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For example, if a student tells me that I'm the worst teacher he or she has ever had, it makes me feel bad because I feel like I'm not contributing value, but I'm not at all upset with the student: my attitude is that the student is conveying valuable information to me, and that I should be appreciative.
I'm tempted to take that as a Crocker's rule invocation. But I have realized that you wrote this for people-like-you, that is, after all, pretty much its explicit purpose. As such, I'm not sure I have an criticism that I can't definitively think is helpful.
Nonetheless, I want to point out two general things about this will make this hard post to read for most people. First is the length, and even in this you note that you spend too much time explaining something that you've worked on. I think the length was partially unnecessary and not just a reflection of me not being your target audience (I assume). The second is that you come across as exceedingly arrogant. I think you are attempting to explain your background so that we understand the situation. But you explicitly call yourself smarter than the typical reader of the site that you are posting this on. Ouch! But again, perhaps this is just a reflection of you having a very narrow target audience and for them this could read like a "ah, finally someone gets it!"
I hope that you take this to be useful, particularly for when you write for a wider audience. For what its worth, my mental post it note has you labelled as a user that I should pay attention to. I say that since I kind of suspect that you already know everything I just mentioned and aren't bad at overcoming these in other situations, but thought this worth saying explicitly given the context of trying to improve.
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Thanks very much for the feedback.
What would you cut out? The reason that I went into so much detail is that the information would have been so crucial for me personally, and that other readers may have similar issues.
I'm curious why you that I'm not part of your target audience – feel free to elaborate.
I might be oblivious, but I don't see where I called myself smarter than the typical LW reader ... the difference in intellectual sophistication between me and the average LWer comes primarily from how I spent my time growing up, not from a difference in innate ability. I spent tens of thousands of hours optimizing for developing my mathematical ability and epistemic rationality, and as far as I can tell, most LWers haven't.
My subjective sense is that what I'm saying is analogous to doctor saying "I spent 15 years training to be a doctor and practicing medicine" in response to somebody asking "why do you think that you know more about medicine than we do?"
I know that I'm coming across arrogant, but I don't have an intuitive understanding of why I'm coming across as arrogant. I'd appreciate any insight and/or suggestions.
I'm not sure we understand each other here, but I'm assuming you want to know why I do not consider myself part of your target audience. I don't have a concrete answer here, it's just that I read this and thought it didn't apply to me. I had some of the same difficulties as you, but not in a way that I feel your advice would have applied or still does apply. I can think of a friend for whom some of your advice would probably apply, though, and imagine you are targeting him and not me.
This is what I take from: " I almost never went to Less Wrong meetups, because I had already thought about most of what people discussed, so that it was more efficient for me to learn on my own." and similar comments. I can see how you would take it as saying that you simply have already thought about that ahead of time and so you're not claiming to be smarter. (I've tried to explain that circumstance to people before myself.) But most people will take that to mean that you think you're too smart for them. Other comments suggest that this "most people" does not transfer to "most LW readers," though, so maybe I'm misplaced. This is also something that I thought could have been left out entirely. If you had to include this I would have suggested mollifying it a bit: make the problem seem to be yourself rather than others. Something like, "I struggled to find common ground to talk about even during LW meetups." This loses some specificity, but I'd play around with that kind of phrasing where you claim the fault is your own.
Another example would be something like describing yourself as "The guy who has deep insights but who doesn't get anything done, because he he's socially dysfunctional so nobody listens to him". This is a pretty big humble brag. If I wanted to say that to a typical person I might have said, "The guy who doesn't get anything done, no matter what insight he has, because he's socially dysfunctional so nobody listens to him." It's more cautious and definitely doesn't claim "deep insight" which is a phrase I'd reserve for describing someone else. You leave it up to the reader exactly how insightful you are implying yourself to be. It also changes the focus to your difficulty rather than the strength (which is demoted to an aside). I'm no writer though, so take this specific suggestion with a grain of salt.
Similarly for claims about deep insights from machine learning. Make the focus the difficulty you faced, not the deep insight you had. Maybe say, "I struggled even more after picking up machine learning jargon and modes of thought which I couldn't well articulate, even to my close friends."
Others have pointed out that you're also very humble throughout. I agree with them, too, and admire your ability to spell out your own failings. But people read "humble brag" mixed statements as primarily bragging. To you, it might seem really really significant that you were struggling, but that's not the focus people will read.
For the doctor analogy, I agree that that's what you're trying to say and I think you partly succeeded at that on one level. But on the other level, people will be turned off when you express expertise in areas where you do not have an obvious qualification. A doctor has a diploma to point to, and people are okay with that. A self-proclaimed student of medicine who had spent 15 years learning privately would be treated quite differently form the doctor. It's not a fair world! Had you been more specific I also might not have taken it like that, instead it seemed to be a blanket statement, like how an adult might say that all conversation with a child is tedious since the child just hasn't had any exposure to interesting ideas. Regardless of how factually true that is, the child could feel slighted.
This is all my take. Lumifer's response seems reasonable, too.
What would I have eliminated to make it shorter? It's a matter of taste, I suppose. I might have removed most of the part about how you grew up. I felt it could be summarized in a few sentences. But looking over this a second time, I think I may have clumped a lot of the things I thought came off as "arrogant" under the tag of "needs to be removed" and then interpreted that to mean that the article was too long. I'm sure it could be tightened up, but other than that growing up section there doesn't seem to be anything major. So take that complaint of mine lightly.
Ugh, I need to take my own advice and not write so much. Easier said than done.