I like Wesley Yang's writing quite a lot. As a 2nd generation Asian American (Korean like Yang himself,) I understand and have experienced quite a lot of his pain. However, I think he and others somewhat misattributes the origin of his/our pain. I'm more inclined to think that a lot of this pain comes from how we are raised and an impedance mismatch between the "American dream" as our parents understood it and the dream as it is (to be fair, he acknowledges this is a possibility.)
For example, I think the stereotype of Asian men being effeminate/sexless robots is largely a byproduct of our childhood upbringing. In my childhood (and in the childhoods of most of the 2nd generation Asians I've met) dating was strictly verboten and generally seen as a waste of time that could have been spent studying. Even in young adulthood, dating is frowned upon by most 1st generation Asian immigrants unless you're explicitly looking to get hitched. Obviously, when you raise an entire generation of people this way, a large % of them are going to grow up to be sexually awkward and therefore unsuccessful in the sexual market.
I'm aware of the data drawn from online services that show that Asian males are the target of some unfair prejudice. I'd respond to this by saying that obviously online dating brings out the "worst" in people. Given the sheer number of available "mates", I'm not surprised people lean on racial stereotypes to help filter their inputs on such a platform. And if I'm being honest, yeah, a large number of us Asian males are pretty sexually awkward. If we're not, it's almost certainly in spite of our upbringing.
I'm aware that this is anecdata, but after some practice (really just putting myself out there enough,) I haven't had any issues dating in an in-person format. I'm actually inclined to believe most people are willing to give anyone a fair shake (presuming some base level of sexual attraction) after getting to know them a bit, though this assumes that you're comfortable enough with the various dating rituals to not scare anyone off (which I suppose may be a tall order if you were raised in a way that prohibited the necessary practice.)
With regard to being passed over for workplace promotions, Asians are raised to be deferential to authority. The cultural norm is basically for our parents to be regarded as dictators within the home (for better or worse.) Moving up the corporate ladder isn't just the result of "hard work" per say. It takes a certain amount of arrogance and disregard for your "superiors" and peers to engage in the kind of self-promotion required to move up the ladder. Yet again, if we're successful in this domain, it's in spite of our upbringing and not because of it.
If you've ever read Venkatesh Rao's essays about the office according to the office, you'll be acquainted with the notion of power talk. Asian Americans are not typically raised to understand this particular game and there's little room to practice this growing up when your parent's rule within the home is as absolute as it is. As Yang puts it, this requires a certain level of "calibrated insouciance" Asian Americans just don't grow up learning. Once again, if we learn to play this game successfully, it's in spite of our upbringing.
From an Asian perspective, White children appear shockingly disrespectful to their parents. Now being a bit older, I've come to believe that this is up to a certain point a selective child rearing strategy. Asian children are treated as if they have no table stakes 100% of the time with regard to negotiating with their parents (there's basically no negotiation ever.) While this does lead to a certain "harmony" within the home, I don't think it teaches people the skills they need to be fiercely self-advocating when they grow into adults. The American economic system doesn't reward meekness in anyway (I can't be strong enough on this point.) So to me, it seems counter productive to be raising meek children if the desire is for them to become competitive at the highest levels. Our identities are honed on conflict, and it's also through conflict that we develop a set of values and the ability to make value judgments about when it's when in our interests to fight or retreat. Our 1st generation parents aversion to conflict within the home I think has raised us to be overly meek in the outside world.
With regard to the lack of Asian CEOs despite disproportionately high Asian representation at elite universities, Asian Americans are raised to not be risk takers. There's honestly a certain amount of cultural distaste for risk-taking and there's huge social stigma attached to failure in this domain. Once again, if you observe successful Asian Americans in this domain, it's because they've overcome their upbringing and learned to become calculated risk takers.
Yang also mentions this notion of "pumping the iron of math." Even in the educational domain, I've noticed a lot of Asians prefer to substitute repetition and rote learning for time spent actually thinking about and understanding what they're doing at a deeper level. This kind of practice is useful to a point, but unfortunately puts a ceiling on how far you can progress. This is something that was particularly painful to me in particular. I spent a lot of time laboring under the delusion that there was a "right way" to do most everything, if only I could find it and practice it enough. Beyond a certain level of prowess (surprisingly early sometimes), you find yourself "trailblazing" for lack of a better word, and this sort of mentality can only get in your way.
I know this is an uncomfortable discussion because it raises the specter of "cultural superiority." To be clear, I'm not arguing here that Asian American culture is inferior in any way, only that in some respects it might be maladaptive to the system we find ourselves in. In a lot of ways, I think our parents have a major blindspot in that they want us to go farther than they did, using the same maps and tools that they did.
I think what our parents were blind to was the fact that there are a lot of "hidden" games that you need to learn how to play to be successful in this society, and that learning these games isn't something that's surmountable by hard work alone. As much as we like to pretend otherwise, societies are a lot more than just their laws and institutions. White folks in this country have had their hands on the levers of power for a while (for various reasons,) and as a consequence, their children are able to learn the games they need to know to be successful in this society from their parents and grandparents. Most of us are still only in our second or third generations. We're obviously comparatively on the back foot in terms of what our parents are able to give us in terms of the cultural knowledge necessary for success in this particular iteration of our society.
Again, to be clear, I'm not arguing that this situation is "moral," just that in my opinion, it's pointless to be bitter about it. If we want to go farther than our parents, I think it's clear we won't be able to do it using all of the tools they tried to give us.
Obviously, there's a larger discussion here about whether or not this situation is moral in the first place. I'm inclined to think not, but I'm also of the mind that it's not much use to be bitter about the fact. I think we'll change the situation faster if we learn how to play the games we don't understand and are able to get our hands on the levers that move the media, politics and business. In many ways, I think as a cultural group we should be looking to the Jews as an example. Despite being so aggressively pogromed over the centuries and despite there being so relatively few of them, they've managed to become dramatically overrepresented at the top of basically every major domain of human endeavor.
To finish, I don't think there's anything wrong with our faces as Yang conjectures. I think we can learn the games we don't know how to play yet and hopefully by doing so make a world that's a little kinder to our children and grandchildren (not that the world is particularly unkind to us in my opinion.) It'll just require some tweaking of our cultural values and maybe rejecting some of the tools and maps of the world we were passed from our parents.