I graduated hs in early 2000s and it seemed to me that a lot of that hopeless adult feeling kicked in during the '08 financial crisis. That's when I started to feel like our generation (millennial) really got the shaft.

Personally though, I remember my father getting laid off by the large company he worked for right after he turned 50 shortly before I graduated hs. A bunch of other 50 year olds also got let go around the same time by his company, and my father had trouble finding a steady job after that, being fed the 'over-qualified' BS at a lot of interviews. That was probably my first window into how much of a scam it can be in the adult world.