I am a bit conflicted about this. On one hand, I agree with some of what you said, for example how having to work for things gives a much greater sense of accomplishment. This is good. On the other hand, you used the word “Brutal” in your title, which makes me want to point out a few things to you.
You mention some benefits of wealth, but don’t mention all the zillion other ways that wealth provided invisible support, from health care, transportation, free time, and just never having to deal with all the problems poverty brings. These things suck time, energy, and break other things in so many other ways that you just have no idea about. Relationships. School work. Clothing! Nutrition! Health! Its the old poem about how the lack of a nail leads to the kingdom being lost.
I grew up middle-class with few of those problems. My father had similar ideas to yours, that things should be earned. However I had to mow the lawn for nothing, and had to get a real job to earn spending money. Paper route at 12, spent a summer picking tobacco at 16, bussing tables, washing dishes, assembling bikes, stocking shelves, pumping propane, etc. all before I finished high school. Trust me, rich or poor there were no excuses for failure for myself or most of my middle-class friends either. Did you think we could say “I dropped the winning score, but that’s because the ball was old and too smooth”?
Drug and alcohol problems have no uniqueness for the wealthy, and I don’t get most of your other points either. Do you think suicides and overdoses are only for the over-privileged?
It seems that the basic point of your story was how tough the shock of voluntarily going from privileged living to less-privileged living was. Yet you also acknowledge that you could have bailed on it at any time, so never was there any actual fear in you. Then you chose a life based ‘only’ on your own accomplishment, the end. You are a self-made man! Never had any help from anyone! Did it all by yourself! Not like those rich kids with all their parent’s money, and not like those lazy poor people who just don’t have the drive to be a pro gamer…
My advice, take the word Brutal out of your story title, and write it again with some more thought into how you actually suffered.
Sorry if this sounds harsh, but the context of our current world political climate makes it seem important to me.