Antisuji comments on Epistle to the New York Less Wrongians - Less Wrong
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It also has a more subtle and counterintuitive failure mode. People can derive status and get much satisfaction by handing out perfectly honest and well-intentioned advice, if this advice is taken seriously and followed. The trouble is, their advice, however honest, can be a product of pure bias, even if it's about something where they have an impressive track record of success.
Moreover, really good and useful advice about important issues often has to be based on a no-nonsense cynical analysis that sounds absolutely awful when spelled out explicitly. Thus, even the most well-intentioned people will usually be happier to concoct nice-sounding rationalizations and hand out advice based on them, thus boosting their status not just as esteemed advice-givers, but also as expounders of respectable opinion. At the end, you may well be better off with a rash "who is he to tell me what to do" attitude than with a seemingly rational, but in fact dangerously naive reasoning that you should listen to people when they are clearly knowledgeable and well-intentioned. (And yes, I did learn this the hard way.)
Things are of course different if you're lucky to know people who have the relevant knowledge and care about you so much that they'll really discard all the pious rationalizations and make a true no-nonsense assessment of what's best for you. You can expect this from your parents and perhaps other close relatives, but otherwise, you're lucky if you have such good and savvy friends.
The problem of getting good data on how other people see you is a topic I've been thinking about a lot lately. I'd love to see a top-level post on this, because I think it's pretty essential for many areas of self-improvement, and I'd write it myself but I don't think I have a clear enough idea of the problems involved. I didn't think about this particular failure mode, for example.
Alternatively, are there any other resources that can help me get this information?
On the off chance this will be spotted in the sidebar: I'm a couple years late responding, but has anyone written anything useful on this subject? Is anyone in a position to do so?
Getting a correct model of others' models of oneself, and knowing it's correct, seems ridiculously difficult to me.
I agree that this is a difficult problem. It seems to be that way because the incentive structure is misaligned for truth. The costs of giving someone unbiased feedback are mostly paid by the giver of the feedback, but the benefits are mostly received by the receiver of the feedback. Thus, this is very difficult to get from people who are not close friends and allies- but those people are probably ones who have an above-average view of you.
Thus, one of the low-hanging fruit here is rewarding negative feedback, which is in many ways more useful than positive feedback (and yet most people don't reward it).
It may be useful to ask people you trust questions like "How do you think other people view me?" The deflection to other people makes it easier to voice their personal concerns under plausible deniability, as well at getting at the question of "how do I present myself to others?" and "what features of my personality and behavior are most salient?"