An important challenge or just too hard?

How do you know when something is just too hard for a kid?

This week the 8th graders are doing independent projects on the Civil War, doing nonfiction reading in order to answer questions that they chose. I ended up going with these questions:

Why did Lincoln free the slaves?
Was Lincoln "the great emancipator"?
Did the South have a chance?
What was it like to be a soldier?
What was the role of women in the war?
What was the role of African Americans in the war?

One kid, a kid I really like whose IEP says he has ADD, picked "Did the South have a chance?" Even though he was one of the kids we identified as needing a more straightforward question, I let him go with that question because he seemed really interested in it.

Yesterday he was reading a really cool Cobblestone article about submarines in the Civil War, but when I went over to him he was feeling really frustrated. He wasn't alone -- many kids felt overwhelmed by the task and confused about how to use the readings to answer the questions.

Anyway, with this kid, A.J., I could tell he was interested in the topic but felt like it was too hard. I said something like, "you know, A.J., this is a really tough question, but I think you can handle it." At first he protested, saying he wanted to switch to an easier question, but I persuaded him against it. I started asking him some scaffolding questions, like "what would it mean if the South had a chance?" He came up right away with, "they would have a better army, they would have more people, they would have more land," etc. He totally got the question. I said, "what about generals?" He said he didn't know. So I gave him an article about Civil War generals to read. He seemed better.

Today when we were working on the project again, he said "can you give me a different article? I'm switching over to 'what was it like to be a soldier.'" I felt defeated because 1) he still wanted to take the easy way out, and 2) he now expected me to choose the reading for him, which was contrary to the whole point of the exercise. I told him, "A.J., I know this is difficult for you and that you're feeling frustrated. But I wouldn't have encouraged you to do this if I didn't think you could." I reminded him of all the smart things he said yesterday. He seemed encouraged and grudgingly started work again on his original question.

I do believe he can do it, but he will probably have a much more difficult task than most of the other students. Is that fair? Am I wrong to keep pushing him toward that, when kids with much more experience with this kind of thing are getting away with easier questions? And what if I'm wrong and he can't do it? What kind of effect will that have on his confidence?