I've noticed a serious problem in which aspiring rationalists vastly overestimate their ability to optimize other people's lives. And I think I have some idea of how the problem arises.
You read nineteen different webpages advising you about personal improvement—productivity, dieting, saving money. And the writers all sound bright and enthusiastic about Their Method, they tell tales of how it worked for them and promise amazing results...
But most of the advice rings so false as to not even seem worth considering. So you sigh, mournfully pondering the wild, childish enthusiasm that people can seem to work up for just about anything, no matter how silly. Pieces of advice #4 and #15 sound interesting, and you try them, but... they don't... quite... well, it fails miserably. The advice was wrong, or you couldn't do it, and either way you're not any better off.
And then you read the twentieth piece of advice—or even more, you discover a twentieth method that wasn't in any of the pages—and STARS ABOVE IT ACTUALLY WORKS THIS TIME.
At long, long last you have discovered the real way, the right way, the way that actually works. And when someone else gets into the sort of trouble you used to have—well, this time you know how to help them. You can save them all the trouble of reading through nineteen useless pieces of advice and skip directly to the correct answer. As an aspiring rationalist you've already learned that most people don't listen, and you usually don't bother—but this person is a friend, someone you know, someone you trust and respect to listen.
And so you put a comradely hand on their shoulder, look them straight in the eyes, and tell them how to do it.
I, personally, get quite a lot of this. Because you see... when you've discovered the way that really works... well, you know better by now than to run out and tell your friends and family. But you've got to try telling Eliezer Yudkowsky. He needs it, and there's a pretty good chance that he'll understand.
It actually did take me a while to understand. One of the critical events was when someone on the Board of the Institute Which May Not Be Named, told me that I didn't need a salary increase to keep up with inflation—because I could be spending substantially less money on food if I used an online coupon service. And I believed this, because it was a friend I trusted, and it was delivered in a tone of such confidence. So my girlfriend started trying to use the service, and a couple of weeks later she gave up.
Now here's the the thing: if I'd run across exactly the same advice about using coupons on some blog somewhere, I probably wouldn't even have paid much attention, just read it and moved on. Even if it were written by Scott Aaronson or some similar person known to be intelligent, I still would have read it and moved on. But because it was delivered to me personally, by a friend who I knew, my brain processed it differently—as though I were being told the secret; and that indeed is the tone in which it was told to me. And it was something of a delayed reaction to realize that I'd simply been told, as personal advice, what otherwise would have been just a blog post somewhere; no more and no less likely to work for me, than a productivity blog post written by any other intelligent person.
And because I have encountered a great many people trying to optimize me, I can attest that the advice I get is as wide-ranging as the productivity blogosphere. But others don't see this plethora of productivity advice as indicating that people are diverse in which advice works for them. Instead they see a lot of obviously wrong poor advice. And then they finally discover the right way—the way that works, unlike all those other blog posts that don't work—and then, quite often, they decide to use it to optimize Eliezer Yudkowsky.
Don't get me wrong. Sometimes the advice is helpful. Sometimes it works. "Stuck In The Middle With Bruce"—that resonated, for me. It may prove to be the most helpful thing I've read on the new Less Wrong so far, though that has yet to be determined.
It's just that your earnest personal advice, that amazing thing you've found to actually work by golly, is no more and no less likely to work for me than a random personal improvement blog post written by an intelligent author is likely to work for you.
"Different things work for different people." That sentence may give you a squicky feeling; I know it gives me one. Because this sentence is a tool wielded by Dark Side Epistemology to shield from criticism, used in a way closely akin to "Different things are true for different people" (which is simply false).
But until you grasp the laws that are near-universal generalizations, sometimes you end up messing around with surface tricks that work for one person and not another, without your understanding why, because you don't know the general laws that would dictate what works for who. And the best you can do is remember that, and be willing to take "No" for an answer.
You especially had better be willing to take "No" for an answer, if you have power over the Other. Power is, in general, a very dangerous thing, which is tremendously easy to abuse, without your being aware that you're abusing it. There are things you can do to prevent yourself from abusing power, but you have to actually do them or they don't work. There was a post on OB on how being in a position of power has been shown to decrease our ability to empathize with and understand the other, though I can't seem to locate it now. I have seen a rationalist who did not think he had power, and so did not think he needed to be cautious, who was amazed to learn that he might be feared...
It's even worse when their discovery that works for them, requires a little willpower. Then if you say it doesn't work for you, the answer is clear and obvious: you're just being lazy, and they need to exert some pressure on you to get you to do the correct thing, the advice they've found that actually works.
Sometimes—I suppose—people are being lazy. But be very, very, very careful before you assume that's the case and wield power over others to "get them moving". Bosses who can tell when something actually is in your capacity if you're a little more motivated, without it burning you out or making your life incredibly painful—these are the bosses who are a pleasure to work under. That ability is extremely rare, and the bosses who have it are worth their weight in silver. It's a high-level interpersonal technique that most people do not have. I surely don't have it. Do not assume you have it, because your intentions are good. Do not assume you have it, because you'd never do anything to others that you didn't want done to yourself. Do not assume you have it, because no one has ever complained to you. Maybe they're just scared. That rationalist of whom I spoke—who did not think he held power and threat, though it was certainly obvious enough to me—he did not realize that anyone could be scared of him.
Be careful even when you hold leverage, when you hold an important decision in your hand, or a threat, or something that the other person needs, and all of a sudden the temptation to optimize them seems overwhelming.
Consider, if you would, that Ayn Rand's whole reign of terror over Objectivists can be seen in just this light—that she found herself with power and leverage, and could not resist the temptation to optimize.
We underestimate the distance between ourselves and others. Not just inferential distance, but distances of temperament and ability, distances of situation and resource, distances of unspoken knowledge and unnoticed skills and luck, distances of interior landscape.
Even I am often surprised to find that X, which worked so well for me, doesn't work for someone else. But with so many others having tried to optimize me, I can at least recognize distance when I'm hit over the head with it.
Maybe being pushed on does work... for you. Maybe you don't get sick to the stomach when someone with power over you starts helpfully trying to reorganize your life the correct way. I don't know what makes you tick. In the realm of willpower and akrasia and productivity, as in other realms, I don't know the generalizations deep enough to hold almost always. I don't possess the deep keys that would tell me when and why and for who a technique works or doesn't work. All I can do is be willing to accept it, when someone tells me it doesn't work... and go on looking for the deeper generalizations that will hold everywhere, the deeper laws governing both the rule and the exception, waiting to be found, someday.
If you have already decided to spend many tens of hours reading, then perhaps doing the sequences in order would best achieve that. However, if you have already so decided, you probably need to read this first and take it heart.
If you have decided to spend a few tens of hours, there are 62 posts on commonsenseatheism.com in an ongoing series called "reading Yudkowsky" that outlines chunks of posts, also in order.
This article is a good one to start with, and you can see how the wiki here summarizes concepts from such articles.
Asking questions is always perfectly fine.
A web search for videos and podcasts by Yudkowsky are potentially very useful for certain types of learners, as they contain visuals and the cues of communication that are lost in the text format.
I recommend thinking about some things you are looking for from a post in terms of style and what you want out of it, asking many people what they think would be best to start with based on that, seeing which responses were common, and working to understand those, if it takes effort. Then, I would describe briefly in a discussion section post which of the commonly recommended posts you liked and why, as well as which of them you disliked and why, and ask for further recommendations based on that.
I think this is a good approach to the material because one asks for optimal posts based on one's own criteria. There are advantages to the sequential way, as the posts were written to be read that way.
Here is one person's top fifteen list, of which (now these have been recommended by two people) I recommend this this and this.
It may be that other writers happen write more in consonance with how you think, in which case you might want to look at Yvain's posts, of which this, this and this are some of my favorites.
It may be best to start by reading the material easiest to digest, which may be in story format - similarly, dialogues are often relatively very accessible.
You've given me some information, so my advice for which particular ones to read wouldn't strictly be my favorite posts. I think the first two I linked to from lukeprog's favorites help show that some ideas that are deeply theoretical are also totally natural.
Here are some links to some posts I think would make a good introduction.
If there is only one piece of advice that is more important than any other, it is the following: DON'T PANIC.