Would help to summarize these pieces, say what you find compelling & anything you disagree with.
(not all of us want to wade into a lot of videos, so if there's more reason to...)
I mean, off the bat - Gen-X was promised a continuation of the post-war boom + hippie idealism and instead got malaise & Reagan selfishness. But we still cope. But there certainly is a heavier feel of monopolies that keep a newbie from making traction or for paving your way outside a mega-corporation. But that still affects more than Gen-Z or Millennials. "a medieval world instead" sounds pretty hyperbolic. Make it better, goddammit. My generation hacked computers - made some things better, some things worse. This/last generation can hack health & the mind directly. Fixing property ownership & local government's another issue, but still - these are life's problems to tackle. Some is overhyped, but when I read that Delhi's swamped in deadly smog, I can sit there & think "in a decade this will all be fixed with electric cars", in a large part due to Elon even if others are overtaking him & will deliver the majority of those cars, infrastructure,new battery tech. I lived in LA when it was horridly smoggy - we shipped our problem elsewhere with Chinese offshored production (of course for them it's on-shore). But their millennials got continual growth, move to the city, worker bee lifestyle, and a step out of feudalism. 1.4 billion Chinese in a much better space. Add to that other Asian countries including huge India - not all fixed, but improvements & a way out.
But Covid's also painted a target on the health system - it's not very flexible, it really is old school, we can make life much better for everyone with a revolution, including in psychological care. 
https://www.theatlantic.com/health/archive/2021/11/health-care-workers-l...

It gets harder (science edition)

Say goodbye to low hanging fruit

https://www.salon.com/2021/11/26/is-science-stagnating-the-great-stagnat...

Re: "turning medieval" and the author's diatribe about "liberal hysterias" of "racism, global warming and pestilence",  i think he's full of shite, and he exaggerates where he accuses others of exaggerating.

1) we have a pandemic - it goes up and down, but it's poked huge holes in our supposed health expertise - part by our stupid ingrained tribal politics, part because we're just not that good still - we took the low-hanging fruit, but left a lot of the more important problems & logistics & understandings behind.

2) global warming - we've hardly done shit to mediate global warming. Installing a bit of solar & wind is great, but it's way down the critical path from where we should be to limit effects on polar ice and extreme change of climate. While Electric Vehicles are promising, we're talking 10-15 years away for the transition to complete, and that includes wiring up the outback, be it Australia or the Amazon, Central Asia or Africa. Once you take the gas pump & canister out of the equation, there's a whole different operational mode that the world has to adapt to.
And that doesn't get into heavy machinery (running on electricity? how much torque can it generate for heavy loads?), or airplanes (how do you substitute electric for powerful jet turbines?). And if we turn around and generate the supporting electricity from coal, we've done nothing for global warming.
Besides global warming, there's global smog, such as what's attacked Delhi lately - many cities are drowning in smoke. And relying both on electric cars & cleaner smokestacks to do it. 10-15 years can leave a lot of damaged people behind.

[Germany's/Merkel's decision to turn off nukes before solving alternate energy is one thing leading to their need for that controversial Russian gas line. Yep, can't take energy independence out of the equation - plus what month will Russia threaten Ukraine's/East Europe's energy again? taking bets now.]

3) racism - get real. We are half enlightened, half Neanderthals in our evolving on race, and for those of different races there are a ton of everyday hurdles that do show up more often than for white folk, at least in our culture - if we're in Africa or the Mideast or Asia things can be reversed - tribes often discriminate against non-tribe members, that's still part of our DNA. Sure, some people cry too much about racism in everything, but there are huge structural problems that remain as well. It's obvious the GOP writes voting laws to disenfranchise blacks in numerous locations (absence of voting booths in black districts, etc.). We have more quotas for minorities, but we also have screwed up schools in heavier minority areas - it's 2021 and we still seem helpless to make a real difference - to get say 80-90% of those students reasonably educated and productive? Instead it's always social problems social problems. Blacks are undoubtedly going to draw more attention from police, and it's harder to get through adolescence without something seriously bad happening - due to bad decisions & pressure from others, as well as unwarranted profiling and an often unfair system. Call it 30% slanted and it's still a pretty big thumb on the scale. We can do better. That's not "hysteria" by any means. Of course that also includes controlling guns - when i was growing up I thought The Man was sending drugs to the ghetto to kill people off, but now it just takes a bit of firepower. Pretty horrific. And certainly enough blame in many directions, but it's something to solve, not just banter on about. That is perhaps the only "Medieval" aspect to the situation - that a continual subclass of dog-eat-dog criminal behavior rules large segments of society, and we can't seem to fix much of anything, generation after generation, it only gets worse, even as some educational and acceptance improve? Makes little sense.

But yeah, woke speak is an easy target, but it's a bit like the #MeToo craze of 4-5 years ago - it will get a lot of attention and then settle down into a more normal state, or perhaps too little (it's still galling how "Take a Knee" based on police shootngs was so offensive to so many of our snowflake citizens - even now there's a big self-defensive movement, "Racist? we can't be racist, blacks are not repressed, everyone has the same opportunity". Maybe in a San Francisco startup with 20-somethings around foosball tables, but there's quite a bit of racial & gender (& age) discrimination that goes on in the daily workplace - even IT's "cultural fit" is also code for "weed out the extreme ones". Now look at the long climb for the kid from East St. Louis or Anacostia or Algiers. Doable for some, but certainly a huge challenge.

Ok, I broke down & watched - tell me the inherent difference of the oil embargo, the collapse of the Rust Belt with Carter inflationary malaise (yes, he helped Reagan by being the adult), the dot com bust, and what not?
I know the Jetsons promised us flying glass cars & a robot greeting us with martinis coming in the door, but I'm not sure any of us believed it, just like earlier generations didn't believe in War of the Worlds or what-not.
By brother graduated with a prime degree and spent his 1st professional year making Xerox copies. I recall near 0 jobs advertised, and that was in the days where you had 1-2 classified sections to skim through & that was it. Everybody started at the bottom, just like we all had crappy pizza jobs in high school and mowed lawns before 16. I don't recall a huge number of guaranteed jobs for early graduates, except law students from cherry schools in the best of years. [yeah, Wolf of Wall Street is our real future too, amirite?]
The idea that the internet has changed that much - well, we've had movies for a hundred years to show these dance to success tales/chorus lines, and then there's TV smiley personalities, and all these game shows - you too are a winner! and whatever other fantasy football people are peddling for whatever generation.
The only real difference I see in all of this was 1) the Great Depression was real shit, that led into the largely shittier but romanticized World War II, so it's pretty amazing to hear anyone complaining about oh, a recession & a pandemic in 11 years! [try World War I where much of Europe had a huge bloody war & then 2 years of the more brutal Spanish Flu]. and
2) after World War II, the US economy was pumping at full speed, industry successfully transitioned from wartime footing to consumer goods, all the returning soldiers got GI Bill with cheap housing loans and school benefits, while Detroit cranked out cheap cars and builders stacked up cheap suburban housing everywhere, and since Europe was still destroyed, they could rely on a decade of heavy exports to make life wonderful.

But that post-war bonanza was back in 1945. seventy-five years ago. Who promised everyone Camelot would continue indefinitely? If you graduated into Korea or Vietnam you didn't have all those "career opportunities" unless you didn't get your dick blown off and made it back in one piece, including your noggin'. If you were female in the 50's, well, you mostly went for that housewifey thing and gave up those amazonian Rosie the Riveter factory wench aesthetics, and instead worked on the color combo for the living room set, and dreamed of linoleum.

Look at the whole British ashen horizon of the 70s - much of Bowie's apocalyptic vision was based on grim factory realities and an economy in eternal doldrums - Britain not being much better off than East Germany. Punk was born.
Sure, make things better, but this illusion that we all thought stuff would keep growing, that we'd flourish without effort, that we could just find our chosen field and push on, that's pretty delusional. We've know for decades that the age of the super industrial titans like the Big Three, GE, IBM, and so on wouldn't last, especially once we got a taste of Japanese competition and then the shift towards offshoring - before 1990 two-thirds of the world was blocked off. Afterwards you got competition. So what do they think competition means, "guaranteed better cushier jobs"? Hardly - it means some successes, some failures, though actually usually cushier (if employed), even if not as well paid.
As for drugs & alcohol, I'd guess on average there was a helluva lot more in the 60's and 70's as well - even driving drunk used to be no big deal, and coke's been a mainstay since the 70's, while speed got half the people through exams. The bigger issue is opioids & speed in terms of improved quality  and severe use.

But yes, I understand for some these recessions have been career blockers. But even if you were a taxi driver, once Uber came along you were toast. If you sold real estate, online listings took half your business. Worked hotels? meet AirBnB. Though this isn't intrinsically different from when Southwest shook up the premium airlines in the early 70's, changing a high priced/high margin business into a cutthroat barely surviving crapshoot. Vegas used to mean a kind of luxury status - now it's Disneyland. Online trading's been heavy since the 90's, more flexible investent since the 80's - that field was going to get weeded out. So who exactly said everyone's quality of life would be better? Of course if we made wise political choices and built up needed infrastructure and resources, and big corporates responsibly helped pay for government services that filled in holes as the shifting economy moved on, maybe it'd be more like Europe...

And then there's types of jobs. We're not so much working out on the farm or in mines or the assembly line or the steel mill, and where it does, the conditions are vastly different than yesteryear - I don't believe robot-enabled Amazon warehouses & car assembly is anything close to as grueling and soul-destroying as 50 years ago. Building highways is all heavy equipment, unlike the Eisenhower years. "Fast food" is largely pre-prepared food, punching buttons, bagging stuff, smiling, not a lot of dishwork. It's a tradeoff of ease, not necessarily higher pay, not necessarily the career you wanted. If you look at all the successful co-existing bands at Woodstock and Monterrey - that industry doesn't exist anymore, nor does music radio, just syndicated hate speech. The print industry? First they came for the newspapers - now it's robot-generated content half the time. Film is all digital now, easier to fly in effects than live locations, much less time required for editing & post-production... Lawyering - a lot of clerk stuff is handled through better document management systems, search, AI/Machine Learning algorithms - the 1st year law clerk is basically operating a better, much smarter Xerox machine.

So I still don't get it. Even health is being designed for faster, lighter weight delivery of services based on more and more clever uses of technology and organizational structure. Covid gave a big push to telepresence/video conferencing/remote monitoring, but it's been in the cards for decades anyway. So why exactly is there this Millennial "we were promised" thing? It's always a new version of eat-or-be-eaten, whether with better manners or fewer.