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1) Graduated high school and went to college in the late 90s, started teaching at the college level in mid-2000s, still teaching at the college level.
I would say that in general I didn't notice much of a difference between when I went to college and when I started teaching at college. I went to a state school, I now teach at a (different) state school. Students generally got done what they needed to get done, partied, enjoyed chatting and having fun in the classroom, and more or less seemed to live their lives fairly similarly to how I did.
The last few years have been different, and I'm not entirely sure why, and it is specifically the last few years when the shift occurred. I've spoken with numerous other teachers about this, and everyone I talk to about it that's been teaching for a while seems to have noticed.
As people have noted, students now are more diligent. They work really hard, they're polite, quiet, but are woefully unprepared for adulthood. Yet, they're almost to the last all fairly "corporate" and "professionalized." They act like they are all intending to become middle managers. The idea of college education as anything other than (incredibly expensive) job training is lost on them -- likely due to that "incredibly expensive" part. They diligently do busy work, but when asked to do creative, novel, or independent work/analysis, it's like that screen Chrome browser gives you when it crashes. They're also less anti-authoritarian than I've seen in the past. This is helpful for classroom management, but I worry about a society of people who unquestioningly do busywork, can't think independently, and blindly listen to authority.
If you think it's just me, all teachers teaching incoming freshman last year had to attend a lecture series given by a couple of the deans regarding the demographics and habits of our incoming freshman.
Basically, the takeaway was this: We should not expect students to be able to pay attention in class. We should not expect students to be able to socialize easily with their classmates. We should not expect students to be able to understand and/or figure out a syllabus. We should not expect students to be able to manage their own personal affairs outside of the classroom. We should not expect them to be able to self-task in terms of research/self-education. We should expect more phone calls from parents, more parental intervention, and a heavy reliance on parents by our students who, we were informed, are likely texting their parents during and/or immediately after classes if they get grades they feel are unfair. Most of the "we should not expect students to be able to do X" comes from research that the deans cited (I don't remember if it was from our university or published in a journal or what) that shows that most of those issues stem from that extreme reliance on other people, typically parents for younger students, through all of their K-12 education. AKA, their parents did so much for them down to explaining class expectations and how a course works (syllabuses), that now that they're expected to do it on their own, they can't because they've never really done it.
I think the deans maybe were a bit hyperbolic, but most of that does seem to be true for a lot of students now, and I will say this: until three years ago, I had NEVER received a phone call or email from a parent regarding their children's grades and/or academic performance. Since 2014, I have received numerous phone calls and probably a half dozen emails.
You want to see a helicopter parent lose their shit? Explain to them that their children are legally adults and due to FRPA guidelines, I can't discuss their grades or academic performance with them. So, I don't fault my students necessarily, and I don't know if this is a long-term trend or not, but I definitely have noticed a pretty significant change in my students over the last few years. I also get the sense that they may know that there is something different about them vs. previous generations of college students, as I find them expressing concern about themselves and their classmates. They say things about people struggling to look each other in the eye, or make small talk, etc.
So, anyway. tl;dr -- students are politer and more diligent but have become worse at adulting and being independent.
2) Everybody is going tech so I'll go with cultural.
All teens rebel. They all think they have it right and the grownups have it wrong... but they show it differently.
In 97 the prevailing word was Anger. "I HATE the way things are.." Kids were harsher. Meaner. Being nasty was the way to show you're cool. I saw a lot of kids get their kicks out of breaking the Santa illusion for grade schoolers for example. 17 kids are much nicer to each other. Think of the music of the time, Smashing Pumpkins, NIN, and the like. "In spite all my rage I am still just a rat in a cage"
In 07 the word was Mope. Kids were softening up, being nicer to eachother, but also getting more into the "Sadness is beautiful" kind of thing. They weren't angry at the adults so much as they just wanted them to go away and hide into their hoodies. "Leave me alone to my solitude." Consider the way Emo was huge at this time.
In 17 kids are MUCH nicer to each other. They're kind to young kids and friendlier in general... but there's this strange undercurrent of competition to be "The Most Good Person" which leads to the weird "Yes Mayonnaise is a gender if that's how you identify" kind of thing. In '17 kids want to explain to the grownups how they're all bigots. They also handle failure FAR worse than previous generations. '17 kids try harder and genuinely want to succeed in ways that the '97 kids didn't. In '97 you were cool if you avoided working hard and didn't care if you failed... but '97 kids also recovered from adversity faster. They didn't bruise as easily. They were harder, meaner kids, but also didn't quit as easily and thrived on constructive criticism.
Now there's bits of each of these personality types in every year. There were nice kids who were also soft in 97, and there are mopey emo types now... but the prevailing culture shifted these ways.
3) my dad taught middle school from 1968-2004, when he retired i asked him what changes he saw in students from the beginning of his teaching career to the end. he answered; "the kids never changed. a teenager is always a teenager. the parents however, changed dramatically. they used to respect teachers and side with us in disciplinary matters, but now they think their kids are perfect and we are wrong. glad i'm getting out before it gets worse."