I believe there is a difference between going ultra-light and being ultra-dumb. I found that, when I started camping and hiking, I carried everything but the kitchen sink. After a while I started getting lighter and lighter. Not as light as some of the guys who do a month of camping with just a daypack, but I know what gear I use, what gear I don’t/didn't ever use (and therefore could get rid of), what gear I could make lighter or more compact, and what gear I wouldn't change. Because of that experience I can get my stuff down to the basics and better adjust (a head of time) for what I plan on encountering while on my trip.
I think the problem is, a lot of these guys just look at someone else’s list of ultra light gear, assemble a similar pack, and then go out and plan on being ok because they pack the same gear an "expert" does. Fact is, if I handed someone with little to no experience my gear and told them to go out for a week I doubt they would do very well. All the gear in the world wont save you if you can't use it to the fullest. I think the best way to learn is start carrying as much stuff as you can handle that will ensure comfort and safety, then over time (with experience garnered in a relatively controlled setting) adjust what gear is carried.
Now, I do think we have all done stupid things or tried to go out with a little less gear than may have been required (or just forgotten something important). It’s part of learning. However, when I adjust my gear I always test it out in a controlled setting (where I can reach my backup gear) first before I plan on doing something heavy duty.