Why are there so many different interpretations to enlightenment?

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There are no, strictly speaking, interpretations to enlightenment. It’s impossible. Enlightenment is the cessation of dreaming, and there is nothing that can be said about a mind that isn’t dreaming. What can I say? Here’s a rock, here’s a tree, here’s a bird. Enlightenment.

There is literally nothing that can be said about enlightenment which isn’t obvious to everyone already, because we all share the same underlying reality, we just all have different dreams.

But there are multiple, various, different interpretations of one’s prior dreams, so when anyone is talking about enlightenment, they are necessarily describing their prior dreams. It’s a necessarily comparative description of what they thought truth was (their prior falsehoods) and how it was abandoned. In most cases, people who think they’re enlightened are still dreaming on some level, so they love to describe their current, superior dream, also. For example, “I am loving awareness” or “I am infinite stillness”. In true enlightenment, you’re just a dude/gal who accepted reality for what it is, fully.

Every description of experience is also necessarily comparative. I can talk about how my body feels, ecstasy, beauty, emptiness, but it’s all comparative descriptions based on how it used to be before. Only ugliness can remember beauty, only hatred can remember love, and emptiness and fullness are also one and the same. In true enlightenment, all of this is forgotten including the distinction between divinity and mundanity and only the very real, mundane, everyday life remains.

Every sage approaches the topic from their prior experience with their dreaming, and the difference the cessation of dreaming has made on their direct experience of life, based on how they remember it. Hence the variety. Every sage must be able to describe their enlightenment in their own words, not the words of their lineage, otherwise they are not a sage but a parrot.

Truly great masters, such as Osho, go to great lengths to study different traditions (yoga, tantra, Buddhism, Hinduism, Tao etc.), but not to learn something from them for themselves. No true enlightened master has anything to learn from spirituality. They do so to learn about different systems of beliefs (different dreams), as well as different schools of practice, in order to be able to advise the students within their specific school of thought and ultimately help them destroy these beliefs when they have served their purpose. Osho went as far as studying western psychology and philosophy for precisely the same reason. He was fluent in all of that, not because it was important knowledge for his own realization, it was not, but simply to be efficient at his job.

Some masters insist that you adopt their terminology and their prior belief structure (ego, soul, the absolute, Buddhist descriptions, what have you) before they can teach you. Those are not very good masters. A good master must be able to help you destroy your own belief structures, not add something on top of it, even if the ultimate goal is to destroy it all. A good master also possesses complete flexibility of language, because they are interested in the substance of what you say rather than incessantly correcting your vocabulary.

Every fully enlightened being understands every description of enlightenment from every perspective. But before enlightenment, it’s impossible to understand it from any perspective.

Whenever a true master speaks to you in the context of enlightenment, they speak about your dreaming, not about their enlightenment. Outside of the context of enlightenment, they’re just an ordinary human being.