I'm the first year of what is broadly considered Gen Y and while most of what the writer articulates is highly subjective and biased, noting that she takes from the adage of how most women want a dad (read: leader to steer the ship) for a man, than a guy who feels he's owed it all. Still, she does have a point with the beginning which will be the only part I'll really address.
The illustration of "you're so special!" and "no one loses" is precisely what the generation I was born into had been raised with, and it's an utter farce. Someone who is special stands out, not blends in (everyone was taught that they're special which is simply a lie), and take a job for example, if you don't get the job and were "second best", you still lost -- you don't get a consolation job to be the second winner, you failed. Failure isn't inherently bad. It's supposed to teach a lesson, that's how you ultimately succeed after failure. This was reflected with grades where in order to fail in school you had to work just as hard for your F as you did your A. This type of coddling helped breed spoiled kids who have little initiative, think they're owed things without working hard, or harder than others.
Rest assured this is not the mentality my daughter will be raised with. Earning things, i.e. the initiative to go out and "do" or "accomplish" to me is extremely important, just as important as love, and as compassion.
Skimming that article I gathered that parents should be jerks to their children, and that we should except living mediocre lives, and not reach for goals. Was that supposed to be a sarcastic article? the author even contradicts herself sometimes.
I'm confused about contradiction, she's saying Gen Y has too many lazy people with embellished sense of ego and entitlement, quite the opposite of "not reaching for goals", and certainly nowhere near the straw man of parents needing to be jerks to their children.
Anyhow, I doubt people will see the underlying message, as this type of introspective criticism (of self and own generation) is generally not well received by most.