"How personal is too personal? How much information is too much information?"
When you're thinking about how much information to reveal, imagine yourself sitting down at an admission interview. The interviewer smiles and tells you to relax. Then he asks you your favorite books and secretly judges you if you answer "Heart of Darkness" (Liar, liar!). But the interviewer is still smiling, so you don't know he's beaming judgment rays at you. Your take a deep breath, compose yourself, and then answer his questions.
If this interviewer asks you an open-ended question about your experiences, would you talk to him about drugs, sex, violence, mayhem, and lawlessness? Probably not. I'm not saying you'd never have a good reason to discuss these experiences. (I am too lawyerly to pronounce such a broad edict.) But in most cases, you have little to gain from a confession that runs a high risk of having the reader judge you negatively. In an interview, at least you can clear up misunderstandings and read the other person's body language. But in an essay, which is really just a written interview, you don't get this chance. That's why essays (and emails, texts, and any other written communication) require more caution than interviews (and any oral communication).
If you want to write about something controversial, then try to figure out why that topic attracts you. If you can reveal the same aspect of your personality with a safer topic, then why risk putting off the reader with a controversial topic? A controversial topic can be a grimy window that obscures the reader's view of you. Before he can even see you, the dirt absorbs his attention. My general rule is that your topic should "do no harm" to your goal of illuminating your personality.
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Jon Perkins holds a B.A. in English from Stanford University and a J.D. from Harvard Law School. He helps students with their college, law school, and medical school applications.