An awakening to selflessness is a shift in context from a sense of I to realized selflessness. The content can stay the same, and the context shifts.
This is similar to what Ken Wilber says on p. 115 in Integral Spirituality:
Enlightenment is becoming one with all states and all stages at any given time.
Context and content
The Ground of it all, of the seeing and the seen, context and content, emptiness and form, is inherently absent of any I, and this is what awakens to its own nature.
(Even the temporary sense of an I is inherently absent of any I. It may appear very real and substantial as long as it is there, but even in the midst of all that - and the drama that goes with it, it is inherently absent of any I.)
And the content includes the current unfolding of this universe and this particular human self. In other words, it includes the current evolutionary stage of the Universe and the human species, and the current developmental stage of this human self, just as KW points out in that quote.
Any expression is relative truth
Any expression of this is naturally in the realm of relative truths, and there is nothing absolute in any of the many ways to talk about or communicate this.
Words split the world, and what they point to is effortlessly beyond and includes all polarities.
Any map is different from the actual terrain. Even in its reflection of the terrain, it highlights some features and deemphasize and leave out other.
One with? Sort of.
So when Ken Wilber talks about this, that too is a relative - and incomplete, truth. Sometimes, there is more detail and accuracy in the way he talks about Big Mind awakening to itself. Other times, such as here, it is more casual and more inaccuracies creep in.
He says one with, but this indicates that there is something that is one with something else.
Here, Ground awakens to its own nature, absent of I anywhere. It is not one, not two, not not one, not not two. It is all of those and none of those. It is actually much simpler and more ordinary than what any words can reflect.
For practical purposes, speaking casually about it, one with is perfectly fine. At the same time, it does not quite capture it.
One with, not yet Ground awakening
It can even give a false impression of Ground awakening when there is none.
At some point, the center of gravity, our identity, shifts from a part of the seen (our human self) to the seeing itself. And there may then be the realization that the seen and the seeing are not so different from each other, not really two.
There is an intuition that they are aspects of a whole, expressions of the same Ground. And there is a sense of no separation, of being one with everything. But there is still a sense of I here, placed in the seeing.
This may appear to be close to Ground awakening, but it is not Ground awakening.
It is really as far from Ground awakening as an identification with the seen is from an identification with the seeing. Each of these three shifts are clear, unmistaken, and significant.
Ground awakening, simpler and more ordinary than words can capture
In Ground awakening, all of this - the seen and the seeing, emptiness and form, is revealed to be inherently absent of any I. There is not one, not two, not both, not neither.
Just what is, absent of any I. Simpler, and really more ordinary, than what any words or models can capture.