Interesting stuff, Bramble. I recall going over this again and again in Zen, where the paradox of goals presents itself. That is, that if you have enlightenment as a goal, you have a massive barrier right then and there. In fact, you could say that the idea of enlightenment is itself a barrier. But a barrier to what, I hear you cry. As I used to say to my best pal, who was a Sufi, what does it mean to try? Both of us would collapse in giggles at that, the laughter is really about not trying any more. I don't have to get it right.
It is interesting to look at it in terms of life trajectories. When I encountered Zen about 40 years ago, I was like a puppy with two tails, and ran around trying to convince everyone that they should be like me! I can laugh at that now. This is a kind of messianic phase, which hopefully wears off.
But advancing years have an interesting effect on all this. Partly I became less interested - it didn't seem to matter whether I was enlightened or not. Or nothing seemed to matter, in a good kind of way. It's hard to describe this. The idea of transcendence seems absurd to me now, but I would not condemn anyone who desires it.