I think that you and some of the others might be interested in my story, if it doesn't make you too uncomfortable. It's not a neat and tidy moral fable that illustrates how you can succeed if you do the right things and vice versa.
I'm currently homeless. I chose this about 7.5 months ago, even though for part of this time I was employed full-time at $18/hour. I wanted to help my ex-wife with her rent after I moved out, and to put the rest of my money toward dental work, health care, health food, and relocation. I graduated with Research Honors with a BS in Electrical and Computer Engineering from a top university in my field in 1995. As an embedded software engineer at a fast-growing wireless telecom company, 1995-2000, I earned extra stock options for my performance, such that in 2000, when I resigned, the current valuation of just the options I forfeited was around $500,000. But now, now I am homeless. And I am finding the stress of it is dragging me down, such that it may become a vicious cycle if it isn't already.
A story like this tends to make people uncomfortable; especially, people seem to scramble to tell themselves that they and their loved ones cannot possibly share such a downward trajectory. I must have done some really stupid things in order to deserve this, right?
In a nutshell, I think that I did make some less than wise choices, but possibly not any of the ones that you are imagining. I did not develop a drinking problem, gambling problem, or any of the other moral faults that most people imagine. I also did not have a bad work ethic. In fact, one reason I resigned was that due to the huge incongruity between my work ethic and others judgments of me as they tried to figure out what I had stopped accomplishing much. Frankly, it hurt my feelings, and I was tired of being insulted, although I understood where they were coming from: Unless a medical professional labelled me as sick, a smart guy who has ceased to perform well must be lazy, right?
I could make a case that my work ethic was too good: I refused to be paid more than I thought I was worth, and I also decided at some point to focus on doing whatever work the market was under-valuing. This could have been good for humanity had I succeeded (it was a mooonshot I was attempting) but it was bad for me personally.
What happened to me? I would say that gradually and in stages (starting with a dad with poor anger management and moving 12 times by age 12, across states and internationally), I developed some kind of trauma syndrome, in the direction of PTSD if not that per se. If you have read about trauma, you may know that the effects can come on cumulatively and gradually. A few head injuries along the way may have helped, though all of them happened before I entered university.
This is also a story about the failure of health care. When the actual care didn't fail, the marketing of it did, such that it took me forever to identify trauma as the central problem. Before that I thought it might be "Chronic Fatigue Syndrome," but this didn't quite fit; my fatigue wasn't constant but more mental and triggered by challenging mental tasks; eventually I learned that CFS and Fibromyalgia are highly correlated with trauma and can be caused by it.
I am working on writing something about this, telling the whole story, or as much of it as can helpful to readers. I also seek worthwhile venues in which to publish it. The tension I sense is between finding sufficiently thoughtful readers and finding readers who won't be so sensitive to my horror story that they put on their protective blinders. I need readers who are willing to read honestly.