JK, of course, is asking specifically about our Tom D and whether as an 'aging' architect-artist he will have anything new to offer or instead will merely bask in/repeat his best work of the past. To me, few of the examples provided so far suggest that the latter is anything but inevitable. As JK points out, Newman didn't win an Oscar for The Hustler (which he should have), he won it for The Colour of Money (which he shouldn't have). BUT:
FL Wright and Cohen and Jefferson and Picasso and Newman etc etc all had this in common -- they'd grown *comfortable*: comfortable financially, comfortable with their place in the world/acclaim, and most importantly comfortable in their own skins.
I don't know him, but my guess is that our Tom D is *not* comfortable, and indeed is probably made *uncomfortable* at the very hint of being comfortable.
My guess is that this will make all the difference. The work/courses will keep evolving.
Signed
Dr Katz's Student