Secondary: were you "required" to work during undergrad? Why was it necessary?

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I would recommend skipping this prompt. Just throw in one sentence or so saying that you worked for pay and why you did it (enjoyed the work, etc.).
 
I'm guessing that the question is trying to get at the idea of financial hardship during your time in college to get additional information about that experience (and, thus, how the adcom should view your application). Unless you're prepared to discuss significant financial hardship during college, I wouldn't use this prompt as an opportunity to talk about working for extra bar money.
 
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