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.
[p.s.]
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."
[1]: https://en.wikipedia.org/wiki/Attar_of_Nishapur
[2]: "Expression-Logic of the Birds" aka "Conference of the Birds" https://en.wikipedia.org/wiki/The_Conference_of_the_Birds
Maybe instead of needing to be more enlightened, I just need a nap?
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".