I read this expecting to see some heart wrenching tale of some sort, not, "I wanted to keep up with Joneses AND do what I love, and, God darn it, if responsible people will have to be hurt so that I can have my cake and eat it too, so be it!"
Also, this man is an idiot. Tax fraud has knocked a LOT of people out of respectability. In this man's lifetime, Enron happened; insider trading has been a recurrent scandal. Also: Comparing something ILLEGAL to "almost illegal nepotism" is stupid.
Every few months, I examine my finances and say, "No. I'm not quite in a good enough position to go to grad school/buy a condo or house." The problem the author has is that they look at the END POINT ["Geesh! I'm in a lot of debt."] and try and work a solution out, instead of looking to BEFORE that end point, ["Yeah, this college is somewhere I'd like to go, but man, it's expensive. Maybe I should do research to see that, unless I'm going to a ridiculously elite school, a degree is a degree."] or ["Maybe I should save some money to help afford college/get scholarships/grant."] Or, "Maybe I shouldn't look down on technical educations and only find value in attending 'small, liberal arts colleges.'"
Also, dude, you DID win an award. You literally got the chance to go to college. An expensive chance, but one that lots of people want and never get. Instead of making a financially sound choice, you made one that wasn't. It sucks; life sucks sometimes. If you'd gone to the school you could afford, your life may have been different. But, I'm willing to bet that you could have made it work. You've been published by the New York Times, so obviously someone thinks your writing is good. You could do what probably literally millions of other writers do, take a job that helps them pay the bills while writing on the off time. Or, you could make the choice that literally makes it harder for the NEXT lower middle class or poor person to get the opportunity you had.
The problem isn't that the author came from "modest origins." The problem is that he's selfish and unable to or unwilling to sacrifice some wants for needs [or even other wants!] The problem wasn't that he reached for a better life; it was because he didn't have the foresight to make a budget. There is nothing wrong with working at a shoestore to make ends meet while pursuing your dream of being a writer. The fact that the writer would scoff at honest work that forces you to deal with people every day is just another mark against him. Retail is not pleasant work! He worked there; he knows! But he still decides to say, "But why should I, an educated, elite, be forced to dirty my hands serving the populace?" Believe it or not, without a piece of paper, you can be a successful writer. Or even just a fulfilled writer.
None of my fiction has been published anywhere but my blog [unless someone stole it that I'm unaware of], and I still would say I'm a writer. I didn't quit my job and burden everyone else with trying to cover for me. Also: There are PLENTY of careers that are not soul sucking jobs that people can go into to pay their bills and live modestly. The fact the author only sees finance as the same as scandalous is another air of elitist drivel.
Not only that, but the author makes it clear what his motivation is. It isn't to pursue writing for writing's sake. If he wanted that, he could have written for pulp magazines or whatever would take his stuff. No, what he wants is to use his writing to short cut his way to respectability and wealth: "But I have found, after some decades on this earth, that the road to character is often paved with family money and family connections, not to mention 14 percent effective tax rates on seven-figure incomes." Let me tell him this: I have no family money or connections, and I have a job that lets me afford my student debt, rent, other obligations and help where I see fit through charity or other means.
And I still write when I want to. All without being an elitist jack ass.