That is a very interesting question. I would say yes, the dreamer must be awake during the dream (aka, lucid) in order for the transcendental moment to occur.
This is because, as you already noted,
nothing is unusual or beyond comprehension
during a NLD. You could be skateboarding on Saturn's rings with choirs of angels cheering you on and it will all seem perfectly normal, because "You," with the tools of memory and self-awareness in hand, are not present to confirm that this is not the way reality is supposed to look.
So transcendental moments could happen in NLD's (I personally believe they may happen all the time, BTW, and we just don't remember them as such, for the reason I just noted), but we don't recognize them as such during the dream. Instead, we remember them later and decide that they were something special... and yes, I would also say that we very often decide incorrectly, making all sorts of mystical magical attachments to a dream that was, well, just about skateboarding on a poorly conceived course. Now, the same problem exists -- where there is no metaphor, no filed memory, that can be used to properly describe the transcendent imagery -- but it is compounded by the fact that you are not "there" anymore, but are trying to remember where you were, and using memory as a tool for restoring the moment might just restore it incorrectly because, well, being a transcendent moment, your memory has no way of reproducing the imagery.
Of course, we may have an exception to this rule right on this thread... Slash mentioned above that he has non-lucid transcendent moments, and I believe him. But he has also, I believe, deeply trained his mind to be perceptive of such things, so, being properly prepared, he may be able to enjoy transcendent moments without the presence of his waking-life self-awareness, and his memory has something to hold onto until he wakes up to review the dream. That to me is incredibly impressive, but also incredibly rare (kudos to Slash, BTW!).
I think the best way to approach all this is by seeing it as utterly uncomplicated, with the obvious answers being the correct ones (as they often are with this stuff, regardless of the complex paths people take to describe them).
So yes, that self you are trying to let go of is a separate person from the world; that "separateness," or dual perspective, is the thing you need to shed in order to realize the presence of your true Self. Why? Simply because it gets in the way. Let's forget the pile of crap for a sec, and instead see that separateness as sort of a big wall that you've been building since childhood, with each brick being some unnecessary priority (i.e., appearance, persona's, possessions, judgements, fears, nostalgia, and much more). These bricks eventually become stacked so high that you lose track of the individual who first started the stacking, and see only the bricks. By the same process you've come to call the wall your true self, with your true Self -- and its presence in reality -- lost behind the bricks. And so, that constructed self becomes an outside observer of the world, always associ-- OMG, now
I'm spraying a word-firehose! Here, try this out:
We are built, biologically, to be brains sitting inside a skull, dependent on our senses to bring us the outside world. Because of this (and helped along by a certain natural solipsism that comes with that physical setup), we tend to see the world as a thing we are observing from a separate place, as though there is a world around us, and then also us. This is a dual perspective, meaning there is a "Me," and there is an "Everything else," and this duality is the default position for pretty much all of us. But self-awareness changes all that, and offers an opportunity to come to understand that we are not lone observers watching a world go by, but rather are participants in a constant state of interaction with reality... we are not alone in our skulls but
present, consciously, in the Thick of All Things.... and all this talk of "letting go," or "abandonment of ego," or whatever other happy cliches thoughtful types imagine, is simply nothing more than finding a way to step away from our natural dual perspective and into a much richer non-dual perspective.
In the end, DawnEyes, no matter what they say to complicate it, you aren't actually abandoning your Self, you are
reuniting with it, and the core "You" -- the one who put up all those bricks in the first place -- will always be there, memories, identity, and all; the difference is that that core You will no longer need to rely on those bricks to define who you are, or where you are -- you will simply be You, happily free to enjoy the Present without a load of crap weighing you down.
And on the same note:
I think the best way to learn about this stuff, oddly, is to keep your nose out of Buddhist magazines, which by their nature (in my opinion) tend to over-complicate everything, simply because they must keep on finding ways to say the same simple thing over and over again (sort of like all those books and sites on LD'ing, now that I think of it!
).
Based on what you wrote, for instance, I would find that teacher (or the student who may have misinterpreted his words) somewhat mistaken, because he has chosen to live without a sense of Self. Yes, it is an outstanding goal to live in the present, without
concern for the past or future, but to give yourself the delusion that there
was no past, or that it has been discarded, is to erase a lifetime of presence in the World, along with the wisdom that accompanies such presence (not to mention that the work involved in supporting such a delusion can be yet another delusion in itself). In a sense, the guy in the magazine is choosing to live not like an enlightened soul, but like a mindless drone... and yes, being a mindless drone can be a very comfortable existence (as the billions of mindless drones in this world would attest), but in the end that drone is missing out on the, yes, transcendental experience of mindfully participating in reality.
I'm not sure this is what you were asking, but it got me thinking:
Yes, by its nature a WILD (or DILD) is indeed a moment of transcendence, at least the first time it occurs. Since being awake (while you are asleep) in a dream is a completely new experience without reference points in memory or waking-life, a first-time lucid dream itself is a transcendental moment, if just a mild one. After that first time, the transcendence is done, because the dreamer has a basis of experience to draw on... well, it's done in terms of WILD and DILD transitions, but of course a whole universe of transcendental experience may still be in the offing...
WILD offers even more transcendental moments, I think, because its process brings you through all the various levels of falling asleep with your waking-life self-awareness and memory intact, so you get to experience as new things like HI, dreamlets, and REM atonia.
You can also tell that a first LD is a transcendental moment by the thousands of posts on these forums that start with something like "Was this a lucid dream?" or "What just happened to me," and entire forum sections are dedicated to dealing with -- often incorrectly -- all the
noise that accompanies a WILD dive; all of which illustrates the extreme newness of their experience.
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