Introduction

Less Wrong is explicitly intended is to help people become more rational.  Eliezer has posted that rationality means epistemic rationality (having & updating a correct model of the world), and instrumental rationality (the art of achieving your goals effectively).  Both are fundamentally tied to the real world and our performance in it - they are about ability in practice, not theoretical knowledge (except inasmuch as that knowledge helps ability in practice).  Unfortunately, I think Less Wrong is a failure at instilling abilities-in-practice, and designed in a way that detracts from people's real-world performance.

It will take some time, and it may be unpleasant to hear, but I'm going to try to explain what LW is, why that's bad, and sketch what a tool to actually help people become more rational would look like.

(This post was motivated by Anna Salomon's Humans are not automatically strategic and the response, more detailed background in footnote [1].)

Update / Clarification in response to some comments: This post is based on the assumption that a) the creators of Less Wrong wish Less Wrong to result in people becoming better at achieving their goals (instrumental rationality, aka "efficient productivity"), and b) Some (perhaps many) readers read it towards that goal.  It is this I think is self-deception.  I do not dispute that LW can be used in a positive way (read during fun time instead of the NYT or funny pictures on Digg), or that it has positive effects (exposing people to important ideas they might not see elsewhere).  I merely dispute that reading fun things on the internet can help people become more instrumentally rational.  Additionally, I think instrumental rationality is really important and could be a huge benefit to people's lives (in fact, is by definition!), and so a community value that "deliberate practice towards self-improvement" is more valuable and more important than "reading entertaining ideas on the internet" would be of immense value to LW as a community - while greatly decreasing the importance of LW as a website.

Why Less Wrong is not an effective route to increasing rationality.

Definition:

Work: time spent acting in an instrumentally rational manner, ie forcing your attention towards the tasks you have consciously determined will be the most effective at achieving your consciously chosen goals, rather than allowing your mind to drift to what is shiny and fun.

By definition, Work is what (instrumental) rationalists wish to do more of.  A corollary is that Work is also what is required in order to increase one's capacity to Work.  This must be true by the definition of instrumental rationality - if it's the most efficient way to achieve one's goals, and if one's goal is to increase one's instrumental rationality, doing so is most efficiently done by being instrumentally rational about it. [2]

That was almost circular, so to add meat, you'll notice in the definition an embedded assumption that the "hard" part of Work is directing attention - forcing yourself to do what you know you ought to instead of what is fun & easy.  (And to a lesser degree, determining your goals and the most effective tasks to achieve them).  This assumption may not hold true for everyone, but with the amount of discussion of "Akrasia" on LW, the general drift of writing by smart people about productivity (Paul Graham: Addiction, Distraction, Merlin Mann: Time & Attention), and the common themes in the numerous productivity/self-help books I've read, I think it's fair to say that identifying the goals and tasks that matter and getting yourself to do them is what most humans fundamentally struggle with when it comes to instrumental rationality.

Figuring out goals is fairly personal, often subjective, and can be difficult.  I definitely think the deep philosophical elements of Less Wrong and it's contributions to epistemic rationality [3] are useful to this, but (like psychedelics) the benefit comes from small occasional doses of the good stuff.  Goals should be re-examined regularly, but occasionally (roughly yearly, and at major life forks).  An annual retreat with a mix of close friends and distant-but-respected acquaintances (Burning Man, perhaps) will do the trick - reading a regularly updated blog is way overkill.

And figuring out tasks, once you turn your attention to it, is pretty easy.  Once you have explicit goals, just consciously and continuously examining whether your actions have been effective at achieving those goals will get you way above the average smart human at correctly choosing the most effective tasks.  The big deal here for many (most?) of us, is the conscious direction of our attention.

What is the enemy of consciously directed attention?  It is shiny distraction.  And what is Less Wrong?  It is a blog, a succession of short fun posts with comments, most likely read when people wish to distract or entertain themselves, and tuned for producing shiny ideas which successfully distract and entertain people.  As Merlin Mann says: "Joining a Facebook group about creative productivity is like buying a chair about jogging".  Well, reading a blog to overcome akrasia IS joining a Facebook group about creative productivity.  It's the opposite of this classic piece of advice.