What is the connection between enlightenment and non-duality?

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Enlightenment is a big, huge concept that can mean a lot of things.

Non-duality is a somewhat smaller, but still huge concept, that is also hard to define.

Both terms are generally associated with Buddhism, but both terms predate it. The word ‘non-duality’ stems from the Sanskrit Advaita, which generally means ‘without a second’.

It needs to be stressed that the attempt to give meaning to these concepts is a religious one. Meaning you’re making statements about what people should believe in and do. To give you an idea of the unholy bog we’re playing in:

Bodhi is a Theravada term. It literally means "awakening" and "understanding". Someone who is awakened has gained insight into the workings of the mind which keeps us imprisoned in craving, suffering and rebirth, and has also gained insight into the way that leads to nirvana, the liberation of oneself from this imprisonment.

Prajna is a Mahayana term. It refers to insight into our true nature, which according to Madhyamaka is empty of a personal essence in the stream of experience. But it also refers to the Tathāgata-garbha or Buddha-nature, the essential basic-consciousness beyond the stream of experience.

In Zen, kensho means "seeing into one's true nature".

Satori is often used interchangeably with kensho, but refers to the experience of kensho.

Source: Wikipedia

Is enlightenment knowledge? Is it an experience? Is it insight? Is it all of these? Each of those concepts has entire troops of monks who spent their entire lives studying and meditating on them, for thousands of years.

When Westerners use these terms, generally they apply their own cultural understandings to them, which all tend to stem from ancient Greek philosophy. We’re only barely aware of the religious history of the terms.

With the history out of the way, I can now deal with the common syncretic understanding of the two words. I have arrived at these definitions through reading and distilling lots of more recent spiritual authors who have had varying influences, both East and West. There is nothing any more ‘right’ about them, they just have the benefit of hindsight.

Enlightenment is a necessarily fuzzy word that can mean anything anybody wants it to mean. Non-duality refers to a specific way of being in which a person does not identify with body, mind, awareness, or will. Non-duality has been studied pretty thoroughly by many Buddhist traditions and we can create specific exercises and techniques, called dharma, to bring about that state.

You can dictate that the only real definition of enlightenment is non-duality, but be aware that not everybody thinks that way. Buddhism is an Iron Age religion and carries with it a lot of the same sort of scriptural baggage that the Old Testament has, stuff that served the peoples of thousands of years ago well but is just embarrassing now.