How can I get help becoming a better rationalist?

Well, if you want the complicated answer: four or five years ago, about when I started lurking here, I came with a good mindset, and intent on learning skills rather than rules, for precisely the reason you mention. That was right before I entered university, and I think I screwed up that bit. Got depressed, and have remained too out of it to actually use rationality to improve my life much since then. But that’s changing, and the first step is to pick up my rationality practice where I left it four years ago, when I started focusing only on reading blog posts to forget them soon afterward. 
 

In other words: yeah, I know that ‘valley of bad rationality’ thing. Just digging myself out of one as we speak, actually. 
 

And, apart from that, thanks for the great advice. Will heed it :-)

I think this is incorrect. From Levels of Action [LW · GW]:

One of the most useful concepts I have learned recently is the distinction between actions which directly improve the world, and actions which indirectly improve the world.

Suppose that you go onto Mechanical Turk, open an account, and spend a hundred hours transcribing audio. At current market rates, you'd get paid around $100 for your labor. By taking this action, you have made yourself $100 wealthier. This is an example of what I'd call a Level 1 or object-level action: something that directly moves the world from a less desirable state into a more desirable state.

On the other hand, suppose you take a typing class, which teaches you to type twice as fast. On the object level, this doesn't move the world into a better state- nothing about the world has changed, other than you. However, the typing class can still be very useful, because every Level 1 project you tackle later which involves typing will go better- you'll be able to do it more efficiently, and you'll get a higher return on your time. This is what I'd call a Level 2 or meta-level action, because it doesn't make the world better directly - it makes the world better indirectly, by improving the effectiveness of Level 1 actions. There are also Level 3 (meta-meta-level) actions, Level 4 (meta-meta-meta-level actions), and so on.

 

The most important difference between Level 1 and Level 2 actions is that Level 1 actions tend to be additive, while Level 2 actions tend to be multiplicative. If you do ten hours of work at McDonald's, you'll get paid ten times as much as if you did one hour; the benefits of the hours add together. However, if you take ten typing classes, each one of which improves your ability by 20%, you'll be 1.2^10 = 6.2 times better at the end than at the beginning: the benefits of the classes multiply (assuming independence).

I too like the idea of rationality being about winning (although you can also argue that it is about epistemics independent of how epistemics relate to winning). But I think that rationality usually helps with winning via high level actions. For example, learning about biases is a high level action that helps in a whole bunch of different scenarios.

That said, I also agree with the author of Levels of Action's warning about focusing too much on high levels of action.

It is also possible to have the opposite problem, of under-valuing Level 1, and I suspect that quite a few people in the nerdier communities do. People sometimes fall into the trap of noticing that the higher levels are (when applied properly) far more useful on the margin than Level 1, and then reacting by giving blind praise [? · GW] to the meta level at the expense of the object level. One cultural example is the ancient Greeks- who, though they were good thinkers for their day, didn't invent science. Science involved actually going out and looking at the world [? · GW], and that was manual labor and manual labor was for slaves. The ultimate extreme of this is Aristotle, who got philosophy off to an unfortunate beginning by starting his Metaphysics with the assumption that the most noble knowledge would be the most useless.

The problem there is that, because Level 2 actions are multiplicative and not additive, you still need at least some Level 1 actions to multiply by. It doesn't matter how high the value of one's labor is, if one never actually goes out and does labor. A very large number, multiplied by zero, is still zero. If one just does Level 2 actions, without any Level 1 actions, it is a failure to do something instead of nothing. Taking only meta-level actions accomplishes less, in the end, than the ten-year-old who just mowed the neighbor's lawn for a dollar.

How did I not notice ‘systematized winning’ meant that? I think I actually had no clue what it meant :/ Still, sounds great! And it’s actually a big part of what I’m trying to do, but I’ve been depressed for a long while and it’s only getting better now, so I’m a bit late at that game :-)

So, I’ll have to find a goal. Even then, that sounds way easier to do in the Bay, where one supposedly has other LWers around to talk to, but that shouldn’t be too much of a problem

What good things have you heard, could you be more specific?

Seems really interesting! Like, really interesting! Thanks

Will do this evening, thanks for the advice!

Interesting comment. You know, the weird thing is that I knew all of that long before I started implementing it (that is, quite recently). And it’s not even surprising that for the longest time I knew that avoiding bad situations, making logs, making a deliberate effort to stay healthy, and avoiding self-punishment were important, but that I hardly ever did any of it. I don’t think I quite grok fully why our brains work like that.
 

And now, I’m actually a little concerned that I may have taken up negative reinforcement and other such bad habits in a way where it’ll be hard to uproot them. I guess if there is good advice on that, I could probably use it.