My philosophy in life is that things don't need to be complex even if the underlying things are. Usually by investing some taught into things you can find a simple way to make it work. You can't be the best at anything by opting for the simple solution, but then again, why would I want to be the best?
I know things around me are complex but there is usually a way to simplify them. It's true what you say. Things don't always work as they used to. You can't expect to run go to school and further your education and end up with a job. Not anymore at least. You can't just buy a house as an investment and expect to be rich. You can't just go on like your parents maybe did.
But with all of these things, there is always a way to turn a complex thing into a simpler thing. If you can't you didn't think it through. I like the quote by whom ever (don't know who originally said it): "I always hire a lazy person, they'll find a simple way to do things". I associate myself with that. I tend to be a bit lazy, but not in the sense that I never do anything. I just find the easiest ways to do things to a level that satisfies me. There always is a simpler way.
You can go to school and make it land a job for you, but you need consider certain things like: "what should I study?", "what is the future going to be about", "do I need this?". You can still buy a house as an investment, but not the way you might think. You need to calculate the savings you generate by owning the house instead of living on rent. Or better yet, rent the house and earn income on it. It really isn't that complex.
Finally, when it comes to retirement, if you want to retire, invest and you can do that early on. If you think it will take a long time to retire, find something you enjoy working with. This isn't really overcoming the complexity, but it definitely makes it nicer.
I think that is very true, although the world is complex, navigating it does not have to be a complex endeavour. But as you said, you have to invest the time to think things through.
Many people still follow the auto pilot of old assumptions to go through life with increasingly poor return on investment...
Like Darwin said: Survival of the fittest. that does not mean the strongest or the smartest, but the best adapted!