Breaking up isn't easy and never will be easy but I think there are definitely ways to make a break up go more smoothly and thus not hurt yourself or the other person anymore that you have too.
First of all make sure it's the decision you want to make and you are ready to make it. Trying to leave a relationship that you are not quite done with makes for a messy, nasty ending that hurts you way more than necessary. For myself personally I knew in the back of my mind I was going to leave my boyfriend for almost a year before I was finally ready to let our relationship go.
Second, once you make the break you have to cut off all contact. NO EXCEPTIONS. After I left my ex we decided to "still be friends" and ended up talking more the next two days then we did in our relationship. There is no way you can grieve a relationship and move on if you are still talking with them and updating yourself on their life.
That means no calling, texting, facebooking, tweeting, IM'ing, skyping, smoke signaling whatever. You have to eliminate them from your life at least until all the major emotions are gone.
Third, resist the urge to bad mouth and put all your dirty laundry out there for the world. This should go without saying but we all know people that do it and have probably done it ourselves. Updated our status about how terrible they were or how crushed we are. This is not only immature but it just gives your ex reason to think you still care and a reason to talk to you. In the long run keeping all this drama to yourself will help you heal much better.
While no break up will ever be easy or painless not making it harder on yourself can make it much easier to get over the relationship and move on with your life.