These kinds of essays resonate with me but there's always something about them that seems really off and misguided at the same time.
The survivorship bias you point to is a big part of it. Reading the biography of Carnegie, just as one example, strikes me as kind of egregious because it quickly becomes obvious he was part of a child labor system and by counterargument succeeded largely because he was one of the lucky poor given access to private education by a wealthy benefactor. You could just as easily turn Carnegie into a counterexample, of what happens when you give a child an education with lots of attention. He also happened to be in the right place and right time, in the railroads just as they were taking off.
The focus on the schools too seems really misguided to me. Most of the problems with society today, in my opinion, are due to all the formal roadblocks placed up by bureaucratic red tape, instantiated by the labyrinths of government or private human resources departments.
There are just so many things that require such and such degree, or such and such experience, not because they're actually necessary, but because various legalistic bureaucracies require them. Some of the examples in the essay could happen today, but most of them probably not. The essay seems to quietly acknowledge this but then turns attention away from it, probably because it undermines its thesis.
In my own career I've heard lots of stories like this from the past, both close to me institutionally and more distally. People just sort of showing up somewhere and chatting and then getting a career because they came there to do the work, were respected on the basis of conversation, and had a path forward. None of that would happen today. There would be rubber stamping required, certificates and degrees in a specific field or subfield, with no attention to whether or not the person has the actual ability and background in the area to do the tasks involved.
Schooling today I think has problems, and I agree with the premise that doing things is important. But I think schools teach to what is out there in the world, and students are doing things in school curricula all the time with no acknowledgment later because you're seen as commensurate with a degree. It's not a problem with schools, it's a problem with having vocational paths with opportunities be open to people who have the skills and abilities, but just don't have quite the right credentials or connections. Maybe it's always been that way, but something about today's society makes the examples provided in the essay seem irrelevant today for all sorts of reasons that have nothing to do with the schools themselves.