About 4 years ago, I found myself at the lowest point of my life. A chronic health issue had left me bedridden and I finally gave up, knowing that I could not handle it by myself any longer. I started looking for people who could guide me out of the abyss.
I had been meditating for at least 10 years at this point. I was an autodidact, self-taught. I had done maybe 5 or 6 ten-day meditation retreats. I had significant experience with meditation yet still I was stuck in a way that I could not see an exit.
So I thought I would find someone who was more experienced than me to show me a way out. I found someone on Quora who kept on answering my questions with seemingly solid historical answers about traditional forms of meditation.
Previous to this, I thought enlightenment was a myth. I didn't really pay it much attention as I was heavily indoctrinated into a materialist framework.

My first paid session with this new mentor, he drops non chalantly that he had attained enlightenment and moves on quickly.
I did not move on quickly. I was put in somewhat of a crisis of faith for my materialist framework.

How was I supposed to evaluate this claim? What did it mean? Was he using this enlightenment in a con to get me to fork over more money?
He definitely seemed out of the ordinary, but my gut said something was up. I started researching this thing called enlightenment to find out how one can you evaluate claims of enlightenment. I ended up discontinuing our sessions. Here is what I learned:
You cannot evaluate someone's claim to enlightenment in the same way you can't really be sure whether someone you are talking to is lying to you or not (without damning evidence).

What is enlightenment?
Before attempting to answer that question, I would like to make it clear that I do not consider myself enlightened so I'm the wrong person to be answering this question, but due to my unique situation I had to find intellectual and gut answers to this question.
Enlightenment is when the ego is snuffed out and all one is left with is a non-dual perception of reality, i.e. there is no "I" that can be identified with. The Buddhists call this no-self, the Vedanta's call it Self. It doesn't matter what you call it. Either way there is no You
When I say the ego, I'm not talking about the Freudian ego. I'm talking about the Sanskrit term "Ahamkara" or the "I-maker". This arises when an object is perceived by the subject. An "I" is created, which follows the breath. I follow my breath.
The ego is the thing that is reading these words, but it is also the thing that is creating this unitary field of perception with all the thoughts and emotions in the moment. Other words for it: psyche, mind. Your ego is dominating your experience right now, fully. So is mine.
To get a sense of this, ask yourself the question:

Who am I?

What is this I if not what I think it is?

Notice what happens.

Now focus in on a perception, for example, the breath. Ask yourself what just focused its awareness on the breath? You can keep on going, every instant.
If you really pay attention, there is no verbal or conceptual thing you can point to that answers that question. This takes us back to the No-self/Self thing. Whatever is behind this feeling of I cannot be grasped by the mind. It is purely experiential. Try it yourself.
Now that we have a vague intellectual idea of what Enlightenment is (while being very far from the experience of it, if such a state exists), let's go into evaluating teachers who claim to have it.
There are two schools of thought that pertain to why a teacher would find it necessary to claim enlightenment. I will cover the one that I ran into first with my teacher who claimed it. His thinking is that, a student needs to know that it exists in order to pursue it.
In this sense, the state of enlightenment is talked of as an utterly normal state of being that is achievable so that students can focus on it, desire it above all else. If there is no enlightenment then a student is left without an aim for their practice. No aim = No achievement
The problem with this is that I get the sense that there are quite a few premature claims to enlightenment and a lot of incentives for spiritually minded folk to imagine they are enlightened (after experiencing cosmic bliss) and make a living from then on, building it all up.
Here is a great quote (1319) about this from a book that has been very helpful for me recently (DM if you want the name).

From this book and Jed Mckenna's book it seems that the enlightenment state is far different than even the most famous spiritual gurus claim.
That's another interesting thing that I have found. All the gurus (including Jed Mckenna) talk shit about the other gurus, calling them charlatans. J. Krishnamurti did it. U.G. Krishnamurti talked shit about J. Krishnamurti. All of them do it!
This leads me to the 2nd school of thought on claims to enlightenment.

It just confuses things.

There is no need to mention it because everyone has these pre-conceived notions of what it means (as I just displayed). Leave the whole thing alone and focus on what is real.
After I stopped working with my first mentor, I tried to find someone who did not mention enlightenment at all, yet still obviously had something (or maybe nothing) that I did not have access to, who was in some way more advanced than I (for lack of a better descriptor).
I ended up finding Jonathan Harrison who wrote a book called "Ending Stress". He never mentions enlightenment, meditation, spirituality, gurus, breathing, yoga, or any of the other usual suspects

Here is a tweet where I describe one of our lessons: https://twitter.com/StewartalsopIII/status/1300474798473003009
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