The knowing he is talking about here is mental or “mind” knowing.

The mind is actually a very limited tool, but because we often “identify” with it (meaning we think we are our minds and that voice in our head,) we come to depend on it far too much. There are 2 reasons he & I say it is a very limited tool:

• The intellect can only know things through subject-object - “I” (subject) know this (object.) There’s a whole realm of knowing and Consciousness beyond subject-object, a realm of knowing by becoming egoless or by total absorption, that is unavailable to mind.
• All mind’s knowing and recall is based on it’s main job, which is to survive the ego. It believes the body-mind-ego is a “separate individual,” separate from Consciousness, that was born and will die. This is an illusion which cannot be grasped by the mind, so in the meantime, the mind just does it’s job (and does it very well,) of protecting the ego and surviving it into “the future” (“time” is also an illusion.) But once again, that keeps it very limited in scope.

To be comfortable with not knowing means to hear the mind say whatever it says, whatever it thinks it knows (always based on the past,) and then stay open to feeling “I don’t need to rely on my mind’s past conclusions, I don’t need to know what’s going to happen next. That’s just my mind’s control & survival trip. If I stop putting so much emphasis on mental knowing, I can be free to allow the adventure of life to unfold in unforeseen, miraculous ways, instead of just playing a pre-recorded tape from the past every day.’

Control is an illusion anyway. Consciousness just unfolds however it does, and our minds have no idea what’s going to happen next or what to do about it. Might as well let go and surrender to the wonder of discovery, that can only occur when we don’t know, when we stop thinking we know something.

BIG “tip” here: The greatest single impediment to enlightenment is thinking we already know what enlightenment is and how it “happens” to a “person.” No kidding! The minute you stop believing your mind knows anything about enlightenment, you are 99% closer to enlightenment than you ever were before!

A frequent declaration you’ll hear from truly enlightened beings is, “Before enlightenment, I knew so much. Now I’m enlightened, I know nothing.”

Trust me, that’s not just a nice, poetic saying, it is totally the Reality.

Be comfortable with not knowing. Let go!