"I suppose that you are less happier (though probably not in any way perceivable from a first person perspective) but way more relaxed, prone to be guided by your desires and wishes, and willing to actually go there and do that thing you feel like doing....."

What makes you think that the person you are responding to is more relaxed? You'd think that constantly pursuing wants would make them less relaxed since it takes a lot of energy to pursue worldly things.

And, what you think that you aren't relaxed?

Would you consider a topic related to the "herding cats" category?

Mentoring, that is.

Lack of engagement with the established members is definitely a big barrier encountered by newcomers. You wouldn't expect to gain converts as a missionary just by uploading the Holy Bible to the internet page by page and giving each page a comments section, or by posting your personal insights about your religion onto this site. And yet, this is essentially what newcomers experience on LW.

I like your idea to get veterans of this community to have a conversation with newcomers, but I don't think just one conversation is enough. If this was taken one step further, then we could have a system similar to the university research system. One "professor" takes on a group of "undergrads" and guides them on their way to overcoming their biases. Another benefit would be that each student now has an immediate group of people at about the same rationality level with whom they can discuss what they are currently learning, and the leader can recognize if the group is covering new ground or if they are beginning to miss the point.

This is essentially how the Bayesian Conspiracy system works in the beisutsukai series, anyway. It would be incredibly cool, especially to "students" like me, if you "sensei"s actually went ahead and implemented this system.

Edit: the actual implementation depends on the geographic distribution of people willing to become teachers. If most of the teachers are just concentrated in the Silicon Valley area, then maybe an online system could work, where each "group" of learners communicates with each other through a mailing list. When the community gets big enough, some of the regional meet-ups could turn into sessions for the Bayesian Conspiracy.