People often ask me, "Why did Buddha have to be such a downer? Obviously nirvana is a happy, cheerful state. So why didn't he just call it 'bliss' or something? Why did he have to label the reality he discovered with negative words like 'voidness,' 'emptiness,' and 'selflessness'?" When people respond negatively to these terms, it's often because they're worried that the words imply they are going to die, disappear, or go crazy in their attempts to seek enlightenment. And that's exactly why the Buddha called reality by those names. He did it on purpose, to liberate you! Why? Because the only thing that's frightened by the word "selflessness" is the artificially constructed, unreal, pretend self. It doesn't really exist. That pseudo-self seems to quiver and quake because the habit that makes it seem real wants to keep its hold on you. So if you're seeking happiness and freedom, then you should want to scare the heck out of your "self" -- you want to scare it right out of your head!
Actually, it is constantly scaring the heck out of you. Your "self" is always busy terrorizing you. You have a terrorist in your own brain, coming out of your own instincts and culture, who is pestering you all the time. "Don't relax too much," it is saying, "you'll get stepped on. A bug will bite you. Someone will be nasty to you. You'll get passed by, abused, sick. Don't be honest. Pretend. Because if you're honest, they'll hurt you." And it's ordering you, "Be my slave. Do what I tell you to do. Keep me installed up here at this very superficial level of the brain where I sit in my weird Woody Allen-type cockpit. Because I'm in control." Your falsely perceived, fixated, domineering self is precisely what's getting between you and a fulfilling life.
"Realizing your selflessness" does not mean that you become a nobody, it means that you become the type of somebody who is a viable, useful somebody, not a rigid, fixated, I'm-the-center-of-the-universe, isolated-from-others somebody. You become the type of somebody who is over the idea of a conceptually fixated and self-created "self," a pseudo-self. You become the type of somebody who is content never to be quite that sure of who you are - always free to be someone new, somebody more.
That's the whole point of selflessness. If you don't know exactly who you are all the time, you're not sick, you're actually in luck, because you're more realistic, more free, and more awake! You're being too intelligent to be stuck inside some frozen mask of personality! You've opened up your wisdom, and you've realized that "knowing who you are" is the trap - an impossible self-objectification. None of us knows who we really are. Facing that and then becoming all that we can be - astonishing, surprising, amazing - always fresh and new, always free to be more, brave enough to become a work in progress, choosing happiness, open-mindedness, and love over certitude, rigidity, and fear - this is realizing selflessness!