The author repeatedly expresses regret at having made poor financial decisions using the savings or debt as a metric. But it seems to me he has done quite well in fact: his daughters went to private schools, elite universities, had a nice wedding. What family, poor or well off, wouldn't sacrifice as much for their kids? Then he managed to stay true to his calling of a writer without compromising or cutting corners (this is a big one!). Look at the many quintessential immigrant families who used to be doctors or lawyers in their native countries who take up menial jobs to scrape by and still do a lot worse than the author. Or others who swallow their pride and go into more well-paid professions that they don't necessarily have passion for.

I'm probably lowering the standard of living target reasoning like this, which is not fair to the article which focuses on what middle class should be like, or was in the post-war boom decades. But still it could be a lot worse.