To clarify a couple of things: First, I was a full-time grad student just over two years ago. I'm 28 years old and therefore right at the cutoff between the Millennial generation and Gen Z. I was raised on a steady diet of social justice, delivered at all levels of my education from my teachers and from school programs. Second, I don't mean to suggest that my boss was cruel or apathetic at all. It occasionally felt that way, but I think that my frame of reference was warped, because I wasn't oriented properly to the way the world works.
Well, you did suggest that. So good you clarified. But what you describe isn't really abnormal at all. It is just part of having your first job. Many not for everyone or even most. But for enough people. University isn't supposed to learn you 'how the world works' or how to manage a demanding job that requires an advanced degree. You only learn that by experiencing it. And if a student or as a new employee you somehow has a warped expectation and needs an 'attitude adjustment', it is really not so easy for a teacher or boss to consciously intervene and fix that for you. Maybe your boss was actually a very good boss, aware of what you describe, and actually acted the way they did to help you. But usually, people are much more preoccupied with their own little world.
I have had students who were just a couple years younger than me who to me already seemed to have a different attitude to myself and my fellow generation of students. And I have had some who seemed to make things unreasonably difficult for themselves in a way I couldn't understand or relate to. And you don't know if they are just having a bad day, are on the spectrum, or have some attitude problem. It is really challenging to step in and criticize them for that. You'd have to build trust for that first. My point is that just giving them a hard time 'so they feel until they learn'. is not productive. I could have stepped out of my way, not said anything, and thrown up artificial hurdles for this student so they would finally see how 'silly' their way of thinking was. But you don't know how they experience that because they are also already in their normal learning curve.
The student may learn what they are supposed to learn in the course I give, actually have an attitude problem, and they may indeed hit a wall when they leave university and go out in the real world. And they either adjust, or they don't and are then not able to perform a job that matches their advanced degree. Which would be unfortuonate. But these more meta life or people skills are really challenging for people to learn.
I had thought that my problem was my job, so I did change jobs in December of that year. I quickly discovered I was encountering the same problem at my new job, even though my new boss is unusually patient and supportive. It was at that time I realized I could fix most of my problems with a simple attitude adjustment. That's not to say that it was easy and immediate, or that I don't sometimes slip back into my old habitual way of thinking, but even a partial and imperfect transition to an attitude of personal responsibility has made my life immeasurably better.
So actually your old boss being 'apathetic and cruel' (your words, though clarified) didn't work for you, but your new boss 'unusually patient and supportive' did. You could say it was the 'tough love' approach of your old boss together with your new boss that did it. But things could have turned out the same way with different experiences.
Would you really say that something about the education you had being less a 'diet of social justice' would have prevented your challenge and completely prepared yourself 100%?
Or where your 'warped frame of reference' came from? I don't mean to pry, but since you are using yourself as an example. I just don't really see how your story is an argument against 'woke education practices', if it was at all meant that way.
Failure can be a good life teacher. But deliberate building 'failure experiences' into an education program is really not something anyone in charge of education programmes would argue for. Sure, if a student finds the course too easy you should find a way to challenge them more. But that is only natural, though sometimes not possible because of the number of students and the workload. Arguably, it is better than someone faills on their face hard when they are 17 years old then when they are 38 because at a younger age it is much more easily to adjust. And a good education program has nothing to do with removing the consequences of real life. So I don't see how you can make education 'less soft' to 'build more character'.