"I wish I had an answer to that because I'm tired of answering that question." --Yogi Berra
Enlightenment. It's why you practice, right? To become enlightened? You probably have your own ideas about it.
The end of suffering. The end of karma. The end of confusion. Free from the struggles of life. The end of anger or greed or stupidity. Free from neuroses and neurotic thinking. Ultimate sanity. Know what life is and what life is about. Emptiness. Free from subjective interpretation. See things just as they are. Free from bias and prejudice. Total objectivity. Infallible. Transform all experience into wisdom. Special powers. Complete and total moral integrity. Beyond reproach, beyond question in everything you do. Know exactly what to do in every situation and do it effortlessly. Able to help others out of their misery. Union of emptiness and compassion. Able to change the world, transform society, heal and cure all that is wrong with the world. The leading edge of the best hope for humanity.
It all sounds pretty wonderful.
Enlightenment is a promise of freedom from life as you know it. It's your ticket out of this mess called "life." It is something other than what you are experiencing right now. When you are enlightened, all your frustration and difficulties with practice and with life will vanish in the light of your understanding and wisdom.
Aren't you already enlightened, but just don't realize it? That's what some teachers say. It seems that if you don't know you are enlightened, then you aren't and if you do know you are then you are. You know you are, because you've heard that you are, but it doesn't seem to make any difference. Does that mean that you don't know that you are enlightened or you do? It's all a bit confusing, but you know it will all make sense once you are enlightened. Or is it when you know you are enlightened?
Right now, you can't wait. You work at practice, putting in time on your cushion, going to retreats. You become an "experienced practitioner." But nothing seems to change. You still get distracted when you meditate. You still react to situations unpredictably. You hear about these extraordinary experiences, non-self, emptiness, sheer clarity, bliss, etc. Maybe you taste them from time to time. But you are still stuck in life, and that can't be enlightenment. When you hear that so and so has experienced satori or kensho or become a stream-winner or has insight or seen the nature of mind -- whatever -- they seem to be the same person to you. You can't really say what is different. And you still have problems in your life. Most of the time you are struggling with the same old same old in your meditation.
You spend a lot of time with your teacher and you see that he or she isn't free from the problems of life. She is able to guide you in your practice, perhaps very well. His meditation instruction is precise and illuminating. But now and then, you get a glimpse, or more than a glimpse of what seems to be their own struggles with life. Maybe you see them acting inappropriately or even unethically in certain areas. How can that be? Aren't they beyond that? Aren't they realized? Aren't they enlightened?
You begin to wonder about the point of all this work. Have you been deceived? Have you fooled yourself? Where is this freedom that everyone talks about? Yet you continue to practice.
While you may not notice anything changing, something happens. You sometimes notice that situations and interactions that were problems for you are no longer problems, but you don't really remember when they stopped being problems. You aren't as hard on yourself, even though you pay much more attention to what you do, what you say, and how you direct your attention. There are long periods of barely discernible changes, and then something shifts profoundly, for no apparent reason.
You see that some problematic behaviors and ways of thinking have dropped away. Others, you realize, are probably not going to drop away, but you aren't taken in by them anymore. You are much more accepting of yourself and others. You see very clearly how reactions based on survival, getting emotional needs met or being somebody consistently result in suffering and struggle for yourself and those around you. You see this in yourself, and you see it in others. Because you see it so clearly in yourself, you know how it is for others, and your heart goes out to them, even when their behavior is infuriating.
The upshot is that you are a part of the unfolding of life, rather than apart from it. You know contentment, peace, freedom, understanding and compassion, but they are not anything like what you thought they would be. They don't seem special in anyway, and yet they are. You place less and less value on having certain experiences. It's more important for you just to be there and to do the best you can, in ordinary situations, and in difficult ones. You stop looking for something different. Life itself points a way and you take it.