Tamara,
Just an idea for the Bigger timeline... Grant found after a couple of weeks that he preferred to write in the date first in his timeline box, followed by the name of the person or event. This let him see how much room was left for his picture.

I read through the timline box in the guide as written. Then, I'd tell him the date, the name, and remind him what he got to draw to go with it. You could also remind her that with the small boxes for her timeline, her drawings can be
really simple! Maybe if you let her know that the timline isn't for anyone else to look at and understand, but she (and you) can look back at it later and remember all the "heroes" you've read about this year and the way God used them in our country, it will let her enjoy it more.
I was totally a perfectionist as a child that didn't want to try anything I didn't think I could do perfectly.

I hated drawing anything for this reason...and now regret it. Comments like those I mentioned above are what have freed me up to be willing to enjoy something I can't do perfectly. (Unfortunately I was in college before I got over this.) My husband is great at this kind of "coaching" with our kids. When we were first married he even got me to play on a softball team with him (something I know I wasn't good at

). We had a blast, and I'm so glad that I can play with my kids now.
Keep at your encouragement with your little gal. You'll both be glad you did!

Kathleen