What is your opinion on rationality-promoting articles by Gleb Tsipursky / Intentional Insights? Here is what I think:
Trying to teach someone to think rationally is a long process -- maybe even impossible for some people. It's about explaining many biases that people do naturally, demonstrating the futility of "mysterious answers" on gut level; while the student needs the desire to become stronger, the humility of admitting "I don't know" together with the courage to give a probabilistic answer anyway; resisting the temptation to use the new skills to cleverly shoot themselves in the foot, keeping the focus on the "nameless virtue" instead of signalling (even towards the fellow rationalists). It is a LW lesson that being a half-rationalist can hurt you, and being a 3/4-rationalist can fuck you up horribly. And the online clickbait articles seem like one of the worst choices for a medium to teach rationality. (The only worse choice that comes to my mind would be Twitter.)
On the other hand, imagine that you have a magical button, and if you press it, all not-sufficiently-correct-by-LW-standards mentions of rationality (or logic, or science) would disappear from the world. Not to be replaced by something more lesswrongish, but simply by anything else that usually appears in the given medium. Would pressing that button make the world a more sane place? What would have happened if someone had pressed that button hundred years ago? In other words, I'm trying to avoid the "nirvana fallacy" -- I am not asking whether those articles are the perfect vehicle for x-rationality, but rather, whether they are a net benefit or a net harm. Because if they are a net benefit, then it's better having them, isn't it?
Assuming that the articles are not merely ignored (where "ignoring" includes "thousands of people with microscopic attention spans read them and then forget them immediately), the obvious failure mode is people getting wrong ideas, or adopting "rationality" as an attire. Is it really that wrong? Aren't people already having absurdly wrong ideas about rationality? Remember all the "straw Vulcans" produced by the movie industry; Terminator, The Big Bang Theory... Rationality already is associated with being a sociopathic villain, or a pathetic nerd. This is where we are now; and the "rationality" clickbait, however sketchy, cannot make it worse. Actually, it can make a few people interested to learn more. At least, it can show people that there is more than one possible meaning of the word.
To me it seems that Gleb is picking the low-hanging fruit that most rationalists wouldn't even touch for... let's admit it... status reasons. He talks to the outgroup, using the language of the outgroup. But if we look at the larger picture, that specific outgroup (people who procrastinate by reading clickbaity self-improvement articles) actually aren't that different from us. They may actually be our nearest neighbors in the human intellectual space. So what some of us (including myself) feel here is the uncanny valley. Looking at someone so similar to ourselves, and yet so dramatically different in some small details which matter to us strongly, that it feels creepy.
Yes, this whole idea of marketing rationality feels wrong. Marketing is like almost the very opposite of epistemic rationality ("the bottom line" et cetera). On the other hand, any attempt to bring rationality to the masses will inevitably bring some distortion; which hopefully can be fixed later when we already have their attention. So why not accept the imperfection of the world, and just do what we can.
As a sidenote, I don't believe we are at risk of having an "Eternal September" on LessWrong (more than we already have). More people interested in rationality (or "rationality") will also mean more places to debate it; not everyone will come here. People have their own blogs, social network accounts, et cetera. If rationality becomes the cool thing, they will prefer to debate it with their friends.
EDIT: See this comment for Gleb's description of his goals.
Not sure if it makes any difference, but instead of "stupid people" I think about people reading articles about 'life hacking' as "people who will probably have little benefit from the advice, because they will most likely immediately read hundred more articles and never apply the advice"; and also that the format of the advice completely ignores the inferential distances, so pretty much the only useful thing such article could give you is a link to a place that provides the real value. And if you are really really lucky, you will notice the link, follow the link, stay there, and get some of the value.
If I'd believe the readers were literally stupid, then of course I wouldn't see much value in advertising LW to them. LW is not useful for stupid people, but can be useful to people... uhm... like I used to be before I found LW.
Which means, I used to spend a lot of time browsing random internet pages, a few times I found a link to some LW article that I read and moved on, and only after some time I realized: "Oh, I have already found a few interesting articles on the same website. Maybe instead of randomly browsing the web, reading this one website systematically could be better!" And that was my introduction to the rationalist community; these days I regularly attend LW meetups.
Could Gleb's articles provide the same gateway for someone else (albeit only for a tiny fraction of the readership)? I don't see a reason why not.
Yes, the clickbait site will make money. Okay. If instead someone would make paper flyers for LW, then the printing company would make money.
Indeed, the people who read one of our articles, for example the Lifehack article, are not inherently stupid. They have that urge for self-improvement that all of us here on Less Wrong have. They just way less education and access to information, and also of course different tastes, preferences, and skills. Moreover, the inferential gap is huge, as you correctly note.
The question is what will people do: will they actually follow the links to get more deep engagement? Let's take the Lifehack article as an example to describe our broader model, which assumes that once people check out our content on other websites and venues, some will then visit the Intentional Insights website to engage with its content. So after the Lifehack article on 6 Science-Based Hacks for Growing Mentally Stronger appeared, it was shared over 2K times on social media, so it probably had views in the tens of thousands if not hundreds.
Then, over 1K people visited the Intentional Insights website directly from the Lifehack website. In other words, they were interested enough to not only skim the article, but also follow the links to Intentional Insights, which was listed in my bio and elsewhere. Of those, some will want to engage with our content further. As an example, we had a large wave of new people follow us on Facebook and other social media and subscribe to our newsletter in the week after the article came out. I can't say how many did so as a result of seeing the article or other factors, but there was a large bump. So there is evidence of people wanting to get more thoroughly engaged.
The articles are meant to provide a gateway, in other words. And there is evidence of people following the breadcrumbs. Eventually, after they receive enough education, we would introduce them to ClearerThinking, CFAR, and LW. We are careful to avoid Endless September scenarios by not explicitly promoting Less Wrong heavily. For more on our strategy, see my comment below.