Thanks for spotting.This is rich:

As are some of the comments, especially this

What is Fae counting as a 'classic' problematic organization here? At least I think I understand that puzzling word 'outreach'. It means going to people and organisations and institutions that exist in the wide world outside Wikipedia, and telling them how good Wikipedia is. I wonder now they have all that money, whether they could employ a PR firm to do this?

Oh and I just saw this

Professionally, the biggest lesson I learned was, except in the rarest of circumstances, that it was never appropriate to apportion blame if you want to have constructive relationships. In fact, I usually went overboard to ensure that the other side felt that they had solved problems themselves. Not only do people work better, it also doesn't blow back on you when you discover you'd been an idiot yourself (Jimbo take note!). The only time I would ever say "you screwed up there" would be with a big grin when the poor soul who had just done the recursive delete all on the root directory of the live production machine, when he and everyone else knew it to be true and they also knew that we were all going to work together to sort it out.

As far as Wikipedia is concerned, the lesson that they have totally failed to learn is that they should always assume that it is Wikipedia's own fault that outsiders do not understand how it works. For example, for all the money the WMF has gathered, where is the "Manual for Business Use" or "How to use Wikipedia successfully" book.

This is a double failure because the initial exhortation is "Just get stuck in". Jimbo is charging around essentially calling intelligent people idiots because they are bemused by the bizarre and illogical way Wikipedia is claimed to work (especially when it clearly does not work the way Jimbo thinks it might do).

It is classic programmer attitude: user error. Computers are hard work and I basically left the computer industry because I was fed up of how it has let people down in many ways. Wikipedia is a classic case of a poor computer system where the programmers blame the users for not being able to use the system.

If Wikipedians for one minute assumed that they had the problem, not the whole rest of the world, then they might then start thinking clearly about how to operate. For example, in these GLAM projects, they might discover that there is a better way of working. Instead, we can guarantee that they will drive people off casually or deliberately without it ever occurring to them that they had lost something to the project, and they will pat each other on the back for driving out the misfits. "Why didn't Joe90 turn up last week to the Monmouthshire meeting? I really needed to sort him out for all the fuck ups I told him about. Had to block the idiot - he seemed to think that being a professor of history counted for something in a history project - what a dork!"

That would be a waste of the money that should be going to genuinely useful charity activities. Like, hiring people to raise more money.

What, show these paid editors how to game the system properly?

There is no need to worry. Despite Jimbo's "outreach" to the horrid infidels, this won't get past The Wiki Holy Office. Heretics and apostates are for burning; the fires have never gone out.

Sometimes I envy the people that live in mom's basement. Life can only get better, right?

My parents' basement is distinctly damp. I'd call it unfit for human habitation, though arguably not unfit for WP editors.

Fortunately, when we stay with them we can use an upstairs bedroom.