Alexandra Petri, Give Legacies A Chance:

But being a legacy with thoughts of applying is a very specific kind of adversity.

Hmm, that doesn’t sound quite right. Let’s play around with it.

But being a legacy with thoughts of applying is a counterintuitive sort of adversity.

No, not right; too bulky. Shift the word order around a bit?

The legacy with thoughts of applying faces a counterintuitive sort of adversity.

Still, the tone seems off, too assured of itself. The sentence needs more qualifiers.

The legacy with thoughts of applying faces a counterintuitive sort of adversity, I suppose, if you squint really hard after a mescaline trip.

Maybe a metaphor thrown in there would help?

In much the same way that investment managers face the perilous difficulty of finding a dog-sitter while they vacation in the Hamptons, the legacy with thoughts of applying faces a counterintuitive sort of adversity, I suppose, if you squint really hard after a mescaline trip.

No, no, all wrong: clumsy and awkward. It really needs tightening up, not loosening. Back to the drawing board:

But being a legacy with thoughts of applying is a very specific kind of adversity not really an adversity at all.

Great. Send it to press.

Bonus nitpick: Legacy admits don’t even need to know the difference between the Dean of Admissions and the Director of Admissions, even though they have them over to dinner all the time! LoLLL!1