The Sufi master Attar [1] wrote an entire book [2] -- using the symbol of "flyers" or "birds" -- describing the stages of seekers' path to enlightenment. The mataphor used was 'seven valleys of love' [3] encountered on the way to the 'King of the Birds', each with their own distinct psyho-spiritual state and requirements.
The journey has stages but for some there is a 'successful' end.
"If he who sets out on this way will not engage himself wholly and completely he will never be free from the sadness and melancholy which weigh him down."
An alternative perspective is that "meta-okayness" might be a goal to aim for. Can I be fundamentally OK even when I don't feel OK? Could I be OK with depression? Could I be OK with sadness? Could I be OK with being human?
Maybe instead of needing to be more enlightened, I just need a nap?
On a personal level "to thine own self be true". Definitely.
But if you are "depressed", "sad", and "don't feel OK" and rather take a "nap" instead of striving for enlightenment, you shouldn't go around giving talks on spiritual matters as a "teacher".
One thing is for sure, his images in old age (at least to me) convey a melancholic doubt as opposed to the expected beatific enlightened soul. YMMV.