My son used a singular “they” in his essays (as in “anybody who ever found themselves…”) and his English teacher (a middle-aged lady) suggested to change it to “he” everywhere. Now I’m wondering - should he make the changes and appear sexist? keep as is and appear ungrammatical? or write “himself or herself” and sound awkward?
Might need a little more context, but based on what you’ve provided, they seems more appropriate.
We’re the wrong ones to ask. Have a gander at what wiki notes from the style manuals. Some are older, but Wapo puts it this way: "…recommends trying to “write around the problem, perhaps by changing singulars to plurals, before using the singular they as a last resort” and specifically permits use of they for a “gender-nonconforming person”.
I’m sure someone will mention how language evolves. But this fir your college app. I’d rework the sentences, if possible.
Multiple choice quiz:
When a writer chooses a pronoun to reference a person of unknown gender, ____ may be making a possibly unintended political statement.
A. s/he
B. they
C. she
D. he
E. it
The “correct” answer depends on the admissions readers.
But yes, writing around it as mentioned in reply #2 can avoid having to guess what an admissions reader will see as “correct”:
When writers choose pronouns to reference a person of unknown gender, they may be making possibly unintended political statements.
Sorry, forgot the link.
https://en.wikipedia.org/wiki/Singular_they
A few essays went out already, with “they” I think. I hope at least UChicago wouldn’t mind either version 
I’ll tell him to avoid the dilemma in the RD wave.
Write around it – perhaps “all those who have ever found themselves”
Don’t worry about the apps already submitted. Adcoms know the trend to use “they.” It’s just a good idea to think about the options for the remaining apps.
Don’t overthink the issue. It really does not matter.
Until it sounds awkward. As apocryphally attributed to Winston Churchill about the “rule” of not ending sentences with a preposition, “This is the sort of English up with which I will not put,”
I would just use they, unless maybe it’s personal enough that it could be referring to you, and then maybe you could use your own gender? Most people probably will just read over it anyway. Depending on the school, it might be better to make a grammar mistake than a political statement or vice versa
On a related note…is it OK to use your own name in the essay? Will they see it on the rest of the application or is it separate somehow? I know sometimes for scholarships and things it says not to so that it’s anonymous/unbiased.
A valid question that deserves its own thread. Please don’t hijack a thread to ask.