Don't get me wrong, if you read Ted Nelson writing about Xanadu uncritically, you'll get a tale of utopia denied and genius tortured, but the reality seems much more prosaic.
Edit: I should also add that the web as originally built has real advantages over Xanadu. In order to implement its universal transclusion and DRM (yes, Xanadu had a scheme for DRM and micropayments to creators), Xanadu had to be centralized. I'd argue this is worse both socially and technologically. Adding DRM to the infrastructure of the web is something that I would really hate.
But I will say that Xanadu was conceptually not centralized; the peer-to-peer exchange of arbitrary information at scale was definitely part of the architecture. However, the major and systemic performance problems entirely prevented any scaling up of the system, which effectively means the distributed architecture was never proven.
I agree to a certain extent with the Chandler analogy, insofar as there was a lot of "architecture astronautics" that added complexity to the system beyond the ability of the team to manage -- especially given the limitations of early 1990s development machines.
One could refer to the article itself for Walker's own view of the sad outcome:
'Rather than push their product into the marketplace quickly, where it could compete, adapt, or die, the Xanadu programmers intended to produce their revolution ab initio.
'“When this process fails,” wrote Walker in his collection of documents from and about Autodesk, “and it always does, that doesn’t seem to weaken the belief in a design process which, in reality, is as bogus as astrology. It’s always a bad manager, problems with tools, etc.—precisely the unpredictable factors which make a priori design impossible in the first place.”'
He wasn't wrong. Xanadu tried to leap fully formed into the world as a megalithic architecture capable of arbitrarily large data structures supporting arbitrarily small comparisons and transclusions, and it couldn't compete with HTTP's fully open specification and implementations, low barrier to entry, and extreme simplicity.
Fallback positions from the idealized "roadmap" are what happens when VCs get involved with a system that offers that Zero To One advantage -- but you have to have a One to offer the VCs, which Memex didn't. The question then becomes how much of your road map can be recovered or, perhaps more to the point, do you even _want_ to recover in the light of ground truth experience? At present there is a lot of potential for Information Centric Networking that would be more likely realized in a Ship-Dumbed-Down-Decentralized-Xanadu1994 alternative universe than is likely to be realized now.
Why was Brendan Eich under such pressure from VCs to throw together a scripting language over a weekend?
https://www.youtube.com/watch?v=S0ZWtsYyX8E
HOPL paper: https://hopl4.sigplan.org/details/hopl-4-papers/10/JavaScrip...
* The other person with an office opening into Keith's work area at Memex was Ron Resch https://www.historyofcg.com/pages/university-of-utah/
Why didn't I step in and help poor Keith? Ever heard of Croquet's TeaTime?
https://dl.acm.org/doi/abs/10.1145/1094855.1094861
I was in a position to resurrect at least _that_ much of the original work I'd one at Viewtron Corp. of America based on David P. Reed's PhD thesis, and Reed was just down the street from us at Interval Research at that time, which rather tempted me away from helping Keith, even if I'd been authorized to do so, which I wasn't.