Eliezer Yudkowsky's speaks in "What Do We Mean By "Rationality"? about two ways to understand rationality:
You could say that focusing on 1. automatically improves 2. That might be so because by making your maps more accurate by means of closing the gap of your models to reality you increase the change for succeeding in 2. Or said differently, its harder to arrive where you want if your map is wrong.
On the otherhand it might be better to be interesting and wrong than boring and right.
This is another observer tribe, and possibly the most interesting one. If the rationalist motto is “the map is not the territory, but it is important to create the most accurate map possible,” then the post-rationalist motto is “the canvas is not the territory, but it is important to create the most interesting canvas possible.” This observer tribe has the potential to generate innovative solutions to the seemingly intractable problem of the differend.
What i think he is pointing to is that the term post-rationalist (in his view) points to the possibility to derive insights more from a state of flow than a state of hard thinking. This might come clearer by revieling a seeming nuance/distiction to the post-rationalist approach.
The skill-set of insight generation for its own sake is good practice, but I think it has to grow out of the realm of masturbation and into the realm of lovemaking.
What i think what he is refering to is similar to what Bill Hicks concludes in "It's Just A Ride" about the choice between fear and love.
post-rationality
para-rationality
meta-rationality
communites/plattforms
There seems to be a fundamental need to distinguish reasonableness, rationality, and meta-rationality to capture the understanding.
But by distinguishing meta-rationality from rationality and reasonableness, we can talk about getting better at all three without saying that all three must better approximate the One True Way.
The Twelfth Virtue, the "nameless" one points to the moon that the three "schools" seem to be about. It seams meta-rationality helps in comprehending the "nameless" in a better way than rationality.
There is also the term "rationalist eternalism" that Chapman uses to point to the week link in rationality. It is about the trap to think that there is the One True Way to understand things and is specially characterized by ingnore context. There is the phrase to say "the map is not the territory". To understand meta-rationality is about also understanding that "there is no map that can perfectly match the territory" and "determining what the territory is (ontology) depends on context-sensitive judgments of relevance."
Is/Ought distiction is about a question of how can science answer best what Is and what Ought to be. It comes down to how to choose values. Ethics?
Rationality seems to be detached from purpose and values. Thats also the main critic to the scientific approach. But the rational frameworks seems to be aware of this and speak about the need of having something they value more than "rationality"
It seems to come down to how we can best capture the combinatory explosive nature of reality without loosing ourself too much in dead-ends (outside-the-box).