I really liked the level of subtextual snark (e.g. almost every use of the word 'rational'). This level of skepticism and mockery is, frankly, about what should be applied, and was fun to read.
I was surprised at the density of weirdness, not because it makes bad journalism, but because it's difficult for the audience to understand (e.g. /r/hpmor is just dropped in there and the reader is expected to deal). I like Sarunas' explanation for this. Fairness-wise, this was better than I expected, though with occasional surrenders to temptation (The glaring one for me was Will and Divia Eden).
Michael Vassar as our face was inevitable if disappointing. The writing about him was great. I feel like the descriptions of his clothing are the author making him a little funnier - nobody else gets clothing description.
The author's initial inability to read lesswrong makes me think we may need a big button at the top that says "First time? Click here!" and just dumps you into a beginner version of the Sequences page.
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I recently watched this Coursera course on learning how to learn and your post uses different words for some of the same things.
The course described what you call "shower-thoughts" as "diffuse mode" thinking, with an opposite called "focused mode" thinking and the brain only able to do one at a time. Focused mode uses ideas that are already clustered together to solve familiar problems while diffuse mode attempts to find useful connections between unclustered ideas to solve new problems in new ways. Not sure if these are the formal/correct terms from the literature that was behind the class, but if so it might be worth using them instead of making up our own jargon.
As for the class it definitely had some stuff that I still try to keep in mind, but it also had some things that I haven't quite figured out how to incorporate (chunking) or didn't find useful (some of the interviews). There is some overlap with what CFAR seems to be trying to teach. Overall I'd recommend taking a look if you have an hour or so per week over a month for it.