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I ended up going in a  completely different direction with this: I intend to test my OWN rationality, and I figure that if rationality is about WINNING, about being EFFECTIVE, then I ought to find direct measures of the things I want, and test myself in 6 months or so (timeframe dependent on the toughness/length of the task). This will, in other words, be a test of my ability to understand the territory insofar as that understanding makes me more effective at a given task.

The things in particular, a few subgoals of my personal life-optimization:

  • artistic endeavors and life enjoyment: engaging in things like art or gamedev or other mediums while aiming for MAXIMUM FUN.
  • being RESTED, having ENERGY to do things (I have a tendency to burn out due to overworking myself)
  • studying AI alignment (and the general objective of "actually have a positive effect on whether we're all going to die or not")

the tests in question:

  • for each artistic project (i.e. a drawing, a game, et cetera), I post it to a public forum and, with said post, I add a simple strawpoll asking "would you judge this work as 'complete'?" I would not be allowed to argue with the results, and I'd be judged by the number of projects I complete, with "complete" defined by the poll being greater than 80%. It's hard to directly measure fun, but "completing quality projects and showing them to others" seems like a good enough way to achieve it, for me in particular.
  • I've already got a method for measuring this: each day, if I notice that I'm tired during my free time, I force myself to rest until I stop being tired, and I record the time in a spreadsheet. Then, I sum up all the rest time accumulated over a period of a month. The lower it is, the better my sleep patterns hypothetically are. I predict that, if I had myself do this for as long as a month, I'd avoid pushing myself to my productive limit - that would induce burnout, which would eventually FORCE me to rest during free time, and a lot.
  • A good measure of "you are making quality posts" would be either something like summed upvotes, or maximum upvotes on a post in a given period, or maximum links from other posts made by other users. That last one seems difficult, but also points me in the right direction of "look into what posts got referenced the most, and try to make those kinds of insights."

I'm a little bit nervous about taking on the 1st or 3rd test - I'm not sure if I could pull them off - but I suppose that's the right feeling to have, if they're hard but accurately so

Ah, speaking at a convention or a similar environment seems like a good idea, I have opportunities like that I can immediately think of. 

Can you elaborate on the usefulness of public speaking, though? You mentioned gaining status, and I could see that as somewhat useful for making myself more well-known -> gaining connections -> being offered better opportunities, but there's probably uses for it or consequences of it that I haven't thought of.

oh - and regarding this:

I think the musical skills are probably not worth it, unless it is something you really want to do.

Upon reading this, I had an instinctive negative reaction to you saying that they weren't worth it. So I suspect it is something I really want to do, or at least that something involved in giving up on it goes against my internal values.

I think you're right about social skills like public speaking or communication generally being important, those sorts of things are definitely scary to me but they'd definitely make me more effective at whatever I end up pursuing. 

I'll probably be practicing those communication skills here, first - I hope to write a lot more posts in the future, since exploring my ideas in written form in various notebooks has already been a habit of mine for a while. "Learn how to network" is also on my todo list, and friendmaking as well. My whole social toolkit generally needs some work.

You recommend that I try to make more money - once again, this is one of those cases where I've got an instinct to avoid it, but in the abstract I understand its usefulness. My brain brings up points like "people with more money have more opportunities to do bad things, like buying drugs or bribing others," and "if you truly did get more money, people would judge you as a bad person for it." I hadn't questioned these internal points much before, but you're right that getting money is an instrumental goal for all kinds of things I might want to accomplish.

For now, I'm focusing on studying in the spare time I have available, while making decisions based on the goal of "actually solving alignment." I think I'll do some writing/thinking in the near future, about how to also use my personal resources to make some money, without sacrificing too much progress towards said goal.

I had a similar experience, for sure. See the post immediately above yours, when sorted by "newest." Do you want to share your story here?

This wasn't precisely the reason I got here, but I think the biggest reason that I was open to the idea of rationality when I finally stumbled upon LessWrong and the whole Effective Altruism idea was my experience of becoming gay, after diverging from my christian upbringing. 

During my time going to bible school (yes, I was in that deep), there was a lot of theology where I was confused and felt like I didn't understand why something was true, but just accepted that "I'm sure some high-level theologian out there has a reasonable answer for this, I just don't know it." However, once I began living on my own, naturally drifted away from the church, and then discovered that gay stuff wasn't as bad as I'd been told, I realized (this is how I think of it now) that there was a very large black mark on the source of knowledge internally labelled as "religious authority." That was the first frayed thread in that anachronistic tapestry I had properly seen unraveled for myself, and I suspect that there are many more of such threads that I overlooked previously.