The advice my son got from several “experts” who helped him was “show, don’t tell”. It was very unnatural at first but he reworked the essays to really be more narrative and less declarative.
This article has some very useful tips: http://www.■■■■■■■■■■■■■■■■■/articles-and-advice/admission/articles/application-essay-clinic/how-use-dialogue-write-attention-grabbing-application-essay/
Kasami, the Yale supplemental essay essentially gives you the opportunity to write another CommonApp essay with a lower word limit. Treat it as such–just write about some sort of experience that aligns with you as a person. When I applied, I wrote about how I intellectually argued with my friends about whether Penderecki or Stockhausen wrote more dissonant music. Just show another side of you that explains why you’d be a good fit for their school without ever directly explaining why you would be.
IMO, the short takes were shortened to make them punchier and more fun. I see them as a snapshot–a way to get a quick, lighter look at the whole person. My kids didn’t spend a lot of time worrying about trying to impress admissions in 50 characters or less–they just said something that was concrete and true.