answered!!
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I like the first one much better. It happened over a longer time period, it required significant reflection on your part, and it is similar, I think to the kinds of challenges you may face in medical school. You also show humility in admitting your over-estimation of your capacity to handle the change in circumstances and the effect it had on other students.
What's the prompt?
#2 is for an integrity essay.
I'm less positive about #1; you're making excuses for failing in your responsibilities as a TA by adding all the additional noise about withdrawing from classes because of the death in the family. (I know this isn't a draft, so I'm going by what you're writing.) That said, I appreciate the "approach" that you tried and that it didn't work. I need a better focus with your set-up.
With 3000 characters, you can put in the context, but I advise you to be careful that the context does not dilute your answer or pose an unnecessary distraction as a back-door way to discuss academic troubles."Describe a time or situation where you have been unsuccessful or failed. (3000 characters)"
I think the context surrounding my failure is important, as my failure was not one of laziness or irresponsibility but rather communication, overconfidence in my abilities, and self-centeredness to the point that it hurts those I'm in service to, but I will definitely omit the withdrawals from the failure essay especially since there is often opportunity to address it elsewhere.
Would 2 work for "What is the toughest feedback you ever received? How did you handle it and what did you learn from it? (250 words)"? Feedback being from both the student (crying, frustration) and the volunteer coordinators (more concrete).
With 3000 characters, you can put in the context, but I advise you to be careful that the context does not dilute your answer or pose an unnecessary distraction as a back-door way to discuss academic troubles.
#2 doesn't work for feedback. The person is your student, not your supervisor or a leader. Telling you to give the student answers to justify him "checking out" is not feedback.