Why might people give up on learning philosophy or learning to be a great (critical) thinker?
I think maybe no one has ever quit my community while making rapid progress.
Maybe people only quit when they get fully stuck or progress gets too slow.
How/why do they get stuck?
People are very resistant to doing easy/childish/basic stuff. They want to do complex stuff which they think is more interesting, less boring, more impressive, more important, etc. When they do harder and more complicated stuff, I regard it as skipping steps/prerequisites which leads directly to an overwhelmingly high error rate. They may experience their high error rate as e.g. me having 10 criticisms for each of their posts, which they can't deal with so they might blame the messenger, me. They may be blind to their high error rate because they don't understand what they're doing enough to spot or understand the errors (due to the missing prerequisites, skipped steps) or because they have low standards (they're used to being partially confused and calling that success and moving on – that's how they have dealt with everything complicated since age 5).
People may be disorganized. If you successfully do many tiny projects which don't skip steps, that will only translate into substantive progress if you are following some plan/path towards more advanced stuff and/or you integrate multiple smaller things into more complex stuff.
People may have some hangup/bias and be unwilling to question/reconsider some particular idea.
People are often very hostile to meta discussion. This prevents a lot of problem solving, like doing workarounds. Like if they are biased about X, you could have a meta discussion about how to make progress in a way that avoids dealing with X. It’s completely reasonable to claim “You may be biased about X. I think you are. If you are and we ignore it and assume you aren’t, that could make you stuck. So let’s come up with a plan that works if you are biased about X and also works if you aren’t biased about X.” In other words, we disagree about something (whether you’re biased or wrong about X) and can’t easily agree, so we can come up with a plan that works regardless of who is right about the disagreement. People have trouble treating some of their knowledge as unreliable when it feels reliable to them. Their subconscious intuitions treat it as reliable, and they are bad at temporarily turning those off (in a selective way for just X) or relying on conscious thought processes for dealing with this specific thing. They’re also bad at quickly (and potentially temporarily) retraining their subconscious intuitions.
More broadly if there is any impasse in a discussion, you could meta-discuss a way to proceed productively that avoids assuming a conclusion about the impasse, but people tend to be unwilling to engage in that sort of (meta) problem solving. You can keep going productively in discussions, despite disagreements, if you are willing to come up with neutral plans for continuing that can get a good result regardless of who was right about the disagreement. But people usually won’t do that kind of meta planning and seem unwilling to take seriously that they might be wrong unless you actually convince them that they are wrong. They just want to debate the issue directly, and if that gets stuck, then there’s no way to make progress because they won’t do the meta technique. Or if they will do a meta level, they probably won’t do 5 meta levels to get past 5 disagreements (even with no nesting – just 5 separate, independent disagreements, which is easier than nested disagreements), so you’ll get stuck later.
The two big themes here are people get stuck because they try to build advanced knowledge on an inadequate foundation and they don’t want to work on the foundation. And they have issues with problem solving and get stuck on problems and won’t meta discuss the problems (talking about the problem itself, rather than continuing the original discussion).
Lots of this stuff happens alone. Like biased people might get stuck because they’re biased. And even if they realize they might be wrong or biased about a specific thing, they can still get stuck similar to if I pointed out a potential error or bias.
One pattern I’ve seen is people make progress at first, and then the first time they run into a problem that they get stuck on for a week, they never solve it. That can lead to quitting pretty quickly or sometimes many months later if they keep trying other stuff. When trying other stuff, they will occasionally run into another problem they don’t solve, so the list of unsolved problems grows. They made initial progress by solving problems they found easy (ones their intuitions were good at or whatever), but unless they can solve problems they find hard, they are screwed in the long run.
Regarding going back to less complex stuff to improve knowledge quality, sometimes people try that but run into a few problems. One, they go back to a lot more basic than they’re used to and still make tons of errors and they don’t want to go back way further. Two, they do some basic stuff but are not able to connect it to the more advanced stuff and use it – they aren’t organized enough, don’t integrate enough, do conscious review but don’t change their subconscious, or don’t understand the chain of connections from the basic stuff to the advanced stuff well enough.