I don't think that's right—

My life experiences during the (now bygone) Shirky era and the loose school associated with it really inculcated (in me, at least) the value of small, cumulative improvements contributed by folks on a wide scale. See something wrong? Fix it. Can't fix it (like, say, because you don't have the appropriate authorization)? File a bug so the people who can fix it know that it should be fixed. This matches exactly the description of seeing the "little flaws in everything you see in the world, and focus[ing] on those".

Looking at those flaws and thinking "this thing isn't as good as it could be" is a necessary first step for optimism. That belief and the belief in the possibility of getting it fixed is the optimist approach.

When I think of miserable people (and the ones who make me miserable), it's the ones who take the attitude of resignation that everything is shit and you shouldn't bother trying to change it because of how futile it is.

I think the default assumption that this is what's going on is a huge part of the problem. I see a similar thing happen on GitHub constantly, where project maintainers try to "upperhand" contributors, because they see the contribution as something deliberately undertaken to benefit the person who is e.g. submitting a bug report. This is a massive shift away from the spirit of the mid-to-late 2000–2010 era characterized by initiatives like Wikipedia (and wikis generally) and essays by Shirky on the adhocracy around the new digital commons.

In his response, Shirky responds that he was unable to keep up with overhead of running a WordPress blog, so it fell into disrepair and eventually disappeared.

Is this proof, from one of the biggest social critics on the topic of crowdsourcing (known for taking a favorable stance on it), that it doesn't work? Separately, is the promise of the Web itself a false one?

I'm not going to say "yes", but I will say—and have said before—that the "New Social" era of the 2010s saw a change of environment from when Here Comes Everybody was written. I think it highlights a weakness of counter-institutional organization—by definition the results aren't "sticky"—that's the purview of institutions. What's more, even institutions aren't purely cumulative.

This comment in 2010 highlights a difference between the world at large at that time (what I've called "the Shirky era") versus the behavior of users today

I've mentioned before that the era we're currently living in is incredibly different from the era of just 10–15 years ago. I've called the era of yesterdecade (where the author of this piece appeared on Colbert a ~week or so after Firefox 3 was released and implored the audience to go download it and start using it) the "Shirky era", since Shirky's Here Comes Everybody really captures the spirit of the times.

The current era of Twitter-and-GitHub has a distinct feel. At least, I can certainly feel it, as someone who's opted to remain an outsider to the T and G spheres. There's some evidence that those who haven't aren't really able to see the distinction, being too close to the problem. Young people, of course, who don't really have any memories of the era to draw upon, probably aren't able to perceive the distinction as a rule.

I've also been listening to a lot of "old" podcasts—those of the Shirky era. If ever there were a question of whether the perceived distinction is real or imagined these podcasts—particularly shows Jon Udell was involved with, which I have been enjoying immensely—eliminate any doubts about its existence. There's an identifiable feel when I go back and listen to these shows or watch technical talks from the same time period. We're definitely experiencing a lowpoint in technical visions. As I alluded to earlier, I think this has to do with a technofetishistic focus on certain development practices and software stacks that are popular right now—"the way" that you do things. Wikis have largely fallen by the wayside, bugtrackers are disused, and people are pursuing busywork on GitHub and self-promoting on social media to the detriment of the things envisioned in the Shirky era.