Don't discount that the world was a more dangerous place to grow up 40-50 years ago. The "boomers" and "gen-Xers" that made really bad decisions just aren't around to talk to anymore.
But I do get what you are saying. The level of "success" that boomers and gen-x achieved required less effort that it would today. However, I will also say that the "bar of success" has moved higher as well.
"Success" in the 50'-60's was a car in the driveway, a 3/2 or 4/2 house 1600-1800sq ft home, 2-4 healthy kids, a single "big" 16-19" TV, a console radio, one phone and nearly no other electronics except for small kitchen appliances.
"Success" in the 70's/80's was the same 1600-1800 sq ft home, but with a 2 car garage with 2 cars in it, a microwave in the kitchen, a VCR and an ATARI (with a dozen or less games) for that old console TV, a 2nd small TV for the kitchen a couple of "Walkman's" for the kids and a "rack" stereo system, and a couple of ATV's or dirt-bikes.
Fast forward to today and success is 2400+ sq ft home with 3 car garage full of boxes of junk, 4 cars parked outside, a flatscreen TV in every room, every member of the family has their own laptop/computer, cell phone and a myriad of other electronics. There are at least two different console gaming systems (with dozens of games each) that get updated every other year (if not every year).
The "system" that exists has turned every family into a consumer of products that are 100% unnecessary while at the same time convincing said family that said products are 100% necessary.
Move the bar back down to the 1970's level of "success" and I think you'll find the current generation much closer to "success" than they currently feel.