU best. If your goal is X, then tell people that X is your goal.

2. Making a decision might suck, and people might get mad, but after all is said and done, those people who are your true friends will understand and will accept it and forgive. Those who don't can piss off.

I'd say the exception to this rule is during something menial, like a pickup sports game, and you know your best friend sucks, and you don't take him before last pick. That's just messed up.

Other than that, your true friends are people who should understand you well enough to know generally how you think and what's going on in their life. I've bailed on major plans with friends before because I've had to take care of family matters around my house. Granted they were not happy at all, because I promised and promised and did extra stuff to make sure my week would be free, but something came up and I wasn't going to leave my parents in a lurch, even though they could've probably handled it themselves. When I first told my friends, they were rightfully pissed, but I gave them the week or so to cool down and visited them as soon as they got back. They weren't mad at all; in fact, they were more concerned that everything was ok by me. Thankfully it was. Case in point, your real friends will understand a decision that you make can potentially hurt them, but as long as it's not done maliciously, and if they are your real friends, then I think they would understand where you're coming from, especially if you let them know what's going on in your life.