The first question:
Why do I want to wake up when, as you say, awakening only happens when I am not? This seems very paradoxical.
The ego is not your real self; the ego is a false entity, arbitrary. It is the ego that is your sleep, that surrounds you like a darkness, like a cloud. Hidden behind this darkness is your real self, your real being, which wants to wake up, which wants to get out of all this smoke, out of all this darkness, which wants to get out of the prison of the ego.
There is really no paradox, it only appears so. It appears paradoxical. Your question seems relevant…but you have two selves. One is the real: the one that you were born with, the one that was even before your birth, the one that will be there even when death has happened, the one that is running underneath like a hidden current. And the other is created by you, by your family, by your church, by your society, by your state, by the crowd.
This false one is a pretender: it pretends to be the real self. And the real self wants to come out of this unreal one surrounding it. It is a constant suffering for the real self because the real is being suffocated by the unreal; the real feels imprisoned in a dark cell. The real self is vast and has become confined in a very small space. It is crippling and paralyzing.
So when I say awakening happens only when you are not, I mean when your false ego is no more. And that is the only “I” you are aware of right now – that is the “I” you are identified with. Hence I say whatsoever you know of yourself will not be there when awakening happens. That does not mean you will not be there. You will be there, but that “you” will be so new, so utterly discontinuous with this “you” that you are living right now, that it is better not to mention it at all.
Hence Buddha is silent about it. Not only that: if you insist, he calls your real self anatta, a no-self, for the simple reason that to call it also a self may be confusing. The false is known as the self; if the real is also called a self, you may get confused. You are already too much confused. Buddha calls it a no-self.
But don’t lose heart. Don’t be worried, don’t be afraid that you will die completely. As you are, you will not be there, but you will be there as you should be. Your natural, your spontaneous being will be there.