In my article The Status Trap: The Middle-Class Pretending to be Upper Class I explore the problem of the middle class wanting to prepare their children for ascension into the upper class, and mostly only ending up wasting their money. Even though the money for expensive private schools and universities may not be worth it, they do fulfill a certain role, namely shaping behavior and mindset of students. If you do not have elements of this mindset, there is a good chance you will not advance meaningfully in your career.
My view is that there is increased competition for resources in the West. The middle class is under attack, which is arguably why these people are so willing to invest in their offspring, making sacrifices that may lead to their resources stretching thin. However, even the upper class is “downwardly mobile”, as it is politely called. The average son or daughter of an upper-class family likely will be worse off than their parents. This is particularly true of the large fraction of the lower upper class. They do not command large fortunes. All it takes is the 100-person company they own falling on hard times, and within a few years their life of luxury may be nothing but a distant memory. A common pattern there is that there is one heir, who may perhaps even take on an active role in the family business, and the others may have to find other ways to support themselves, of course with significant financial support until they have found there footing, and often even beyond that.
I have encountered quite a few people from pretty well-off families in the corporate world. However, they did not sit at the top of the hierarchy and instead have to work their way up like everyone else. Some of them have character traits that may make it more likely to advance. You cannot acquire them on your own. Instead, you need to be in a particular environment. I got a bit of that when attending selective universities. One of them in particular stood out as it has a reputation of being one of the most selective in Europe. It is also a pretty expensive place, so you can imagine what kind of person you encounter there. This is most definitely an environment in which the upper middle and upper classes congregate.
The big difference between studying at that place versus regular universities was that your professors did not enforce a status hierarchy. Instead, they treated you as a potential future peer. In fact, given how brand-conscious academia is, this was not just idle talk. Plenty of alumni of this university do end up teaching there or at other similarly highly regarded universities. Another aspect was that the atmosphere was supportive to a fault. There were certain expectations, but nobody was breathing down your neck. We had weekly or biweekly essays and assignments to hand in, but these were voluntary. Only the final exams counted. Most if not all students did all of the voluntary course work anyway, though. I once forgot about a deadline which absolutely had nothing do with me banging random chicks during the week. The professor of this class learned about this because I reacted surprised when he reminded us of an upcoming deadline. His reaction was to approach me after class to ask if I needed more time.
My perception was furthermore that it was difficult to exceed standards, just as it was quite difficult to fail a class. Of course, the students were of a pretty high caliber, and given the money they spent, they took the instruction much more seriously than your typical state-school student. Still, not everybody there was a genius. There were just four grades, essentially. To use the US-scale, which does not properly map to the UK-scale, you were looking at very few students who got an A, most getting B’s or C’s, and very few, if any, receiving failing grades, i.e. D and below. The messaging was that you had to really work hard for an outstanding grade but if you wanted to just do the minimum because you only cared about the brand name of the university on your CV, you could do that too.
The focus was on independence. There were very few lectures and seminars. Instead, the expectation was that you basically taught yourself anything you needed or wanted to know, and the various essays and assignments gave you plenty of opportunity to show off what you had learned, or what insights you gathered. There were limits to that, though. The worst grade I ever got was in an essay in which I wrote about IQ and its implications for social policy, which, to me, seemed like an underexplored question in academia. I was quite proud of this paper but my professor was not happy about it at all. I got the equivalent of a C-. He seemed genuinely upset with me and advised me to, in the future, not cite people like Charles Murray. Nonetheless, he offered to support me regarding topic selection and literature search as he did not want to see me repeat such a mistake.
I did not attend elite primary and secondary schools, but I have a personality trait, which I developed probably somewhat arbitrarily, that is not at all uncommon in elite circles: irreverence towards authority. In these circles, it normally comes from people having so much money that they just freely speak their mind because they know that they will not face any consequences. In my case, I am simply a pretty smart guy and I do not care much about getting the approval of others. Obviously, I am aware who I am talking to, professionally and privately, but I am very far from being a lickspittle, which I see very often from people with a traditional middle-class upbringing and mindset. Another aspect of the upper-class I noticed is to sometimes throw out big words or even puns, and cracking a joke even in a potentially unfitting context. This also fits nicely with the theme of showing some element of irreverence. At the very least, it lightens the mood.
I really do not want to give the impression that I have an upper-class mindset, because that is not the case. I lack the financial means for that. However, I understand enough of the world to realize that the middle-class socialization of wanting to fit in, check all boxes, and all that nonsense will not take you very far. This applies to my professional life as well. Multiple times, I was given certain responsibilities and chosen over others who perhaps were better qualified on paper because I had a particular attitude which they lacked. To give you a particularly noteworthy example: in my last role, my reporting line was changed because my manager’s manager wanted to directly talk to me. We got along very well, and he valued highly that I gave it to him straight, including some uncomfortable truths, whereas many of my peers were primarily concerned with pleasing everybody and fitting in. You cannot blame them because their entire upbringing was spent on practicing to jump over hurdles, however nonsensical. Obviously, irreverence is a double-edged sword. I have also had managers who told me that they cannot work with me and that I should look for a different job. I should add that these people had the typical afraid-to-stand-out middle-class mindset. By and large, though, I think I benefited a lot from elements of elite socialization, and it would be quite dishonest to claim otherwise.
So far, I have only spoken of the male perspective. I do not think that a guy can ascend into the upper class. This may only work for his children, in case he manages to acquire great wealth. In contrast, women can do that. They only need to find a rich man who wants to marry them. For this to happen, though, she probably needs to have gone through an elite education, at least for a few years. Otherwise, she would find it quite difficult to be perceived as a potential love interest. Thus, sending your daughter to study at Oxford is probably a better choice than sending your son.